Issue 72, 2016

Total synthesis of a cyclopropane-fatty acid α-glucosyl diglyceride from Lactobacillus plantarum and identification of its ability to signal through Mincle

Abstract

We report a concise synthesis of glycolipid GL1 from Lactobacillus plantarum commencing from methyl α-D-glucopyroside. A Jacobsen hydrolytic kinetic resolution is used to generate a diastereomerically-pure glycidyl glucoside that was elaborated to the diglyceride by stepwise brominolysis, acylation with oleoyl chloride, and bromide-substitution by the tetrabutylammonium salt of 9S,10R-dihydrosterculic acid. GL1 and analogues were shown to signal through the glycolipid pattern recognition receptor Mincle.

Graphical abstract: Total synthesis of a cyclopropane-fatty acid α-glucosyl diglyceride from Lactobacillus plantarum and identification of its ability to signal through Mincle

Supplementary files

Article information

Article type
Communication
Submitted
08 Jul 2016
Accepted
08 Aug 2016
First published
12 Aug 2016

Chem. Commun., 2016,52, 10902-10905

Total synthesis of a cyclopropane-fatty acid α-glucosyl diglyceride from Lactobacillus plantarum and identification of its ability to signal through Mincle

S. Shah, M. Nagata, S. Yamasaki and S. J. Williams, Chem. Commun., 2016, 52, 10902 DOI: 10.1039/C6CC05631H

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