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. 2017 Oct 1;25(19):5142-5147.
doi: 10.1016/j.bmc.2017.03.046. Epub 2017 Mar 22.

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

Alice Tamburrini  1 , Silvia Achilli  2 , Francesca Vasile  1 , Sara Sattin  1 , Corinne Vivès  2 , Cinzia Colombo  1 , Franck Fieschi  2 , Anna Bernardi  3
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Free article

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

Alice Tamburrini et al. Bioorg Med Chem. .
Free article

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.

Keywords: DC-SIGN; Glycomimetics; Mannobioside; NOESY; Thioglycosides.

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