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Bioorg Med Chem. 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.

Author information

1
Universita' degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy.
2
Univ. Grenoble Alpes, CEA, CNRS, Institut de Biologie Structurale, F-38000 Grenoble, France.
3
Universita' degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy. Electronic address: anna.bernardi@unimi.it.

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

PMID:
28389114
DOI:
10.1016/j.bmc.2017.03.046
[Indexed for MEDLINE]
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