You will find below the list of publications of all the members of the Peptides, Glycoconjugates and Metals in Biology research pole. For individual or theme-specific publications, please consult the research or the personal pages via the members list using the sidebar navigation tool.
2003 |
A,Đ-Oligomethylenic capping of α- and β-cyclodextrins Article de journal T Lecourt; J -M Mallet; P Sinaÿ Comptes Rendus Chimie, 6 (1), p. 87–90, 2003. @article{Lecourt:2003a, title = {A,{D}-Oligomethylenic capping of α- and β-cyclodextrins}, author = {T Lecourt and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0038583942&doi=10.1016%2fS1631-0748%2803%2900005-5&partnerID=40&md5=b02812b0fd21c27d702ccd7d356dc612}, doi = {10.1016/S1631-0748(03)00005-5}, year = {2003}, date = {2003-01-01}, journal = {Comptes Rendus Chimie}, volume = {6}, number = {1}, pages = {87--90}, abstract = {α- and β-cyclodextrins have easily been converted into basket molecules, the handle being an oligomethylenic chain bridging A and D positions on the primary rim. The size of the handle influences the complexing properties of these cyclodextrins. © 2003 Acad\'{e}mie des sciences. Published by \'{E}ditions scientifiques et m\'{e}dicales Elsevier SAS. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } α- and β-cyclodextrins have easily been converted into basket molecules, the handle being an oligomethylenic chain bridging A and D positions on the primary rim. The size of the handle influences the complexing properties of these cyclodextrins. © 2003 Académie des sciences. Published by Éditions scientifiques et médicales Elsevier SAS. All rights reserved. |
Efficient Synthesis of Doubly Connected Primary Face-to-Face Cyclodextrin Homo-Dimers Article de journal T Lecourt; J -M Mallet; P Sinaÿ European Journal of Organic Chemistry, (23), p. 4553–4560, 2003. @article{Lecourt:2003b, title = {Efficient Synthesis of Doubly Connected Primary Face-to-Face Cyclodextrin Homo-Dimers}, author = {T Lecourt and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0345600801&doi=10.1002%2fejoc.200300267&partnerID=40&md5=f63189ddf053f237a138c6a46c43231c}, doi = {10.1002/ejoc.200300267}, year = {2003}, date = {2003-01-01}, journal = {European Journal of Organic Chemistry}, number = {23}, pages = {4553--4560}, abstract = {"Head-to-head" type α- and β-cyclodextrin homo-dimers in which the two primary rims are doubly ligated through alkyl chains have been synthesised in high yield by acyclic diene metathesis (ADM), followed by ring-closing metathesis (RCM). © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.}, keywords = {}, pubstate = {published}, tppubtype = {article} } "Head-to-head" type α- and β-cyclodextrin homo-dimers in which the two primary rims are doubly ligated through alkyl chains have been synthesised in high yield by acyclic diene metathesis (ADM), followed by ring-closing metathesis (RCM). © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003. |
Synthesis of new conformationally constrained pentasaccharides as molecular probes to investigate the biological activity of heparin Article de journal E Sisu; S Tripathy; J -M Mallet; P -A Driguez; J -P Hérault; P Sizun; J -M Herbert; M Petitou; P Sinay Biochimie, 85 (1-2), p. 91–99, 2003. @article{Sisu:2003, title = {Synthesis of new conformationally constrained pentasaccharides as molecular probes to investigate the biological activity of heparin}, author = {E Sisu and S Tripathy and J -M Mallet and P -A Driguez and J -P H\'{e}rault and P Sizun and J -M Herbert and M Petitou and P Sinay}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0037837504&doi=10.1016%2fS0300-9084%2803%2900054-3&partnerID=40&md5=f469db32849cf182d18534b9b9bf3b0e}, doi = {10.1016/S0300-9084(03)00054-3}, year = {2003}, date = {2003-01-01}, journal = {Biochimie}, volume = {85}, number = {1-2}, pages = {91--99}, abstract = {We have synthesized three new antithrombin activating pentasaccharides displaying various sulfation patterns on the reducing end unit (H). We found that when L-iduronic acid stands in the 2S0 conformation, the sulfate groups at positions 3 and 6 of the reducing end unit are practically devoid of influence on the activation of antithrombin. This suggests that the positive role of these sulfates is more related to their ability to shift the conformational equilibrium of L-iduronic acid towards 3S0 than to directly interact with the protein. © 2003 \'{E}ditions scientifiques et m\'{e}dicales Elsevier SAS and Soci\'{e}t\'{e} fran\c{c}aise de biochimie et biologie mol\'{e}culaire. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } We have synthesized three new antithrombin activating pentasaccharides displaying various sulfation patterns on the reducing end unit (H). We found that when L-iduronic acid stands in the 2S0 conformation, the sulfate groups at positions 3 and 6 of the reducing end unit are practically devoid of influence on the activation of antithrombin. This suggests that the positive role of these sulfates is more related to their ability to shift the conformational equilibrium of L-iduronic acid towards 3S0 than to directly interact with the protein. © 2003 Éditions scientifiques et médicales Elsevier SAS and Société française de biochimie et biologie moléculaire. All rights reserved. |
Transferred cross-relaxation and cross-correlation in NMR: Effects of intermediate exchange on the determination of the conformation of bound ligands Article de journal S Ravindranathan; J -M Mallet; P Sinay; G Bodenhausen Journal of Magnetic Resonance, 163 (2), p. 199–207, 2003. @article{Ravindranathan:2003a, title = {Transferred cross-relaxation and cross-correlation in NMR: Effects of intermediate exchange on the determination of the conformation of bound ligands}, author = {S Ravindranathan and J -M Mallet and P Sinay and G Bodenhausen}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0042531553&doi=10.1016%2fS1090-7807%2803%2900156-3&partnerID=40&md5=c182cd7c7d31fd4b7c83f71b4a3626ec}, doi = {10.1016/S1090-7807(03)00156-3}, year = {2003}, date = {2003-01-01}, journal = {Journal of Magnetic Resonance}, volume = {163}, number = {2}, pages = {199--207}, abstract = {Exchange transferred effects in solution-state NMR experiments allow one to determine the conformation of ligands that are weakly bound to macromolecules. Exchange-transferred nuclear Overhauser effect spectroscopy ('TR-NOESY') provides information about internuclear distances in a ligand in the bound state. Recently the possibility of obtaining dihedral angle information from a ligand in the bound state by exchange-transferred cross-correlation spectroscopy ('TR-CCSY') has been reported. In both cases the analysis of the signal amplitudes is usually based on the assumption that rapid exchange occurs between the free and bound forms of the ligand. In this paper we show that the fast exchange condition is not easily attained for observing exchange-transferred cross-correlation effects even in systems where exchange-transferred NOE can be observed. Extensive simulations based on analytical expressions for signal intensities corresponding to fast, intermediate, and slow chemical exchange have been carried out on a test system to determine the exchange regimes in which the fast exchange condition can be fulfilled for successfully implementing TR-NOESY and TR-CCSY. © 2003 Elsevier Science (USA). All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Exchange transferred effects in solution-state NMR experiments allow one to determine the conformation of ligands that are weakly bound to macromolecules. Exchange-transferred nuclear Overhauser effect spectroscopy ('TR-NOESY') provides information about internuclear distances in a ligand in the bound state. Recently the possibility of obtaining dihedral angle information from a ligand in the bound state by exchange-transferred cross-correlation spectroscopy ('TR-CCSY') has been reported. In both cases the analysis of the signal amplitudes is usually based on the assumption that rapid exchange occurs between the free and bound forms of the ligand. In this paper we show that the fast exchange condition is not easily attained for observing exchange-transferred cross-correlation effects even in systems where exchange-transferred NOE can be observed. Extensive simulations based on analytical expressions for signal intensities corresponding to fast, intermediate, and slow chemical exchange have been carried out on a test system to determine the exchange regimes in which the fast exchange condition can be fulfilled for successfully implementing TR-NOESY and TR-CCSY. © 2003 Elsevier Science (USA). All rights reserved. |
The Mannich Reaction of Hydrazones: Improved Reactivity under Solvent-Free Conditions Article de journal El L Kadbendm; L Gautier; L Grimaud; L M Harwood; V Michaut Green Chemistry, 5 (4), p. 477-477, 2003. @article{Kam:2003, title = {The Mannich Reaction of Hydrazones: Improved Reactivity under Solvent-Free Conditions}, author = {El L Kadbend{}m and L Gautier and L Grimaud and L M Harwood and V Michaut}, doi = {10.1039/b306242b}, year = {2003}, date = {2003-01-01}, journal = {Green Chemistry}, volume = {5}, number = {4}, pages = {477-477}, keywords = {}, pubstate = {published}, tppubtype = {article} } |
β-1,2- and α-1,2-Linked Oligomannosides Mediate Adherence of Candida albicans Blastospores to Human Enterocytes In Vitro Article de journal F Dalle; T Jouault; P A Trinel; J Esnault; J M Mallet; P D'Athis; D Poulain; A Bonnin Infection and Immunity, 71 (12), p. 7061–7068, 2003. @article{Dalle:2003, title = {β-1,2- and α-1,2-Linked Oligomannosides Mediate Adherence of Candida albicans Blastospores to Human Enterocytes In Vitro}, author = {F Dalle and T Jouault and P A Trinel and J Esnault and J M Mallet and P D'Athis and D Poulain and A Bonnin}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0344420124&doi=10.1128%2fIAI.71.12.7061-7068.2003&partnerID=40&md5=b71d05795100a59c29fe676e4a0332c5}, doi = {10.1128/IAI.71.12.7061-7068.2003}, year = {2003}, date = {2003-01-01}, journal = {Infection and Immunity}, volume = {71}, number = {12}, pages = {7061--7068}, abstract = {Candida albicans is a commensal dimorphic yeast of the digestive tract that causes hematogenously disseminated infections in immunocompromised individuals. Endogenous invasive candidiasis develops from C. albicans adhering to the intestinal epithelium. Adherence is mediated by the cell wall surface, a domain composed essentially of mannopyranosyl residues bound to proteins, the N-linked moiety of which comprises sequences of α-1,2- and β-1,2-linked mannose residues. β-1,2-linked mannosides are also associated with a glycolipid, phospholipomannan, at the C. albicans surface. In order to determine the roles of β-1,2 and α-1,2 oligomannosides in the C. albicans-enterocyte interaction, we developed a model of adhesion of C. albicans VW32 blastospores to the apical regions of differentiated Caco-2 cells. Preincubation of yeasts with monoclonal antibodies (MAbs) specific for α-1,2 and β-1,2 mannan epitopes resulted in a dose-dependent decrease in adhesion (50% of the control with a 60-μg/ml MAb concentration). In competitive assays β-1,2 and α-1,2 tetramannosides were the most potent carbohydrate inhibitors, with 50% inhibitory concentrations of 2.58 and 6.99 mM, respectively. Immunolocalization on infected monolayers with MAbs specific for α-1,2 and β-1,2 oligomannosides showed that these epitopes were shed from the yeast to the enterocyte surface. Taken together, our data indicate that α-1,2 and β-1,2 oligomannosides are involved in the C. albicans-enterocyte interaction and participate in the adhesion of the yeasts to the mucosal surface.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Candida albicans is a commensal dimorphic yeast of the digestive tract that causes hematogenously disseminated infections in immunocompromised individuals. Endogenous invasive candidiasis develops from C. albicans adhering to the intestinal epithelium. Adherence is mediated by the cell wall surface, a domain composed essentially of mannopyranosyl residues bound to proteins, the N-linked moiety of which comprises sequences of α-1,2- and β-1,2-linked mannose residues. β-1,2-linked mannosides are also associated with a glycolipid, phospholipomannan, at the C. albicans surface. In order to determine the roles of β-1,2 and α-1,2 oligomannosides in the C. albicans-enterocyte interaction, we developed a model of adhesion of C. albicans VW32 blastospores to the apical regions of differentiated Caco-2 cells. Preincubation of yeasts with monoclonal antibodies (MAbs) specific for α-1,2 and β-1,2 mannan epitopes resulted in a dose-dependent decrease in adhesion (50% of the control with a 60-μg/ml MAb concentration). In competitive assays β-1,2 and α-1,2 tetramannosides were the most potent carbohydrate inhibitors, with 50% inhibitory concentrations of 2.58 and 6.99 mM, respectively. Immunolocalization on infected monolayers with MAbs specific for α-1,2 and β-1,2 oligomannosides showed that these epitopes were shed from the yeast to the enterocyte surface. Taken together, our data indicate that α-1,2 and β-1,2 oligomannosides are involved in the C. albicans-enterocyte interaction and participate in the adhesion of the yeasts to the mucosal surface. |
2002 |
Synthesis of seven- and eight-membered carbasugar analogs via ring-closing metathesis and their inhibitory activities toward glycosidases Article de journal Y Blériot; A Giroult; J -M Mallet; E Rodriguez; P Vogel; P Sinaÿ Tetrahedron Asymmetry, 13 (23), p. 2553–2565, 2002. @article{Bleriot:2002b, title = {Synthesis of seven- and eight-membered carbasugar analogs via ring-closing metathesis and their inhibitory activities toward glycosidases}, author = {Y Bl\'{e}riot and A Giroult and J -M Mallet and E Rodriguez and P Vogel and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0037180575&doi=10.1016%2fS0957-4166%2802%2900654-7&partnerID=40&md5=cb0c6383a7048ce95ca49709b47d19d3}, doi = {10.1016/S0957-4166(02)00654-7}, year = {2002}, date = {2002-01-01}, journal = {Tetrahedron Asymmetry}, volume = {13}, number = {23}, pages = {2553--2565}, abstract = {An expeditious and efficient synthesis of new enantiopure polyhydroxylated seven- and eight-membered carbocycles is described starting from 2,3,5-tri-O-benzyl-D-arabinose. The key cyclization step involves ring closing metathesis of 1,8- and 1,9-dienes using Grubbs' catalyst. All of the new carbasugar analogs synthesized were evaluated as glycosidase inhibitors. Contrary to our expectations, (1S,2S,3R,4R,5R)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol which has the β-D-mannopyranose configuration for C(1)-C(5) inhibits α- and β-glucosidases, whereas its diepimer (1S,2S,3R,4S,5S)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol, which has the α-D-glucopyranose configuration, is not recognised by these enzymes. © 2002 Elsevier Science Ltd. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } An expeditious and efficient synthesis of new enantiopure polyhydroxylated seven- and eight-membered carbocycles is described starting from 2,3,5-tri-O-benzyl-D-arabinose. The key cyclization step involves ring closing metathesis of 1,8- and 1,9-dienes using Grubbs' catalyst. All of the new carbasugar analogs synthesized were evaluated as glycosidase inhibitors. Contrary to our expectations, (1S,2S,3R,4R,5R)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol which has the β-D-mannopyranose configuration for C(1)-C(5) inhibits α- and β-glucosidases, whereas its diepimer (1S,2S,3R,4S,5S)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol, which has the α-D-glucopyranose configuration, is not recognised by these enzymes. © 2002 Elsevier Science Ltd. All rights reserved. |
Symmetrical doubly connected head-to-head α-cyclodextrin dimers: A high yield synthesis of a novel type of neoglycolipid Article de journal T Lecourt; J -M Mallet; P Sinaÿ Tetrahedron Letters, 43 (32), p. 5533–5536, 2002. @article{Lecourt:2002, title = {Symmetrical doubly connected head-to-head α-cyclodextrin dimers: A high yield synthesis of a novel type of neoglycolipid}, author = {T Lecourt and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0037025763&doi=10.1016%2fS0040-4039%2802%2901125-5&partnerID=40&md5=7e5b72c38bf3a9d02318976ae1b860bb}, doi = {10.1016/S0040-4039(02)01125-5}, year = {2002}, date = {2002-01-01}, journal = {Tetrahedron Letters}, volume = {43}, number = {32}, pages = {5533--5536}, abstract = {A 'head-to-head' type α-cyclodextrin dimer, wherein the two primary rims are doubly ligated through alkyl chains, is synthesised in high yield using acyclic diene metathesis (ADM) followed by ring closing metathesis (RCM). © 2002 Elsevier Science Ltd. All rights reserved.}, keywords = {}, pubstate = {published}, tppubtype = {article} } A 'head-to-head' type α-cyclodextrin dimer, wherein the two primary rims are doubly ligated through alkyl chains, is synthesised in high yield using acyclic diene metathesis (ADM) followed by ring closing metathesis (RCM). © 2002 Elsevier Science Ltd. All rights reserved. |
$alpha$-Nitrohydrazones: Versatile Intermediates for Phosphonate Derivatives Formation from Primary Nitro Compounds Article de journal L El Kai"m; L Grimaud; N K Jana; C Tirla Tetrahedron letters, 43 (11), p. 2037-2038, 2002. @article{ElKaim:2002, title = {$alpha$-Nitrohydrazones: Versatile Intermediates for Phosphonate Derivatives Formation from Primary Nitro Compounds}, author = {L El Kai"m and L Grimaud and N K Jana and C Tirla}, year = {2002}, date = {2002-01-01}, journal = {Tetrahedron letters}, volume = {43}, number = {11}, pages = {2037-2038}, keywords = {}, pubstate = {published}, tppubtype = {article} } |
Studies towards the Synthesis of Fiproniltextregistered Analogues: Improved Decarboxylation of $alpha$-Hydrazonoacid Derivatives Article de journal J E Ancel; L El Kai"m; A Gadras; L Grimaud; N K Jana Tetrahedron letters, 43 (46), p. 8319-8321, 2002. @article{Ancel:2002, title = {Studies towards the Synthesis of Fiproniltextregistered Analogues: Improved Decarboxylation of $alpha$-Hydrazonoacid Derivatives}, author = {J E Ancel and L El Kai"m and A Gadras and L Grimaud and N K Jana}, year = {2002}, date = {2002-01-01}, journal = {Tetrahedron letters}, volume = {43}, number = {46}, pages = {8319-8321}, keywords = {}, pubstate = {published}, tppubtype = {article} } |
Synthetic analogues of β-1,2 oligomannosides prevent intestinal colonization by the pathogenic yeast Candida albicans Article de journal F Dromer; R Chevalier; B Sendid; L Improvisi; T Jouault; R Robert; J M Mallet; D Poulain Antimicrobial Agents and Chemotherapy, 46 (12), p. 3869–3876, 2002. @article{Dromer:2002, title = {Synthetic analogues of β-1,2 oligomannosides prevent intestinal colonization by the pathogenic yeast Candida albicans}, author = {F Dromer and R Chevalier and B Sendid and L Improvisi and T Jouault and R Robert and J M Mallet and D Poulain}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0036895520&doi=10.1128%2fAAC.46.12.3869-3876.2002&partnerID=40&md5=074a5bebe56ea29c65453cce441e039f}, doi = {10.1128/AAC.46.12.3869-3876.2002}, year = {2002}, date = {2002-01-01}, journal = {Antimicrobial Agents and Chemotherapy}, volume = {46}, number = {12}, pages = {3869--3876}, abstract = {The pathogenic yeast Candida albicans displays at its cell surface β-1,2 oligomannosides (β-1,2-Mans). In contrast to the ubiquitous α-Mans, β-1,2-Mans bind to galectin-3, a major endogenous lectin expressed on epithelial cells. The specific role of β-1,2-Mans in colonization of the gut by C. albicans was assessed in a mouse model. A selected virulent strain of C. albicans (expressing more β-1,2-Man epitopes) induced more intense and sustained colonization than an avirulent strain (expressing less β-1,2-Man epitopes). Synthetic (Σ) β- and α-linked tetramannosides with antigenicities that mimicked the antigenicities of C. albicans-derived oligomannosides were then constructed. Oral administration of Σβ-1,2-Man (30 mg/kg of body weight) prior to inoculation with the virulent strain resulted in almost complete eradication of yeasts from stool samples, whereas administration of Σα-Man at the same dose did not. As most cases of human systemic candidiasis are endogenous in origin, this first demonstration that a synthetic analogue of a yeast adhesin can prevent yeast colonization in the gut opens the possibility of new prophylactic strategies.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The pathogenic yeast Candida albicans displays at its cell surface β-1,2 oligomannosides (β-1,2-Mans). In contrast to the ubiquitous α-Mans, β-1,2-Mans bind to galectin-3, a major endogenous lectin expressed on epithelial cells. The specific role of β-1,2-Mans in colonization of the gut by C. albicans was assessed in a mouse model. A selected virulent strain of C. albicans (expressing more β-1,2-Man epitopes) induced more intense and sustained colonization than an avirulent strain (expressing less β-1,2-Man epitopes). Synthetic (Σ) β- and α-linked tetramannosides with antigenicities that mimicked the antigenicities of C. albicans-derived oligomannosides were then constructed. Oral administration of Σβ-1,2-Man (30 mg/kg of body weight) prior to inoculation with the virulent strain resulted in almost complete eradication of yeasts from stool samples, whereas administration of Σα-Man at the same dose did not. As most cases of human systemic candidiasis are endogenous in origin, this first demonstration that a synthetic analogue of a yeast adhesin can prevent yeast colonization in the gut opens the possibility of new prophylactic strategies. |
Further evidence for the critical role of a non-chair conformation of L-iduronic acid in the activation of antithrombin Article de journal J Kovensky; J -M Mallet; J Esnault; P -A Driguez; P Sizun; J -P Hérault; J -M Herbert; M Petitou; P Sinaÿ European Journal of Organic Chemistry, (21), p. 3595–3603, 2002. @article{Kovensky:2002, title = {Further evidence for the critical role of a non-chair conformation of L-iduronic acid in the activation of antithrombin}, author = {J Kovensky and J -M Mallet and J Esnault and P -A Driguez and P Sizun and J -P H\'{e}rault and J -M Herbert and M Petitou and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0036847440&doi=10.1002%2f1099-0690%28200211%292002%3a21%3c3595%3a%3aAID-EJOC3595%3e3.0.CO%3b2-F&partnerID=40&md5=193f71c852ca2f0800be781577476ef3}, doi = {10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F}, year = {2002}, date = {2002-01-01}, journal = {European Journal of Organic Chemistry}, number = {21}, pages = {3595--3603}, abstract = {L-iduronic acid, a conformationally flexible monosaccharide, imparts a remarkable protein adaptability to the glycosaminoglycans heparin, heparan sulfate, and dermatan sulfate. The pentasaccharide representing the antithrombin binding site of heparin contains one such L-iduronic acid residue, the conformation of which has been suspected for a long time to be a critical factor in the interaction with antithrombin. We have recently synthesized pentasaccharides containing an L-iduronic acid residue conformationally forced to exist within a restricted arc (2S0 ⇄ 2,5B ⇄ 5S1) of the overall pseudorotational circle. We could thus demonstrate that the 2S0 conformation is adopted upon binding to the protein. In the present work, we now describe the synthesis of a similar pentasaccharide containing a slightly more flexible L-iduronic acid unit with a three-atom bridge between C-2 and C5 of the hexopyranose ring. This pentasaccharide is a better activator of AT-III with respect to blood coagulation factor Xa inhibition. These results confirm that L-iduronic acid adopts an unusual non-chair conformation close to 2S0 and clearly explains how the unique conformational behavior of L-iduronic acid is the key to heparin's interaction with AT-III. © Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.}, keywords = {}, pubstate = {published}, tppubtype = {article} } L-iduronic acid, a conformationally flexible monosaccharide, imparts a remarkable protein adaptability to the glycosaminoglycans heparin, heparan sulfate, and dermatan sulfate. The pentasaccharide representing the antithrombin binding site of heparin contains one such L-iduronic acid residue, the conformation of which has been suspected for a long time to be a critical factor in the interaction with antithrombin. We have recently synthesized pentasaccharides containing an L-iduronic acid residue conformationally forced to exist within a restricted arc (2S0 ⇄ 2,5B ⇄ 5S1) of the overall pseudorotational circle. We could thus demonstrate that the 2S0 conformation is adopted upon binding to the protein. In the present work, we now describe the synthesis of a similar pentasaccharide containing a slightly more flexible L-iduronic acid unit with a three-atom bridge between C-2 and C5 of the hexopyranose ring. This pentasaccharide is a better activator of AT-III with respect to blood coagulation factor Xa inhibition. These results confirm that L-iduronic acid adopts an unusual non-chair conformation close to 2S0 and clearly explains how the unique conformational behavior of L-iduronic acid is the key to heparin's interaction with AT-III. © Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002. |
2001 |
New highly hydrophobic Lewis X glycolipids: Synthesis and monolayer behaviour Article de journal J Esnault; J -M Mallet; Y Zhang; P Sinaÿ; T Le Bouar; F Pincet; E Perez European Journal of Organic Chemistry, (2), p. 253–260, 2001. @article{Esnault:2001, title = {New highly hydrophobic Lewis X glycolipids: Synthesis and monolayer behaviour}, author = {J Esnault and J -M Mallet and Y Zhang and P Sina\"{y} and T Le Bouar and F Pincet and E Perez}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0035139027&partnerID=40&md5=7545b6c0c9545015adb18b635a1c8bfa}, year = {2001}, date = {2001-01-01}, journal = {European Journal of Organic Chemistry}, number = {2}, pages = {253--260}, abstract = {Two highly hydrophobic Lewis X glycolipids 2 and 3 were prepared. The glycoconjugate 2 was constructed in the following way: pentaerythrytol was used as a distributor on which three racemic phytol hydrophobic chains and a triethyleneglycol spacer β-glycosylated with the pentasaccharide Gal (β 1-4)[Fuc (α 1-3)] GlcNAc (β 1-3) Gal (β 1-4) Glc were anchored. The glycoconjugate 3 was constructed in a similar way, the sugar moiety being the trisaccharide Gal (β 1-4)[Fuc (α 1-3)] GlcNAc, the so-called Lewis X determinant. A triethyleneglycol spacer was used in order to introduce the mobility required for the study of single carbohydrate-carbohydrate interactions. Three phytyl chains increase the hydrophobicity of the lipid moiety compared to the natural ceramide glycolipid 1. These glycolipids display a liquid-expanded behaviour with a high compressibility in monolayer studies. These properties associated with a low solubility in water make them good candidates for the study of the interaction between two Lewis X functionalized vesicles.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Two highly hydrophobic Lewis X glycolipids 2 and 3 were prepared. The glycoconjugate 2 was constructed in the following way: pentaerythrytol was used as a distributor on which three racemic phytol hydrophobic chains and a triethyleneglycol spacer β-glycosylated with the pentasaccharide Gal (β 1-4)[Fuc (α 1-3)] GlcNAc (β 1-3) Gal (β 1-4) Glc were anchored. The glycoconjugate 3 was constructed in a similar way, the sugar moiety being the trisaccharide Gal (β 1-4)[Fuc (α 1-3)] GlcNAc, the so-called Lewis X determinant. A triethyleneglycol spacer was used in order to introduce the mobility required for the study of single carbohydrate-carbohydrate interactions. Three phytyl chains increase the hydrophobicity of the lipid moiety compared to the natural ceramide glycolipid 1. These glycolipids display a liquid-expanded behaviour with a high compressibility in monolayer studies. These properties associated with a low solubility in water make them good candidates for the study of the interaction between two Lewis X functionalized vesicles. |
S K Das; J -M Mallet; J Esnault; P -A Driguez; P Duchaussoy; P Sizun; J -P Herault; J -M Herbert; M Petitou; P Sinay Chemistry - A European Journal, 7 (22), p. 4821–4834, 2001. @article{Das:2001, title = {Synthesis of conformationally locked L-iduronic acid derivatives: Direct evidence for a critical role of the skew-boat 2S0 conformer in the activation of antithrombin by heparin}, author = {S K Das and J -M Mallet and J Esnault and P -A Driguez and P Duchaussoy and P Sizun and J -P Herault and J -M Herbert and M Petitou and P Sinay}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0035914639&doi=10.1002%2f1521-3765%2820011119%297%3a22%3c4821%3a%3aAID-CHEM4821%3e3.0.CO%3b2-N&partnerID=40&md5=6dd1ec79d1aec45994766b63eaa184e3}, doi = {10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N}, year = {2001}, date = {2001-01-01}, journal = {Chemistry - A European Journal}, volume = {7}, number = {22}, pages = {4821--4834}, abstract = {We have used organic synthesis to understand the role of L-iduronic acid conformational flexibility in the activation of antithrombin by heparin. Among known synthetic analogues of the genuine pentasaccharidic sequence representing the antithrombin binding site of heparin, we have selected as a reference compound the methylated anti-factor Xa pentasaccharide 1. As in the genuine original fragment, the single L-iduronic acid moiety of this molecule exists in water solution as an equilibrium between three conformers 1C4, 4C1 and 2S0. We have thus synthesized three analogues of 1, in which the L-iduronic acid unit is locked in one of these three fixed conformations. A covalent two atom bridge between carbon atoms two and five of L-iduronic acid was first introduced to lock the pseudorotational itinerary of the pyranoid ring around the 2S0 form. A key compound to achieve this connection was the D-glucose derivative 5 in which the H-5 hydrogen atom has been replaced by a vinyl group, which is a progenitor of the carboxylic acid. Selective manipulations of this molecule resulted in the 2S0-type pentasaccharide 23. Starting from the D-glucose derivative 28, a covalent two atom bridge was now built up between carbon atoms three and five to lock the L-iduronic acid moiety around the 1C4 chair form conformation, and the 1C4-type pentasaccharide 43 was synthesized. Finally the L-iduronic acid containing disaccharide 58 which, due to the presence of the methoxymethyl substituent at position five adopts a 4C1 conformation, was directly used to synthesize the 4C1-type pentasaccharide 61. The locked pentasaccharide 23 showed about the same activity as the reference compound 1 in an antithrombin-mediated anti-Xa assay, whereas the two pentasaccharides 43 and 61 displayed very low activity. These results clearly establish the critical importance of the 2S0 conformation of L-iduronic acid in the activation of antithrombin by heparin. © Wiley-VCH Verlag GmbH, 2001.}, keywords = {}, pubstate = {published}, tppubtype = {article} } We have used organic synthesis to understand the role of L-iduronic acid conformational flexibility in the activation of antithrombin by heparin. Among known synthetic analogues of the genuine pentasaccharidic sequence representing the antithrombin binding site of heparin, we have selected as a reference compound the methylated anti-factor Xa pentasaccharide 1. As in the genuine original fragment, the single L-iduronic acid moiety of this molecule exists in water solution as an equilibrium between three conformers 1C4, 4C1 and 2S0. We have thus synthesized three analogues of 1, in which the L-iduronic acid unit is locked in one of these three fixed conformations. A covalent two atom bridge between carbon atoms two and five of L-iduronic acid was first introduced to lock the pseudorotational itinerary of the pyranoid ring around the 2S0 form. A key compound to achieve this connection was the D-glucose derivative 5 in which the H-5 hydrogen atom has been replaced by a vinyl group, which is a progenitor of the carboxylic acid. Selective manipulations of this molecule resulted in the 2S0-type pentasaccharide 23. Starting from the D-glucose derivative 28, a covalent two atom bridge was now built up between carbon atoms three and five to lock the L-iduronic acid moiety around the 1C4 chair form conformation, and the 1C4-type pentasaccharide 43 was synthesized. Finally the L-iduronic acid containing disaccharide 58 which, due to the presence of the methoxymethyl substituent at position five adopts a 4C1 conformation, was directly used to synthesize the 4C1-type pentasaccharide 61. The locked pentasaccharide 23 showed about the same activity as the reference compound 1 in an antithrombin-mediated anti-Xa assay, whereas the two pentasaccharides 43 and 61 displayed very low activity. These results clearly establish the critical importance of the 2S0 conformation of L-iduronic acid in the activation of antithrombin by heparin. © Wiley-VCH Verlag GmbH, 2001. |
Ultraweak sugar-sugar interactions for transient cell adhesion Article de journal F Pincet; T L Bouar; Y Zhang; J Esnault; J -M Mallet; E Perez; P Sinaÿ Biophysical Journal, 80 (3), p. 1354–1358, 2001. @article{Pincet:2001, title = {Ultraweak sugar-sugar interactions for transient cell adhesion}, author = {F Pincet and T L Bouar and Y Zhang and J Esnault and J -M Mallet and E Perez and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-20644443266&doi=10.1016%2fS0006-3495%2801%2976108-5&partnerID=40&md5=ae83dd3860c40d1215e17aa630aa4ef1}, doi = {10.1016/S0006-3495(01)76108-5}, year = {2001}, date = {2001-01-01}, journal = {Biophysical Journal}, volume = {80}, number = {3}, pages = {1354--1358}, abstract = {Carbohydrate-carbohydrate interactions are rarely considered in biologically relevant situations such as cell recognition and adhesion. One Ca2+-mediated homotypic interaction between two Lewisx determinants (Lex) has been proposed to drive cell adhesion in murine embryogenesis. Here, we confirm the existence of this specific interaction by reporting the first direct quantitative measurements in an environment akin to that provided by membranes. The adhesion between giant vesicles functionalized with Lex was obtained by micropipette aspiration and contact angle measurements. This interaction is below the thermal energy, and cell-cell adhesion will require a large number of molecules, as illustrated by the Lex concentration peak observed at the cell membranes during the morula stage of the embryo. This adhesion is ultralow and therefore difficult to measure. Such small interactions explain why the concept of specific interactions between carbohydrates is often neglected.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Carbohydrate-carbohydrate interactions are rarely considered in biologically relevant situations such as cell recognition and adhesion. One Ca2+-mediated homotypic interaction between two Lewisx determinants (Lex) has been proposed to drive cell adhesion in murine embryogenesis. Here, we confirm the existence of this specific interaction by reporting the first direct quantitative measurements in an environment akin to that provided by membranes. The adhesion between giant vesicles functionalized with Lex was obtained by micropipette aspiration and contact angle measurements. This interaction is below the thermal energy, and cell-cell adhesion will require a large number of molecules, as illustrated by the Lex concentration peak observed at the cell membranes during the morula stage of the embryo. This adhesion is ultralow and therefore difficult to measure. Such small interactions explain why the concept of specific interactions between carbohydrates is often neglected. |
Synthesis of conformationally locked carbohydrates: A skew-boat conformation of L-iduronic acid governs the antithrombotic activity of heparin Article de journal S K Das; J -M Mallet; J Esnault; P -A Driguez; P Duchaussoy; P Sizun; J -P Hérault; J -M Herbert; M Petitou; P Sinaÿ Angewandte Chemie - International Edition, 40 (9), p. 1670–1673, 2001. @article{Das:2001a, title = {Synthesis of conformationally locked carbohydrates: A skew-boat conformation of L-iduronic acid governs the antithrombotic activity of heparin}, author = {S K Das and J -M Mallet and J Esnault and P -A Driguez and P Duchaussoy and P Sizun and J -P H\'{e}rault and J -M Herbert and M Petitou and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0035805327&doi=10.1002%2f1521-3773%2820010504%2940%3a9%3c1670%3a%3aAID-ANIE16700%3e3.0.CO%3b2-Q&partnerID=40&md5=001e36be44b70df1dab167587c5d7f1f}, doi = {10.1002/1521-3773(20010504)40:9<1670::AID-ANIE16700>3.0.CO;2-Q}, year = {2001}, date = {2001-01-01}, journal = {Angewandte Chemie - International Edition}, volume = {40}, number = {9}, pages = {1670--1673}, abstract = {Conformational flexibility of L-iduronic acid is a key feature of this typical component of heparin. Three pentasaccharides have now been synthesized, which are analogues of the active site of heparin and in which the single L-iduronic acid is conformationally locked in either the 1C4, 4C1, or 2S0 form. Only the 2S0 variant 1 was able to fully activate antithrombin inhibition of the blood coagulation factor Xa.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Conformational flexibility of L-iduronic acid is a key feature of this typical component of heparin. Three pentasaccharides have now been synthesized, which are analogues of the active site of heparin and in which the single L-iduronic acid is conformationally locked in either the 1C4, 4C1, or 2S0 form. Only the 2S0 variant 1 was able to fully activate antithrombin inhibition of the blood coagulation factor Xa. |
2000 |
Cascade rearrangements of polyunsaturated sugars: A novel approach to the synthesis of oligosaccharide mimetics Article de journal A J Pearce; R Chevalier; J -M Mallet; P Sinaÿ European Journal of Organic Chemistry, (12), p. 2203–2206, 2000. @article{Pearce:2000, title = {Cascade rearrangements of polyunsaturated sugars: A novel approach to the synthesis of oligosaccharide mimetics}, author = {A J Pearce and R Chevalier and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0033934706&partnerID=40&md5=d4739db58d2aeaa2f7d8f00a914ac3f5}, year = {2000}, date = {2000-01-01}, journal = {European Journal of Organic Chemistry}, number = {12}, pages = {2203--2206}, abstract = {The readily available tri-unsaturated trisaccharide 4 undergoes a stereoselective cascade of reductive rearrangements with TIBAL (triisobutylaluminium) to afford, after oxidative workup, the (1→4) ether- linked trisaccharide mimetics 3 and 10.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The readily available tri-unsaturated trisaccharide 4 undergoes a stereoselective cascade of reductive rearrangements with TIBAL (triisobutylaluminium) to afford, after oxidative workup, the (1→4) ether- linked trisaccharide mimetics 3 and 10. |
Carbocyclic ring closure of unsaturated S-, Se-, and C-aryl glycosides Article de journal M Sollogoub; J -M Mallet; P Sinaÿ Angewandte Chemie - International Edition, 39 (2), p. 362–364, 2000. @article{Sollogoub:2000, title = {Carbocyclic ring closure of unsaturated S-, Se-, and C-aryl glycosides}, author = {M Sollogoub and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0034677084&doi=10.1002%2f%28SICI%291521-3773%2820000117%2939%3a2%3c362%3a%3aAID-ANIE362%3e3.0.CO%3b2-1&partnerID=40&md5=b21ded5e6df54f0a1879234b08ad2ffc}, doi = {10.1002/(SICI)1521-3773(20000117)39:2<362::AID-ANIE362>3.0.CO;2-1}, year = {2000}, date = {2000-01-01}, journal = {Angewandte Chemie - International Edition}, volume = {39}, number = {2}, pages = {362--364}, abstract = {Triisobutylaluminum-promoted rearrangement of unsaturated glycosides containing electron-donating aglycons - such as C-aryl glycoside 1, or O-, S- , and Seglycosides - provides direct access to highly functionalized cyclohexane derivatives such as 2.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Triisobutylaluminum-promoted rearrangement of unsaturated glycosides containing electron-donating aglycons - such as C-aryl glycoside 1, or O-, S- , and Seglycosides - provides direct access to highly functionalized cyclohexane derivatives such as 2. |
One-step synthesis of disaccharide mimetics via tandem rearrangement of unsaturated disaccharides Article de journal A J Pearce; J -M Mallet; P Sinaÿ Heterocycles, 52 (2), p. 819–826, 2000. @article{Pearce:2000b, title = {One-step synthesis of disaccharide mimetics via tandem rearrangement of unsaturated disaccharides}, author = {A J Pearce and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0034143437&partnerID=40&md5=7e9e2762c789a07517cada06d84638b8}, year = {2000}, date = {2000-01-01}, journal = {Heterocycles}, volume = {52}, number = {2}, pages = {819--826}, abstract = {The unsaturated thioglycoside disaccharide (4)undergoes stereoselective tandem reductive rearrangement with TIBAL (triisobutylaluminium) to afford the (1→4) ether-linked disaccharide mimetics (1-3).}, keywords = {}, pubstate = {published}, tppubtype = {article} } The unsaturated thioglycoside disaccharide (4)undergoes stereoselective tandem reductive rearrangement with TIBAL (triisobutylaluminium) to afford the (1→4) ether-linked disaccharide mimetics (1-3). |
1999 |
Regioselective debenzylation of sugars using triisobutylaluminium Article de journal M Sollogoub; S K Das; J -M Mallet; P Sinaÿ Comptes Rendus de l'Academie des Sciences - Series IIc: Chemistry, 2 (7-8), p. 441–448, 1999. @article{Sollogoub:1999, title = {Regioselective debenzylation of sugars using triisobutylaluminium}, author = {M Sollogoub and S K Das and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0033163821&doi=10.1016%2fS1387-1609%2800%2988558-8&partnerID=40&md5=0911eff1a98bf1d272aedd261bdb0ac1}, doi = {10.1016/S1387-1609(00)88558-8}, year = {1999}, date = {1999-01-01}, journal = {Comptes Rendus de l'Academie des Sciences - Series IIc: Chemistry}, volume = {2}, number = {7-8}, pages = {441--448}, abstract = {Triisobutylaluminium has been shown to be a commercial reagent of choice for achieving regioselective mono-O-debenzylation of a variety of perbenzylated mono-and disaccharides. © 1999 Acad\'{e}mie des sciences/\'{E}ditions scientifiques et m\'{e}dicales Elsevier SAS.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Triisobutylaluminium has been shown to be a commercial reagent of choice for achieving regioselective mono-O-debenzylation of a variety of perbenzylated mono-and disaccharides. © 1999 Académie des sciences/Éditions scientifiques et médicales Elsevier SAS. |
Synthesis of the β-methyl glycoside of lacto-N-fucopentaose III Article de journal Y -M Zhang; J Esnault; J -M Mallet; P Sinaÿ Journal of Carbohydrate Chemistry, 18 (4), p. 419–427, 1999. @article{Zhang:1999, title = {Synthesis of the β-methyl glycoside of lacto-N-fucopentaose III}, author = {Y -M Zhang and J Esnault and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0033472744&doi=10.1080%2f07328309908544006&partnerID=40&md5=680c67f1c703ab5e9cf88980ffbdd894}, doi = {10.1080/07328309908544006}, year = {1999}, date = {1999-01-01}, journal = {Journal of Carbohydrate Chemistry}, volume = {18}, number = {4}, pages = {419--427}, abstract = {A total synthesis of the β;-methyl glycoside of lacto-N-fucopentaose III (1) is described. Phenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1 →4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (4), a key intermediate prepared by condensation of 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide (2) and phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (3), was glycosylated with ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (5) to give the trisaccharide donor 6, which, on coupling with methyl 2,6-di-O-benzyl-β-D-galactopyranosyl-(1 →4) 2,3,6-tri-O-benzyl-β-D-glucopyranoside (7), afforded the pentasaccharide 8. It was easily transformed into the target pentasaccharide 1 via hydrazinolysis, acetylation, O-deacetylation, and hydrogenolysis.}, keywords = {}, pubstate = {published}, tppubtype = {article} } A total synthesis of the β;-methyl glycoside of lacto-N-fucopentaose III (1) is described. Phenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1 →4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (4), a key intermediate prepared by condensation of 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide (2) and phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (3), was glycosylated with ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (5) to give the trisaccharide donor 6, which, on coupling with methyl 2,6-di-O-benzyl-β-D-galactopyranosyl-(1 →4) 2,3,6-tri-O-benzyl-β-D-glucopyranoside (7), afforded the pentasaccharide 8. It was easily transformed into the target pentasaccharide 1 via hydrazinolysis, acetylation, O-deacetylation, and hydrogenolysis. |
Synthesis of capsular polysaccharide oligomers of Salmonella typhi, bacteria originated from typhoid fever Article de journal L K Shi-Shun; J -M Mallet; M Moreau; P Sinaÿ Tetrahedron, 55 (49), p. 14043–14068, 1999. @article{Shi-Shun:1999, title = {Synthesis of capsular polysaccharide oligomers of Salmonella typhi, bacteria originated from typhoid fever}, author = {L K Shi-Shun and J -M Mallet and M Moreau and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0033521044&partnerID=40&md5=5b3ae5c6c69b57e58a0e6cacd81606dd}, year = {1999}, date = {1999-01-01}, journal = {Tetrahedron}, volume = {55}, number = {49}, pages = {14043--14068}, abstract = {The highly antigenic capsular polysaccharide of Salmonella typhi is a polysaccharide made out of N-acetyl D-galactosaminuronic acid units connected together through an α(1→4) linkage. Most of the hydroxyl groups at C-3 are acetylated. In order to determine the minimal size of fragments required for eliciting a significant immunological response, the corresponding di, tri, tetra and hexasaccharides have been chemically synthesized. The strategy is based on the use of anomeric S-xanthates of 2-azido-2-deoxy-D- galactopyranosyl derivatives as glycosyl donors. It has been shown that tetra and hexasaccharides are able to inhibit antibody binding by native polysaccharide.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The highly antigenic capsular polysaccharide of Salmonella typhi is a polysaccharide made out of N-acetyl D-galactosaminuronic acid units connected together through an α(1→4) linkage. Most of the hydroxyl groups at C-3 are acetylated. In order to determine the minimal size of fragments required for eliciting a significant immunological response, the corresponding di, tri, tetra and hexasaccharides have been chemically synthesized. The strategy is based on the use of anomeric S-xanthates of 2-azido-2-deoxy-D- galactopyranosyl derivatives as glycosyl donors. It has been shown that tetra and hexasaccharides are able to inhibit antibody binding by native polysaccharide. |
Synthesis of C-oligosaccharides that mimic their natural O-analogous immunodeterminants in binding to monoclonal immunoglobulins Article de journal Y -C Xin; Y -M Zhang; J -M Mallet; C P J Glaudemans; P Sinaÿ European Journal of Organic Chemistry, (2), p. 471–476, 1999. @article{Xin:1999, title = {Synthesis of C-oligosaccharides that mimic their natural O-analogous immunodeterminants in binding to monoclonal immunoglobulins}, author = {Y -C Xin and Y -M Zhang and J -M Mallet and C P J Glaudemans and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0032819669&partnerID=40&md5=80421a09306bd8ed5871607ae27f372f}, year = {1999}, date = {1999-01-01}, journal = {European Journal of Organic Chemistry}, number = {2}, pages = {471--476}, abstract = {We have stereoselectively synthesized the analogues of the methyl β- glycosides of (1 → 6)-β-D-galacto-oligosaccharides (up to tetrasaccharide), in which the interglycosidic oxygen atoms are replaced by a methylene group.}, keywords = {}, pubstate = {published}, tppubtype = {article} } We have stereoselectively synthesized the analogues of the methyl β- glycosides of (1 → 6)-β-D-galacto-oligosaccharides (up to tetrasaccharide), in which the interglycosidic oxygen atoms are replaced by a methylene group. |
Synthesis of a highly hydrophobic dimeric Lewis X containing glycolipid: A model for the study of homotypic carbohydrate-carbohydrate interaction Article de journal S Bregant; Y Zhang; J -M Mallet; A Brodzki; P Sinay Glycoconjugate Journal, 16 (12), p. 757–765, 1999. @article{Bregant:1999, title = {Synthesis of a highly hydrophobic dimeric Lewis X containing glycolipid: A model for the study of homotypic carbohydrate-carbohydrate interaction}, author = {S Bregant and Y Zhang and J -M Mallet and A Brodzki and P Sinay}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0033291560&doi=10.1023%2fA%3a1007115528216&partnerID=40&md5=0b17dda61899c3ef8cdf49aa7ec0e5eb}, doi = {10.1023/A:1007115528216}, year = {1999}, date = {1999-01-01}, journal = {Glycoconjugate Journal}, volume = {16}, number = {12}, pages = {757--765}, abstract = {This paper describes the synthesis of an octasaccharidic glycolipid 1 based on a stereo- and regioselective glycosylation between a Lewis X trisaccharidic donor and a pentasaccharidic accepter. A highly hydrophobic lipid moiety of e new type was selected, making the compound 1 a good candidate for the study of the interaction of Lewis X functionelised vesicles.}, keywords = {}, pubstate = {published}, tppubtype = {article} } This paper describes the synthesis of an octasaccharidic glycolipid 1 based on a stereo- and regioselective glycosylation between a Lewis X trisaccharidic donor and a pentasaccharidic accepter. A highly hydrophobic lipid moiety of e new type was selected, making the compound 1 a good candidate for the study of the interaction of Lewis X functionelised vesicles. |
1998 |
Titanium (IV) promoted rearrangement of 6-deoxy-hex-5-enopyranosides into cyclohexanones Article de journal M Sollogoub; J -M Mallet; P Sinaÿ Tetrahedron Letters, 39 (21), p. 3471–3472, 1998. @article{Sollogoub:1998, title = {Titanium (IV) promoted rearrangement of 6-deoxy-hex-5-enopyranosides into cyclohexanones}, author = {M Sollogoub and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0032555005&doi=10.1016%2fS0040-4039%2898%2900529-2&partnerID=40&md5=5431ef68773a238fe0c28b00d833e63c}, doi = {10.1016/S0040-4039(98)00529-2}, year = {1998}, date = {1998-01-01}, journal = {Tetrahedron Letters}, volume = {39}, number = {21}, pages = {3471--3472}, abstract = {The Lewis acid Ti(O(i)Pr)Cl3 was found to mediate under very mild conditions (-78 °C) the high-yielding (82-98%) rearrangement of benzylated 6-deoxy-hex-5-enopyranosides of the α-D-gluco, galacto and manno series into substituted cyclohexanones.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The Lewis acid Ti(O(i)Pr)Cl3 was found to mediate under very mild conditions (-78 °C) the high-yielding (82-98%) rearrangement of benzylated 6-deoxy-hex-5-enopyranosides of the α-D-gluco, galacto and manno series into substituted cyclohexanones. |
Stereoselective synthesis of α-C-L-fucopyranosyl containing C-disaccharides Article de journal E D Rekaï; G Rubinstenn; J -M Mallet; P Sinaÿ; S N Müller; B Giese Synlett, (8), p. 831–834, 1998. @article{Rekai:1998, title = {Stereoselective synthesis of α-C-L-fucopyranosyl containing C-disaccharides}, author = {E D Reka\"{i} and G Rubinstenn and J -M Mallet and P Sina\"{y} and S N M\"{u}ller and B Giese}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0002874188&doi=10.1055%2fs-1998-3138&partnerID=40&md5=9eb1a338edff9ea8fbbb4de3e1e52a42}, doi = {10.1055/s-1998-3138}, year = {1998}, date = {1998-01-01}, journal = {Synlett}, number = {8}, pages = {831--834}, abstract = {A variety of α-C-L-fucopyranosyl containing C-disaccharides were stereoselectively synthesized by radical coupling of phenyl 3,4-O-isopropylidene-Se-β-L-fucopyranoside onto an appropriate exo-methylene-sugar, which is temporarily tethered.}, keywords = {}, pubstate = {published}, tppubtype = {article} } A variety of α-C-L-fucopyranosyl containing C-disaccharides were stereoselectively synthesized by radical coupling of phenyl 3,4-O-isopropylidene-Se-β-L-fucopyranoside onto an appropriate exo-methylene-sugar, which is temporarily tethered. |
1997 |
Transfer reactions catalyzed by cyclodextrin glucosyltransferase using 4-thiomaltosyl and C-maltosyl fluorides as artificial donors Article de journal L Bornaghi; J -P Utille; E D Rekaï; J -M Mallet; P Sinaÿ; H Driguez Carbohydrate Research, 305 (3-4), p. 561–568, 1997. @article{Bornaghi:1997, title = {Transfer reactions catalyzed by cyclodextrin glucosyltransferase using 4-thiomaltosyl and C-maltosyl fluorides as artificial donors}, author = {L Bornaghi and J -P Utille and E D Reka\"{i} and J -M Mallet and P Sina\"{y} and H Driguez}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0001011603&doi=10.1016%2fS0008-6215%2897%2900262-0&partnerID=40&md5=07edcaebd2771c0e2b0892d739443cc4}, doi = {10.1016/S0008-6215(97)00262-0}, year = {1997}, date = {1997-01-01}, journal = {Carbohydrate Research}, volume = {305}, number = {3-4}, pages = {561--568}, abstract = {Cyclodextrin glycosyltransferase enzyme from Bacillus circulans catalyzed the effective conversion of 4-thio-α-maltosyl fluoride into cyclo- α-(1 → 42)-thiomalto -tetraoside, -pentaoside, -hexaoside and linear hemithiomaltooligosaccharides. However, under the same conditions, C-maltosyl fluoride afforded only linear modified maltotetraose, maltohexaose and maltooctaose in moderate yield.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Cyclodextrin glycosyltransferase enzyme from Bacillus circulans catalyzed the effective conversion of 4-thio-α-maltosyl fluoride into cyclo- α-(1 → 42)-thiomalto -tetraoside, -pentaoside, -hexaoside and linear hemithiomaltooligosaccharides. However, under the same conditions, C-maltosyl fluoride afforded only linear modified maltotetraose, maltohexaose and maltooctaose in moderate yield. |
Synthesis and anti-thrombin activity of a hexasaccharide corresponding to the binding site of dermatan sulfate to heparin cofactor II Article de journal P Bourhis; F Machetto; P Duchaussoy; J -P Hérault; J -M Mallet; J -M Herbert; M Petitou; P Sinaÿ Bioorganic and Medicinal Chemistry Letters, 7 (22), p. 2843–2846, 1997. @article{Bourhis:1997, title = {Synthesis and anti-thrombin activity of a hexasaccharide corresponding to the binding site of dermatan sulfate to heparin cofactor II}, author = {P Bourhis and F Machetto and P Duchaussoy and J -P H\'{e}rault and J -M Mallet and J -M Herbert and M Petitou and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0030665625&doi=10.1016%2fS0960-894X%2897%2910082-8&partnerID=40&md5=dfb13dba0abb3e26628b3c1aba0e87df}, doi = {10.1016/S0960-894X(97)10082-8}, year = {1997}, date = {1997-01-01}, journal = {Bioorganic and Medicinal Chemistry Letters}, volume = {7}, number = {22}, pages = {2843--2846}, abstract = {A new synthetic route is described toward the hexasaccharide representing the heparin cofactor II binding region of dermatan sulfate. The anti-thrombin activity of this synthetic hexasaccharide is reported here for the first time. This compound is about two hundred times less active than dermatan sulfate itself for its ability to inhibit thrombin via heparin cofactor II.}, keywords = {}, pubstate = {published}, tppubtype = {article} } A new synthetic route is described toward the hexasaccharide representing the heparin cofactor II binding region of dermatan sulfate. The anti-thrombin activity of this synthetic hexasaccharide is reported here for the first time. This compound is about two hundred times less active than dermatan sulfate itself for its ability to inhibit thrombin via heparin cofactor II. |
Synthesis and biological activity of a new anti-factor Xa pentasaccharide with a C-interglycosidic bond Article de journal A Helmboldt; M Petitou; J -M Mallet; J -P Hérault; J -C Lormeau; P A Driguez; J -M Herbert; P Sinaÿ Bioorganic and Medicinal Chemistry Letters, 7 (12), p. 1507–1510, 1997. @article{Helmboldt:1997, title = {Synthesis and biological activity of a new anti-factor Xa pentasaccharide with a C-interglycosidic bond}, author = {A Helmboldt and M Petitou and J -M Mallet and J -P H\'{e}rault and J -C Lormeau and P A Driguez and J -M Herbert and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0031011624&doi=10.1016%2fS0960-894X%2897%2900252-7&partnerID=40&md5=2883038ae790b0d9bae3deeece735a02}, doi = {10.1016/S0960-894X(97)00252-7}, year = {1997}, date = {1997-01-01}, journal = {Bioorganic and Medicinal Chemistry Letters}, volume = {7}, number = {12}, pages = {1507--1510}, abstract = {A mixed synthetic C, O-pentasaccharide 17 has been synthesized and shown to display an anti-factor Xa activity similar to that of the corresponding O-pentasaccharide 18. 17 represents the first example of a synthetic C-oligosaccharidic mimetic eliciting a significant biological response.}, keywords = {}, pubstate = {published}, tppubtype = {article} } A mixed synthetic C, O-pentasaccharide 17 has been synthesized and shown to display an anti-factor Xa activity similar to that of the corresponding O-pentasaccharide 18. 17 represents the first example of a synthetic C-oligosaccharidic mimetic eliciting a significant biological response. |
Novel Carbocyclic Ring Closure of Hex-5-enopyranosides Article de journal S K Das; J -M Mallet; P Sinaÿ Angewandte Chemie (International Edition in English), 36 (5), p. 493–496, 1997. @article{Das:1997, title = {Novel Carbocyclic Ring Closure of Hex-5-enopyranosides}, author = {S K Das and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0030903538&doi=10.1002%2fanie.199704931&partnerID=40&md5=800d7644a0888deb9f9f9531de0bf885}, doi = {10.1002/anie.199704931}, year = {1997}, date = {1997-01-01}, journal = {Angewandte Chemie (International Edition in English)}, volume = {36}, number = {5}, pages = {493--496}, keywords = {}, pubstate = {published}, tppubtype = {article} } |