title: 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.
authors.affiliation: Universita' degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy.
authors.forename: Alice
authors.initials: A
authors.lastname: Tamburrini
authors.affiliation: Univ. Grenoble Alpes, CEA, CNRS, Institut de Biologie Structurale, F-38000 Grenoble, France.
authors.forename: Silvia
authors.initials: S
authors.lastname: Achilli
authors.affiliation: Universita' degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy.
authors.forename: Francesca
authors.initials: F
authors.lastname: Vasile
authors.affiliation: Universita' degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy.
authors.forename: Sara
authors.initials: S
authors.lastname: Sattin
authors.affiliation: Univ. Grenoble Alpes, CEA, CNRS, Institut de Biologie Structurale, F-38000 Grenoble, France.
authors.forename: Corinne
authors.initials: C
authors.lastname: Vivès
authors.affiliation: Universita' degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy.
authors.forename: Cinzia
authors.initials: C
authors.lastname: Colombo
authors.affiliation: Univ. Grenoble Alpes, CEA, CNRS, Institut de Biologie Structurale, F-38000 Grenoble, France.
authors.forename: Franck
authors.initials: F
authors.lastname: Fieschi
authors.affiliation: Universita' degli Studi di Milano, Dipartimento di Chimica, via Golgi 19, 20133 Milano, Italy. Electronic address: anna.bernardi@unimi.it.
authors.forename: Anna
authors.initials: A
authors.lastname: Bernardi
mesh_terms: D015815:Cell Adhesion Molecules / Q000037:antagonists & inhibitors* / Q000378:metabolism; D015195:Drug Design; D006801:Humans; D037181:Lectins, C-Type / Q000037:antagonists & inhibitors* / Q000378:metabolism; D008362:Mannosides / Q000737:chemistry* / Q000494:pharmacology*; D008958:Models, Molecular; D011956:Receptors, Cell Surface / Q000037:antagonists & inhibitors* / Q000378:metabolism; D020349:Surface Plasmon Resonance; D013865:Thioglycosides / Q000737:chemistry / Q000494:pharmacology; D000099215:DC-Specific ICAM-3 Grabbing Nonintegrin
chemical_list: D015815:Cell Adhesion Molecules; D037181:Lectins, C-Type; D008362:Mannosides; D011956:Receptors, Cell Surface; D013865:Thioglycosides; D000099215:DC-Specific ICAM-3 Grabbing Nonintegrin
keywords: DC-SIGN; Glycomimetics; Mannobioside; NOESY; Thioglycosides