Publications – Département de Chimie de l'ENS

@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}
}

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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.

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.

$alpha$-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.

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.

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.

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}
}

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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.

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 Article de journal

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}
}

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