Document Detail


Para-position derivatives of fungal anthelmintic cyclodepsipeptides engineered with Streptomyces venezuelae antibiotic biosynthetic genes.
MedLine Citation:
PMID:  15184904     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
PF1022A, a cyclooctadepsipeptide possessing strong anthelmintic properties and produced by the filamentous fungus Rosellinia sp. PF1022, consists of four alternating residues of N-methyl-L-leucine and four residues of D-lactate or D-phenyllactate. PF1022A derivatives obtained through modification of their benzene ring at the para-position with nitro or amino groups act as valuable starting materials for the synthesis of compounds with improved anthelmintic activities. Here we describe the production of such derivatives by fermentation through metabolic engineering of the PF1022A biosynthetic pathway in Rosellinia sp. PF1022. Three genes cloned from Streptomyces venezuelae, and required for the biosynthesis of p-aminophenylpyruvate from chorismate in the chloramphenicol biosynthetic pathway, were expressed in a chorismate mutase-deficient strain derived from Rosellinia sp. PF1022. Liquid chromatography-mass spectrometry and NMR analyses confirmed that this approach facilitated the production of PF1022A derivatives specifically modified at the para-position. This fermentation method is environmentally safe and can be used for the industrial scale production of PF1022A derivatives.
Authors:
Koji Yanai; Naomi Sumida; Kaoru Okakura; Tatsuki Moriya; Manabu Watanabe; Takeshi Murakami
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Publication Detail:
Type:  Journal Article     Date:  2004-06-06
Journal Detail:
Title:  Nature biotechnology     Volume:  22     ISSN:  1087-0156     ISO Abbreviation:  Nat. Biotechnol.     Publication Date:  2004 Jul 
Date Detail:
Created Date:  2004-07-01     Completed Date:  2005-01-24     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9604648     Medline TA:  Nat Biotechnol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  848-55     Citation Subset:  IM    
Affiliation:
Microbiological Resources and Technology Laboratories, Meiji Seika Kaisha, Ltd., 788 Kayama, Odawara-shi, Kanagawa 250-0852, Japan. koji_yanai@meiji.co.jp
Data Bank Information
Bank Name/Acc. No.:
GENBANK/AB116234;  AB116235;  AB116236
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MeSH Terms
Descriptor/Qualifier:
Animals
Anthelmintics / chemistry*,  metabolism*
Base Sequence
Biotransformation
Chloramphenicol / biosynthesis*
Cloning, Molecular
Depsipeptides / biosynthesis,  chemistry*,  genetics,  metabolism*
Fermentation
Genetic Engineering
Molecular Sequence Data
Streptomyces / genetics*,  metabolism
Chemical
Reg. No./Substance:
0/Anthelmintics; 0/Depsipeptides; 133413-70-4/PF 1022A; 56-75-7/Chloramphenicol

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


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