Journal article

Cholesteryl 6-O-acyl-alpha-glucosides from diverseHelicobacterspp. signal through the C-type lectin receptor Mincle

Dylan GM Smith, Emi Ito, Sho Yamasaki, Spencer J Williams

ORGANIC & BIOMOLECULAR CHEMISTRY | ROYAL SOC CHEMISTRY | Published : 2020

Abstract

Helicobacter spp. are Gram-negative bacteria that cause a spectrum of disease in the gut, biliary tree and liver. Many Helicobacter spp. produce a range of cholesteryl α-glucosides that have the potential to act as pathogen associated molecular patterns. We report a highly stereoselective α-glucosylation of cholesterol using 3,4,6-tri-O-acetyl-2-O-benzyl-D-glucopyranosyl N-phenyl-2,2,2-trifluoroacetimidate, which allowed the synthesis of cholesteryl α-glucoside (αCG) and representative Helicobacter spp. cholesteryl 6-O-acyl-α-glucosides (αCAGs; acyl = C12:0, 14:0, C16:0, C18:0, C18:1). All αCAGs, irrespective of the nature of their acyl chain composition, strongly agonised signalling through..

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University of Melbourne Researchers