Versatile approach towards fully desymmetrized trehalose with a novel set of orthogonal protecting groups.

ABSTRACT: Trehalose-containing glycans play an essential role in bacterial pathogenesis, host-pathogen interaction, and cell signaling. The investigation of trehalose uptake and metabolism in Mycobacteria using synthetic desymmetrized trehalose probes is an important approach for the development of diagnostic tools and potential therapeutics for tuberculosis. Trehalose-derived mycobacterial glycolipids activate the innate immune response through recognition by the C-type lectin Mincle, justifying efforts to develop novel trehalose-based Mincle-dependent adjuvants. The chemical synthesis of trehalose-based glycoconjugates, glycolipids, and small-molecule trehalose probes requires the challenging chemical desymmetrization of eight hydroxyl groups in a C ₂-symmetric disa

SUBMITTER: Vasicek T 

PROVIDER: S-EPMC10808579 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature