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Short Regioselective Chemoenzymatic Synthesis and Biological Evaluation of 1‐ O ‐Acyl‐2‐ O ‐(β‐ D ‐sulfoquinovopyranosyl)‐ sn ‐glycerols
Author(s) -
Dangate Milind,
Franchini Laura,
Ronchetti Fiamma,
Arai Takanari,
Iida Akira,
Tokuda Harukuni,
Colombo Diego
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900943
Subject(s) - chemistry , regioselectivity , moiety , tosyl , acylation , glycerol , acyl group , stereochemistry , lipase , chemical synthesis , glycolipid , organic chemistry , catalysis , enzyme , in vitro , biochemistry , group (periodic table)
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 ofvarious 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)