Work

Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

Year: 2008

Type: article

Abstract: Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo702032c

Authors: Clifton D. Leigh, Carolyn R. Bertozzi

Institutions: Howard Hughes Medical Institute, Lawrence Berkeley National Laboratory, Molecular Foundry, University of California, Berkeley

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

SDG: Good health and well-being

Open Access status: green

Funders: Howard Hughes Medical Institute, National Institute of Allergy and Infectious Diseases