Data di Pubblicazione:
2017
Citazione:
Facile access to pseudo-thio-1,2-dimannoside, a new glycomimetic DC-SIGN antagonist / A. Tamburrini, S. Achilli, F. Vasile, S. Sattin, C. Vivès, C. Colombo, F. Fieschi, A. Bernardi. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 1464-3391. - 25:19(2017 Oct 01), pp. 5142-5147. [10.1016/j.bmc.2017.03.046]
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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
DC-SIGN; Glycomimetics; Mannobioside; NOESY; Thioglycosides
Elenco autori:
A. Tamburrini, S. Achilli, F. Vasile, S. Sattin, C. Vivès, C. Colombo, F. Fieschi, A. Bernardi
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