Journal article

α-Glucuronosyl and α-Glucosyl Diacylglycerides, Natural Killer T Cell-Activating Lipids from Bacteria and Fungi

SATVIKA BURUGUPALLI, CATARINA DOS SANTOS SA E ALMEIDA, Dylan GM Smith, SAYALI SHAH, ONISHA PATEL, Jamie Rossjohn, ADAM ULDRICH, DALE GODFREY, Spencer Williams

American Chemical Society (ACS)

Abstract

Natural killer T cells express T cell receptors (TCRs) that recognize glycolipid antigens in association with the antigen-presenting molecule CD1d. Here, we report the concise chemical synthesis of a range of saturated and unsaturated α-glucosyl and α-glucuronosyl diacylglycerides of bacterial and fungal origins from allyl α-glucoside with Jacobsen kinetic resolution as a key step. We show that these glycolipids could be recognized by a classical type I NKT TCR that uses an invariant Vα14-Jα18 TCR α-chain, but also by an atypical NKT TCR that uses a different TCR α-chain (Vα10-Jα50). In both cases, recognition was sensitive to the lipid fine structure, and included recognition of glycosyl di..

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University of Melbourne Researchers

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