6-Deoxy-6-fluoro galactofuranosides: regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity | Zendy

Jeane Vaugenot | Zendy; Abderrafek El Harras | Zendy; Olivier Tasseau | Zendy; Rémi Marchal | Zendy; Laurent Legentil | Zendy; Boris Le Guennic | Zendy; Thierry Benvegnu | Zendy; Vincent Ferrières | Zendy

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6-Deoxy-6-fluoro galactofuranosides: regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity

Author(s) -

Jeane Vaugenot,

Abderrafek El Harras,

Olivier Tasseau,

Rémi Marchal,

Laurent Legentil,

Boris Le Guennic,

Thierry Benvegnu,

Vincent Ferrières

Publication year - 2020

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/c9ob02596k

Subject(s) - glycosylation , regioselectivity , chemistry , leishmania , stereochemistry , organic chemistry , biochemistry , computer science , catalysis , parasite hosting , world wide web

Selective glycosylation of the C-6 fluorinated galactofuranosyl acceptor 2 was studied with four galactofuranosyl donors. It was highlighted that this electron-withdrawing atom strongly impacted the behavior of the acceptor, thus leading to unprecedented glycosylation pathways. Competition between expected glycosylation of 2, ring expansion of this acceptor and furanosylation, and intermolecular aglycon transfer was observed. Further investigation of the fluorinated synthetic compounds showed that the presence of fluorine atom contributed to increase the inhibition of the growth of Leishmania tarentolae, a non-pathogenic strain of Leishmania.

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