Mo, SangJoon, Sydor, Paulina K., Corre, Christophe, Alhamadsheh, Mamoun M., Stanley, Anna E., Haynes, Stuart W., Song, Lijiang, Reynolds, Kevin A. and Challis, Gregory L.. (2008) Elucidation of the Streptomyces coelicolor pathway to 2-undecylpyrrole, a key intermediate in undecylprodiginine and streptorubin B biosynthesis. Chemistry & Biology, Vol.15 (No.2). pp. 137-148. ISSN 1074-5521

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Abstract

The red gene cluster of Streptomyces coelicolor directs production of undecylprodiginine. Here we report that this gene cluster also directs production of streptorubin B and show that 2-undecylpyrrole (UP) is an intermediate in the biosynthesis of undecylprodiginine and streptorubin B. The redPQRKL genes are involved in UP biosynthesis. RedL and RedK are proposed to generate UP from dodecanoic acid or a derivative. A redK(-) mutant produces a hydroxylated undecylprodiginine derivative, whereas redL(-) and redK(-) mutants require addition of chemically synthesized UP for production of undecylprodiginine and streptorubin B. Fatty acid biosynthetic enzymes can provide dodecanoic acid, but efficient and selective prodiginine biosynthesis requires RedPQR Deletion of redP, redQ, or redR leads to an 80%-95% decrease in production of undecylprodiginine and and array of prodiginine analogs with varying alkyl chains. In a redR(-) mutant, the ratio of these can be altered in a logical manner by feeding various fatty acids.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry Q Science > QR Microbiology
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Streptomyces coelicolor, Biosynthesis, Antibiotics, Antibiotic-producing organisms
Journal or Publication Title:	Chemistry & Biology
Publisher:	Cell Press
ISSN:	1074-5521
Date:	February 2008
Volume:	Vol.15
Number:	No.2
Number of Pages:	12
Page Range:	pp. 137-148
Identification Number:	10.1016/j.chembiol.2007.11.015
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC), National Institutes of Health (U.S.) (NIH), European Union (EU), University of Warwick
Grant number:	GM50541 (NIH), GM077147 (NIH), 005224 (EU), BBSSK200310147 (BBSRC)
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URI:	http://wrap.warwick.ac.uk/id/eprint/30476

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