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Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I.

Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I. Research Abstract Details 

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  • Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I. Abstract Text:

    clifton d leighClifton D Leigh,carolyn r bertozziCarolyn R Bertozzi,clifton d leighClifton D Leigh,carolyn r bertozziCarolyn R Bertozzi,

    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.

    Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I. Publishing Authors By Initials

    cd leighCD Leigh,cr bertozziCR Bertozzi,cd leighCD Leigh,cr bertozziCR Bertozzi,

    For similar abstracts research abstracts see: abstracts research

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    Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I. Journal Published:

    PUBLICATION TYPE: Journal Article

    Journal: The Journal of organic chemistry

    VOLUME: 73

    Page Numbers: 1008-17

    Journal Abbreviation: J. Org. Chem.

    ISSN: 0022-3263

    DAY: 4

    MONTH: 01

    YEAR: 2008

    Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I. Information

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    LANGUAGE: eng

    NlmUniqueID: 2985193

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    Grant and Affiliation Information for Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I.

    AFFILIATION: Departments of Chemistry and Molecular and Cell Biology and Howard Hughes Medical Institute, University of California, and Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, California 94720.

    Country: United States

    United States Research PublicationUnited States Research Publication

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    MEDLINETA: J Org Chem

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