| Metabolites of a blocked chloramphenicol producer. | |
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MedLine Citation:
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PMID: 12542347 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Addition of p-aminophenylalanine (4), an advanced biosynthetic precursor of the antibiotic chloramphenicol (5), to a Streptomyces venezuelae pabAB mutant (VS629) restored chloramphenicol production and led to formation of the non-chlorinated analogue corynecin II (6) and four acetanilide derivatives: p-(acetylamino)phenylalanine (7), p-(acetylamino)benzyl alcohol (13), p-(acetylamino)benzoic acid (14), and p-(acetylamino)phenol (acetaminophen, 16). Metabolite structures were deduced from NMR and MS-MS data and established by chromatographic and spectroscopic comparisons with authentic samples. Reference compound 13 was synthesized by reducing the acid chloride of 14. Shunt pathways are proposed to account for the formation of the metabolites from p-aminophenylalanine. |
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Authors:
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Elizabeth A Lewis; Tamara L Adamek; Leo C Vining; Robert L White |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of natural products Volume: 66 ISSN: 0163-3864 ISO Abbreviation: J. Nat. Prod. Publication Date: 2003 Jan |
Date Detail:
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Created Date: 2003-01-24 Completed Date: 2003-06-20 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 7906882 Medline TA: J Nat Prod Country: United States |
Other Details:
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Languages: eng Pagination: 62-6 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3 Canada. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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4-Aminobenzoic Acid
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metabolism Anti-Bacterial Agents / biosynthesis* Chloramphenicol / biosynthesis* Chromatography, High Pressure Liquid Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Structure Phenylalanine / analogs & derivatives*, pharmacology* Streptomyces / drug effects*, enzymology* |
| Chemical | |
Reg. No./Substance:
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0/Anti-Bacterial Agents; 150-13-0/4-Aminobenzoic Acid; 2410-24-4/4-aminophenylalanine; 56-75-7/Chloramphenicol; 63-91-2/Phenylalanine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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