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Elucidation of the Streptomyces coelicolor pathway to 2-undecylpyrrole, a key intermediate in undecylprodiginine and streptorubin B biosynthesis
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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. doi:10.1016/j.chembiol.2007.11.015 ISSN 1074-5521.
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Official URL: http://dx.doi.org/10.1016/j.chembiol.2007.11.015
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 | ||||
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Subjects: | Q Science > QD Chemistry Q Science > QR Microbiology |
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Divisions: | Faculty of Science, Engineering and Medicine > 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 | ||||
Official Date: | February 2008 | ||||
Dates: |
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Volume: | Vol.15 | ||||
Number: | No.2 | ||||
Number of Pages: | 12 | ||||
Page Range: | pp. 137-148 | ||||
DOI: | 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) |
Data sourced from Thomson Reuters' Web of Knowledge
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