Asymmetric Total Synthesis of Mycobacterial Diacyl Trehaloses Demonstrates a Role for Lipid Structure in Immunogenicity.

ABSTRACT: The first asymmetric total synthesis of three structures proposed for mycobacterial diacyl trehaloses, DAT₁, DAT₂, and DAT₃ is reported. The presence of two of these glycolipids, DAT₁ and DAT₃, within different strains of pathogenic M. tuberculosis was confirmed, and it was shown that their abundance varies significantly. In mass spectrometry, synthetic DAT₂ possessed almost identical fragmentation patterns to presumptive DAT₂ from Mycobacterium tuberculosis H37Rv, but did not coelute by HPLC, raising questions as the precise relationship of the synthetic and natural materials. The synthetic DATs were examined as agonists for signaling by the C-type lectin, Mincle. The small differences in the chemical stru

SUBMITTER: Holzheimer M 

PROVIDER: S-EPMC7372558 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature