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

ABSTRACT: DAT₂ is a member of the diacyl trehalose family (DAT) of antigenic glycolipids located in the mycomembrane of Mycobacterium tuberculosis (Mtb). Recently it was shown that the molecular structure of DAT₂ had been incorrectly assigned, but the correct structure remained elusive. Herein, the correct molecular structure of DAT₂ and its methyl-branched acyl substituent mycolipanolic acid is determined. For this, four different stereoisomers of mycolipanolic acid were prepared in a stereoselective and unified manner, and incorporated into DAT₂. A rigorous comparison of the four isomers to the DAT isolated from Mtb H37Rv by NMR, HPLC, GC, and mass spectrometry allowed a structural revision of mycolipanolic acid and DAT₂. Activation of the mac

SUBMITTER: Lin Z 

PROVIDER: S-EPMC11482735 | biostudies-literature | 2024 May

REPOSITORIES: biostudies-literature