title: 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.
authors.affiliation: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Victoria 3010, Australia. sjwill@unimelb.edu.au.
authors.forename: Sayali
authors.initials: S
authors.lastname: Shah
authors.forename: Masahiro
authors.initials: M
authors.lastname: Nagata
authors.forename: Sho
authors.initials: S
authors.lastname: Yamasaki
authors.forename: Spencer J
authors.initials: SJ
authors.lastname: Williams
mesh_terms: D000818:Animals; D003521:Cyclopropanes / Q000737:chemistry*; D004075:Diglycerides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D005227:Fatty Acids / Q000737:chemistry*; D017930:Genes, Reporter; D006801:Humans; D048191:Lactiplantibacillus plantarum / Q000378:metabolism*; D037181:Lectins, C-Type / Q000235:genetics / Q000378:metabolism; D008565:Membrane Proteins / Q000235:genetics / Q000378:metabolism; D051379:Mice; D050778:NFATC Transcription Factors / Q000235:genetics; D017452:Receptors, IgG / Q000235:genetics / Q000378:metabolism; D015398:Signal Transduction; D013237:Stereoisomerism
chemical_list: C011439:1,2-diacylglycerol; C113583:Clecsf8 protein, mouse; D003521:Cyclopropanes; D004075:Diglycerides; D005227:Fatty Acids; D037181:Lectins, C-Type; D008565:Membrane Proteins; D050778:NFATC Transcription Factors; D017452:Receptors, IgG; C030797:cyclopropane