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Short regioselective chemoenzymatic synthesis and biological evaluation of 1- O-Acyl-2- O-(β-D-sulfoquinovopyranosyl)-sn-glycerols
, L. Franchini, F. Ronchetti, T. Arai, A. Iida, H. Tokuda, D. Colombo
Published in
2009
   
Issue: 34
Pages: 6019 - 6026
Abstract
A convenient chemoenzymatic synthesis of a new class of non-natural sulfo-glycolipids - 2-O-(β-D-sulfoquinovosyl)monoacylglycerols (2-O-β-D-SQMG) - derived from 2-O-(βD-glucopyranosyl)glycerol and carrying acyl chains of various lengths at the 1-position of the sn-glycerol moiety, was performed with the aid of a key step involving regioselective lipase-catalyzed acylation of 2-O-(6-deoxy-6-tosyl-βD-glucopyranosyl)-sn- glycerol (4) at its 1-position, reported here for the first time. Elaboration of the sugar moiety through thioacetate substitution of the selectively inserted tosyl group with subsequent Oxone®oxidation in the presence of unprotected primary and secondary hydroxy groups efficiently afforded the target: compounds, the hexanoyl, dodecanoyl, and octadecanoyl derivatives 1a-c, which were active when tested in the EBV-EA in vitro assay for antitumor promoters. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
About the journal
JournalEuropean Journal of Organic Chemistry
ISSN1434193X