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Total synthesis and biological evaluation of transvalencin Z.

ABSTRACT: The emerging global epidemic of drug-resistant tuberculosis has created an urgent need to identify novel therapeutic approaches for disease treatment. Transvalencin Z (1) is a natural product from Nocardia transvalensis with relatively potent and selective antimycobacterial activity against Mycobacterium smegmatis, making it an attractive target for structure-activity and mechanism of action studies. The total synthesis of the four possible diastereomers of transvalencin Z was completed (1a-d), and the absolute configurations were defined using chemical synthesis, HPLC retention times, and optical rotation measurements. Surprisingly, none of the transvalencin Z diastereomers exhibited any inhibitory activity against a panel of microbial pathogens, including several species of mycobacteria.

SUBMITTER: Nelson KM

PROVIDER: S-EPMC3381897 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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Total synthesis and biological evaluation of transvalencin Z.

Nelson Kathryn M KM Salomon Christine E CE Aldrich Courtney C CC

Journal of natural products 20120522 6

The emerging global epidemic of drug-resistant tuberculosis has created an urgent need to identify novel therapeutic approaches for disease treatment. Transvalencin Z (1) is a natural product from Nocardia transvalensis with relatively potent and selective antimycobacterial activity against Mycobacterium smegmatis, making it an attractive target for structure-activity and mechanism of action studies. The total synthesis of the four possible diastereomers of transvalencin Z was completed (1a-d), ...[more]

PMID: 22616579

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