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ID: ALA4043086
Journal: Bioorg Med Chem
Title: Facile access to pseudo-thio-1,2-dimannoside, a new glycomimetic DC-SIGN antagonist.
Authors: Tamburrini A, Achilli S, Vasile F, Sattin S, Vivès C, Colombo C, Fieschi F, Bernardi A.
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.
CiteXplore: 28389114