Document Detail

Metabolites of a blocked chloramphenicol producer.
MedLine Citation:
PMID:  12542347     Owner:  NLM     Status:  MEDLINE    
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.
Elizabeth A Lewis; Tamara L Adamek; Leo C Vining; Robert L White
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of natural products     Volume:  66     ISSN:  0163-3864     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2003 Jan 
Date Detail:
Created Date:  2003-01-24     Completed Date:  2003-06-20     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  62-6     Citation Subset:  IM    
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3 Canada.
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MeSH Terms
4-Aminobenzoic Acid / 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*
Reg. No./Substance:
0/Anti-Bacterial Agents; 150-13-0/4-Aminobenzoic Acid; 2410-24-4/4-aminophenylalanine; 56-75-7/Chloramphenicol; 63-91-2/Phenylalanine

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