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

Abstract : 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.
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Submitted on : Thursday, July 13, 2017 - 10:49:00 AM
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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 & medicinal chemistry, Elsevier, 2017, pii: S0968-0896(17)30578-3, 〈10.1016/j.bmc.2017.03.046〉. 〈hal-01561634〉



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