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

Sayali Shah; Masahiro Nagata; Sho Yamasaki; Spencer J. Williams

doi:10.1039/c6cc05631h

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

Sayali Shah, Masahiro Nagata, Sho Yamasaki, Spencer J. Williams

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

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.

Original language	English
Pages (from-to)	10902-10905
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	72
DOIs	https://doi.org/10.1039/c6cc05631h
Publication status	Published - 2016

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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AU - Yamasaki, Sho

AU - Williams, Spencer J.

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N2 - 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.

AB - 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.

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

Abstract

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