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

Ki Hyun Kim; Timothy R. Ramadhar; Christine Beemelmanns; Shugeng Cao; Michael Thomas-Poulsen; Cameron R. Currie; Jon Clardy

doi:10.1039/C4SC01136H

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

Ki Hyun Kim, Timothy R. Ramadhar, Christine Beemelmanns, Shugeng Cao, Michael Thomas-Poulsen, Cameron R. Currie, Jon Clardy

Ecology and Evolution

55 Citations (Scopus)

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.

Original language	English
Journal	Chemical Science
Volume	5
Pages (from-to)	4333-4338
Number of pages	6
ISSN	2041-6520
DOIs	https://doi.org/10.1039/C4SC01136H
Publication status	Published - 1 Nov 2014

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title = "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.",

author = "Kim, {Ki Hyun} and Ramadhar, {Timothy R.} and Christine Beemelmanns and Shugeng Cao and Michael Thomas-Poulsen and Currie, {Cameron R.} and Jon Clardy",

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language = "English",

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T1 - Natalamycin A, an ansamycin from a termite-associated Streptomyces sp.

AU - Kim, Ki Hyun

AU - Ramadhar, Timothy R.

AU - Beemelmanns, Christine

AU - Cao, Shugeng

AU - Thomas-Poulsen, Michael

AU - Currie, Cameron R.

AU - Clardy, Jon

PY - 2014/11/1

Y1 - 2014/11/1

N2 - 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.

AB - 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.

U2 - 10.1039/C4SC01136H

DO - 10.1039/C4SC01136H

M3 - Journal article

C2 - 25386334

SN - 2041-6520

VL - 5

SP - 4333

EP - 4338

JO - Chemical Science

JF - Chemical Science

ER -

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

Abstract

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