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. [10.1002/ejoc.200900943]
Short Regioselective Chemoenzymatic Synthesis and Biological Evaluation of 2-O-b-d-Sulfoquinovosylmonoacylglycerols
M.S. Dangate;L. Franchini;F.C.V. Ronchetti;D.R. Colombo
2009
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-(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.Pubblicazioni consigliate
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