Asymmetric Total Synthesis and Structural Revision of DAT2, an Antigenic Glycolipid from Mycobacterium tuberculosis

• DOI: 10.1002/ange.202318582
• Publication Date: 2024-03-08T09:09:37Z
• Authors: Zonghao Lin; Jeya Prathap Kaniraj; Mira Holzheimer; Jérôme Nigou; Martine Gilleron; Johan Hekelaar; Adriaan J. Minnaard
• Keywords: Antigenicity

Abstract DAT 2 is a member of the diacyl trehalose family (DAT) antigenic glycolipids located in mycomembrane Mycobacterium tuberculosis ( Mtb ). Recently it was shown that molecular structure had been incorrectly assigned, but correct remained elusive. Herein, and its methyl‐branched acyl substituent mycolipanolic acid determined. For this, four different stereoisomers were prepared stereoselective unified manner, incorporated into . A rigorous comparison isomers to isolated from H37Rv by NMR, HPLC, GC, mass spectrometry allowed structural revision Activation macrophage inducible Ca 2+ ‐dependent lectin receptor (Mincle) with all shows natural stereochemistry / provides strongest activation, which indicates high antigenicity potential application serodiagnostics vaccine adjuvants.