Journal article
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, SJ Williams
Chemical Communications | ROYAL SOC CHEMISTRY | Published : 2016
DOI: 10.1039/c6cc05631h
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.
Grants
Awarded by Australian Research Council
Funding Acknowledgements
Funding was provided by the Australian Research Council, a JSPS Grant-in-Aid for Scientific Research, a Grant-in-Aid for Scientific Research on Innovative Areas (26110009) from MEXT, and Grants from MHLW and the Research on Development of New Drugs, AMED. SS thanks the Department of State Development, Business and Innovation of Victoria for a Victoria-India Doctoral Scholarship and the Australia India Institute. We thank Dr Mark Richardson for assistance in defining the stereochemistry of the products of the Jacobsen resolution.