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.
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} } |
Radical mediated synthesis of N-acetyl-Đ-galactosamine containing C-disaccharides via a temporary phosphoramidic connection Article de journal G Rubinstenn; J Esnault; J -M Mallet; P Sinaÿ Tetrahedron Asymmetry, 8 (8), p. 1327–1336, 1997. @article{Rubinstenn:1997a, title = {Radical mediated synthesis of N-acetyl-{D}-galactosamine containing C-disaccharides via a temporary phosphoramidic connection}, author = {G Rubinstenn and J Esnault and J -M Mallet and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0030934796&doi=10.1016%2fS0957-4166%2897%2900141-9&partnerID=40&md5=0a6da893218460f0d70ef4aa9178c3b4}, doi = {10.1016/S0957-4166(97)00141-9}, year = {1997}, date = {1997-01-01}, journal = {Tetrahedron Asymmetry}, volume = {8}, number = {8}, pages = {1327--1336}, abstract = {The C-disaccharide α-D-GalNAc-C-(1→4)-β-D-Glc-OMe and its interglycosidic β anomer were synthesized by radical coupling of phenyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside onto methyl 2,6-di-O-benzyl-4-deoxy-4-C-methylene- β-D-xylo-hexopyranoside, which are temporarily connected through a phosphoramido tether. A similar reaction was performed with methyl 2,3-di-O-benzyl-4-deoxy-4-C-methylene-α-D-xylo-hexopyranoside to produce the two closely related α-OMe C-disaccharides.}, keywords = {}, pubstate = {published}, tppubtype = {article} } The C-disaccharide α-D-GalNAc-C-(1→4)-β-D-Glc-OMe and its interglycosidic β anomer were synthesized by radical coupling of phenyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-1-seleno-α-D-galactopyranoside onto methyl 2,6-di-O-benzyl-4-deoxy-4-C-methylene- β-D-xylo-hexopyranoside, which are temporarily connected through a phosphoramido tether. A similar reaction was performed with methyl 2,3-di-O-benzyl-4-deoxy-4-C-methylene-α-D-xylo-hexopyranoside to produce the two closely related α-OMe C-disaccharides. |
1996 |
L-Iduronic acid derivatives as glycosyl donors Article de journal C Tabeur; F Machetto; J -M Mallet; P Duchaussoy; M Petitou; P Sinaÿ Carbohydrate Research, 281 (2), p. 253–276, 1996. @article{Tabeur:1996, title = {L-Iduronic acid derivatives as glycosyl donors}, author = {C Tabeur and F Machetto and J -M Mallet and P Duchaussoy and M Petitou and P Sina\"{y}}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0030047169&doi=10.1016%2f0008-6215%2895%2900346-0&partnerID=40&md5=7c975943a9fe15de4dc6c277a0ac87ba}, doi = {10.1016/0008-6215(95)00346-0}, year = {1996}, date = {1996-01-01}, journal = {Carbohydrate Research}, volume = {281}, number = {2}, pages = {253--276}, abstract = {O-[Methyl (2-O-acetyl-3-O-benzyl-4-O-levulinyl-α, and β-L-idopyranosid)uronate]trichloroacetimidate and the corresponding n-pentenyl glycosides are efficient L-iduronic acid glycosyl donors. Both have been used for the high-yielding synthesis of basic disaccharide blocks which are useful for the subsequent synthesis of complex oligosaccharides related to heparin/heparan sulfate, and dermatan sulfate. In contrast, the corresponding thioethyl glycosides, thiophenyl glycosides, and fluoride, did not yield the expected disaccharides.}, keywords = {}, pubstate = {published}, tppubtype = {article} } O-[Methyl (2-O-acetyl-3-O-benzyl-4-O-levulinyl-α, and β-L-idopyranosid)uronate]trichloroacetimidate and the corresponding n-pentenyl glycosides are efficient L-iduronic acid glycosyl donors. Both have been used for the high-yielding synthesis of basic disaccharide blocks which are useful for the subsequent synthesis of complex oligosaccharides related to heparin/heparan sulfate, and dermatan sulfate. In contrast, the corresponding thioethyl glycosides, thiophenyl glycosides, and fluoride, did not yield the expected disaccharides. |
1994 |
Preparative scale synthesis of O-glycosides and of a disaccharide by electrochemical oxidation of phenyl S-glycosides Article de journal C Amatore; A Jutand; G Meyer; P Bourhis; F Machetto; J -M Mallet; P Sinaÿ; C Tabeur; Y -M Zhang Journal of Applied Electrochemistry, 24 (8), p. 725–729, 1994. @article{Amatore:1994, title = {Preparative scale synthesis of O-glycosides and of a disaccharide by electrochemical oxidation of phenyl S-glycosides}, author = {C Amatore and A Jutand and G Meyer and P Bourhis and F Machetto and J -M Mallet and P Sina\"{y} and C Tabeur and Y -M Zhang}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0028481742&doi=10.1007%2fBF00578086&partnerID=40&md5=d1acda1de0415e8d3faef46669c6db7d}, doi = {10.1007/BF00578086}, year = {1994}, date = {1994-01-01}, journal = {Journal of Applied Electrochemistry}, volume = {24}, number = {8}, pages = {725--729}, abstract = {O-glycosides were synthesized by electrochemical oxidation of phenyl S-glycosides in the presence of primary alcohols in acetonitrile. Similarly, a β-linked disaccharide was obtained selectively by oxidation of phenyl S-glycoside in the presence of a sugar alcohol. Electrosyntheses were performed under controlled potential or at constant current, in an undivided cell, on a large scale. 1 to 60 g of phenyl S-glycosides in 0.5 to 1 dm3 of acetonitrile were converted with chemical yields in the range of 65-75%. © 1994 Chapman & Hall.}, keywords = {}, pubstate = {published}, tppubtype = {article} } O-glycosides were synthesized by electrochemical oxidation of phenyl S-glycosides in the presence of primary alcohols in acetonitrile. Similarly, a β-linked disaccharide was obtained selectively by oxidation of phenyl S-glycoside in the presence of a sugar alcohol. Electrosyntheses were performed under controlled potential or at constant current, in an undivided cell, on a large scale. 1 to 60 g of phenyl S-glycosides in 0.5 to 1 dm3 of acetonitrile were converted with chemical yields in the range of 65-75%. © 1994 Chapman & Hall. |
The use of selenophenyl galactopyranosides for the synthesis of α and β-(1→4)-C-disaccharides Article de journal A Mallet; J -M Mallet; P Sinay Tetrahedron: Asymmetry, 5 (12), p. 2593–2608, 1994. @article{Mallet:1994, title = {The use of selenophenyl galactopyranosides for the synthesis of α and β-(1→4)-C-disaccharides}, author = {A Mallet and J -M Mallet and P Sinay}, url = {https://www.scopus.com/inward/record.uri?eid=2-s2.0-0027973192&doi=10.1016%2fS0957-4166%2800%2980403-6&partnerID=40&md5=0eb15610c7968e84c3322f7013b13f61}, doi = {10.1016/S0957-4166(00)80403-6}, year = {1994}, date = {1994-01-01}, journal = {Tetrahedron: Asymmetry}, volume = {5}, number = {12}, pages = {2593--2608}, abstract = {Methyl α-C-lactoside β-D-Gilp-C-(1→4)-α-D-Glcp-OMe and its α anomer were expeditiously synthesized by radical coupling of various selenophenyl galactopyranosides onto methyl 2,3-di-O-benzyl-4-deoxy-4-C-methylene-α-D-xylo-hexopyranoside, which aretemporarily connected through a silaketal tether. © 1994.}, keywords = {}, pubstate = {published}, tppubtype = {article} } Methyl α-C-lactoside β-D-Gilp-C-(1→4)-α-D-Glcp-OMe and its α anomer were expeditiously synthesized by radical coupling of various selenophenyl galactopyranosides onto methyl 2,3-di-O-benzyl-4-deoxy-4-C-methylene-α-D-xylo-hexopyranoside, which aretemporarily connected through a silaketal tether. © 1994. |
0000 |
A di-Copper Peptidyl Complex Mimics the Activity of Catalase, a Key Antioxidant Metalloenzyme Article de journal Koudedja Coulibaly; Marion Thauvin; Adyn Melenbacher; Clara Testard; Evangelia Trigoni; Amandine Vincent; Martin J Stillman; Sophie Vriz; Clotilde Policar; Nicolas Delsuc Inorganic Chemistry, 0 (0), p. null, 0000, (PMID: 34109781). @article{doi:10.1021/acs.inorgchem.0c03718, title = {A di-Copper Peptidyl Complex Mimics the Activity of Catalase, a Key Antioxidant Metalloenzyme}, author = {Koudedja Coulibaly and Marion Thauvin and Adyn Melenbacher and Clara Testard and Evangelia Trigoni and Amandine Vincent and Martin J Stillman and Sophie Vriz and Clotilde Policar and Nicolas Delsuc}, url = {https://doi.org/10.1021/acs.inorgchem.0c03718}, doi = {10.1021/acs.inorgchem.0c03718}, year = {0000}, date = {0000-01-01}, journal = {Inorganic Chemistry}, volume = {0}, number = {0}, pages = {null}, abstract = {Catalases (CAT) are antioxidant metalloenzymes necessary for life in oxygen-metabolizing cells to regulate H2O2 concentration by accelerating its dismutation. Many physiopathological situations are associated with oxidative stress resulting from H2O2 overproduction, during which antioxidant defenses are overwhelmed. We have used a combinatorial approach associated with an activity-based screening to discover a first peptidyl di-copper complex mimicking CAT. The complex was studied in detail and characterized for its CAT activity both in solutions and in cells using different analytical methods. The complex exhibited CAT activity in solutions and, more interestingly, on HyPer HeLa cells that possess a genetically encoded ratiometric fluorescent sensors of H2O2. These results highlight the efficiency of a combinatorial approach for the discovery of peptidyl complexes that exhibit catalytic activity.}, note = {PMID: 34109781}, keywords = {}, pubstate = {published}, tppubtype = {article} } Catalases (CAT) are antioxidant metalloenzymes necessary for life in oxygen-metabolizing cells to regulate H2O2 concentration by accelerating its dismutation. Many physiopathological situations are associated with oxidative stress resulting from H2O2 overproduction, during which antioxidant defenses are overwhelmed. We have used a combinatorial approach associated with an activity-based screening to discover a first peptidyl di-copper complex mimicking CAT. The complex was studied in detail and characterized for its CAT activity both in solutions and in cells using different analytical methods. The complex exhibited CAT activity in solutions and, more interestingly, on HyPer HeLa cells that possess a genetically encoded ratiometric fluorescent sensors of H2O2. These results highlight the efficiency of a combinatorial approach for the discovery of peptidyl complexes that exhibit catalytic activity. |