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Natalamycin A, an Ansamycin from a Termite-Associated Streptomyces sp.

ABSTRACT: We report a preliminary functional and complete structural characterization of a highly unusual geldanamycin analog, natalamycin A, that was isolated from Streptomyces strain M56 recovered from a South African nest of Macrotermes natalensis termites. Bioassay-guided fractionation based on antifungal activity led to the isolation of natalamycin A, and a combination of NMR spectroscopy and X-ray crystallographic analysis, including highly-accurate quantum-chemical NMR calculations on the largest and most conformationally-flexible system to date, revealed natalamycin A's three-dimensional solid- and solution-state structure. This structure along with the structures of related compounds isolated from the same source suggest a geldanamycin-like biosynthetic pathway with unusual post-PKS modifications.

SUBMITTER: Kim KH

PROVIDER: S-EPMC4224317 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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Natalamycin A, an Ansamycin from a Termite-Associated Streptomyces sp.

Kim Ki Hyun KH Ramadhar Timothy R TR Beemelmanns Christine C Cao Shugeng S Poulsen Michael M Currie Cameron R CR Clardy Jon J

Chemical science 20141101 11

We report a preliminary functional and complete structural characterization of a highly unusual geldanamycin analog, natalamycin A, that was isolated from Streptomyces strain M56 recovered from a South African nest of Macrotermes natalensis termites. Bioassay-guided fractionation based on antifungal activity led to the isolation of natalamycin A, and a combination of NMR spectroscopy and X-ray crystallographic analysis, including highly-accurate quantum-chemical NMR calculations on ...[more]

PMID: 25386334

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