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-(β-D-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-β-D-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.
Short Regioselective Chemoenzymatic Synthesis and Biological Evaluation of 2-O-b-d-Sulfoquinovosylmonoacylglycerols / M.S. Dangate, L. Franchini, F.C.V. Ronchetti, T. Arai, A. Iida, H. Tokuda, D.R. Colombo. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 34:34(2009), pp. 6019-6026.
|Titolo:||Short Regioselective Chemoenzymatic Synthesis and Biological Evaluation of 2-O-b-d-Sulfoquinovosylmonoacylglycerols|
|Parole Chiave:||Antitumor agents; Enzyme catalysis; Glycolipids|
|Settore Scientifico Disciplinare:||Settore BIO/10 - Biochimica|
|Data di pubblicazione:||2009|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/ejoc.200900943|
|Appare nelle tipologie:||01 - Articolo su periodico|