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Chaxamycins A-D, Bioactive Ansamycins from a Hyper-arid Desert Streptomyces sp.

Lookup NU author(s): Chinyere Okoro, Professor Alan Bull, Professor Michael Goodfellow

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Abstract

Streptomyces sp. strain C34, isolated from soil collected in the Chilean hyper-arid Atacama Desert, was cultured on different media, resulting in the isolation and identification of four new ansamycin-type polyketides. The organism was selected for chemical investigation on the basis of a genome-mining PCR-based experiment targeting the gene encoding rifamycin-specific 3-amino5-hydroxybenzoic acid synthetase (AHBA). The isolated compounds were structurally characterized using NMR and MS techniques and named chaxamycins A D (1-4). Compounds 1-4 were tested for their antibacterial activity against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 and for their ability to inhibit the intrinsic ATPase activity of the heat shock protein 90 (Hsp90). Chaxamycin D (4), which showed a selective antibacterial activity against S. aureus ATCC 25923, was tested further against a panel of MRSA clinical isolates. In a virtual screening experiment, chaxamycins A D (1-4) have also been docked into the ATP-binding pocket in the N-terminal domain of the Hsp90, and the observed interactions are discussed.

Publication metadata

Author(s): Rateb ME, Houssen WE, Arnold M, Abdelrahman MH, Deng H, Harrison WTA, Okoro CK, Asenjo JA, Andrews BA, Ferguson G, Bull AT, Goodfellow M, Ebel R, Jaspars M

Publication type: Article

Publication status: Published

Journal: Journal of Natural Products

Year: 2011

Volume: 74

Issue: 6

Pages: 1491-1499

Print publication date: 09/05/2011

ISSN (print): 0163-3864

ISSN (electronic): 1520-6025

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/np200320u

DOI: 10.1021/np200320u

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