Document Detail


Elucidation of the Streptomyces coelicolor pathway to 2-undecylpyrrole, a key intermediate in undecylprodiginine and streptorubin B biosynthesis.
MedLine Citation:
PMID:  18291318     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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 an 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.
Authors:
SangJoon Mo; Paulina K Sydor; Christophe Corre; Mamoun M Alhamadsheh; Anna E Stanley; Stuart W Haynes; Lijiang Song; Kevin A Reynolds; Gregory L Challis
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemistry & biology     Volume:  15     ISSN:  1074-5521     ISO Abbreviation:  Chem. Biol.     Publication Date:  2008 Feb 
Date Detail:
Created Date:  2008-02-22     Completed Date:  2008-05-19     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9500160     Medline TA:  Chem Biol     Country:  England    
Other Details:
Languages:  eng     Pagination:  137-48     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Portland State University, Portland, OR 97207, USA.
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MeSH Terms
Descriptor/Qualifier:
Biosynthetic Pathways / genetics
Multigene Family / genetics
Prodigiosin / analogs & derivatives*,  biosynthesis,  chemistry
Pyrroles / metabolism*
Sequence Deletion
Streptomyces coelicolor / enzymology,  genetics*,  metabolism*
Grant Support
ID/Acronym/Agency:
BBSSK200310147//Biotechnology and Biological Sciences Research Council; GM077147/GM/NIGMS NIH HHS; GM50541/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/2-undecylpyrrole; 0/Pyrroles; 0/streptorubin B; 0/undecylprodiginine; 24311-00-0/prodiginine; 82-89-3/Prodigiosin

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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