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Article Dans Une Revue Bioorganic and Medicinal Chemistry Année : 2017

Facile access to pseudo-thio-1,2-dimannoside, a new glycomimetic DC-SIGN antagonist.

Résumé

The synthesis and conformational analysis of pseudo-thio-1,2-dimannoside are described. This molecule mimics mannobioside (Manα(1,2)Man) and is an analog of pseudo-1,2-dimannoside, with expected increased stability to enzymatic hydrolysis. A short and efficient synthesis was developed based on an epoxide ring-opening reaction by a mannosyl thiolate, generated in situ from the corresponding thioacetate. NMR-NOESY studies supported by MM3(∗) calculations showed that the pseudo-thio-1,2-dimannoside shares the conformational behavior of the pseudo-1,2-dimannoside and is a structural mimic of the natural disaccharide. Its affinity for DC-SIGN was measured by SPR and found to be comparable to the corresponding O-linked analog, offering good opportunities for further developments.

Dates et versions

hal-01561634 , version 1 (13-07-2017)

Identifiants

Citer

Alice Tamburrini, Silvia Achilli, Francesca Vasile, Sara Sattin, Corinne Vivès, et al.. Facile access to pseudo-thio-1,2-dimannoside, a new glycomimetic DC-SIGN antagonist.. Bioorganic and Medicinal Chemistry, 2017, pii: S0968-0896(17)30578-3, ⟨10.1016/j.bmc.2017.03.046⟩. ⟨hal-01561634⟩
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