| Para-position derivatives of fungal anthelmintic cyclodepsipeptides engineered with Streptomyces venezuelae antibiotic biosynthetic genes. | |
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MedLine Citation:
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PMID: 15184904 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Koji Yanai; Naomi Sumida; Kaoru Okakura; Tatsuki Moriya; Manabu Watanabe; Takeshi Murakami |
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Publication Detail:
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Type: Journal Article Date: 2004-06-06 |
Journal Detail:
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Title: Nature biotechnology Volume: 22 ISSN: 1087-0156 ISO Abbreviation: Nat. Biotechnol. Publication Date: 2004 Jul |
Date Detail:
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Created Date: 2004-07-01 Completed Date: 2005-01-24 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9604648 Medline TA: Nat Biotechnol Country: United States |
Other Details:
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Languages: eng Pagination: 848-55 Citation Subset: IM |
Affiliation:
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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.:
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GENBANK/AB116234; AB116235; AB116236 |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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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:
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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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