Issue 11, 2014

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.

Graphical abstract: Natalamycin A, an ansamycin from a termite-associated Streptomyces sp.

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Apr 2014
Accepted
14 Jul 2014
First published
14 Jul 2014

Chem. Sci., 2014,5, 4333-4338

Natalamycin A, an ansamycin from a termite-associated Streptomyces sp.

K. H. Kim, T. R. Ramadhar, C. Beemelmanns, S. Cao, M. Poulsen, C. R. Currie and J. Clardy, Chem. Sci., 2014, 5, 4333 DOI: 10.1039/C4SC01136H

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