Document Detail

A 13C NMR study of methyl-branched hydrocarbon biosynthesis in the housefly.
MedLine Citation:
PMID:  7118886     Owner:  NLM     Status:  MEDLINE    
Carbon 13 NMR, radiotracer and mass spectrometry studies were performed to confirm that propionate and methylmalonate are incorporated into long chain branched hydrocarbons as the methyl branch unit, to determine whether the branching methyl group was added initially or toward the end of the elongation process, to determine the precursor of methylmalonate, and to examine the metabolism of propionate in the housefly, Musca domestica. The labeled carbons from [3-13C]propionate and [methyl-13C]methylmalonate were incorporated into the branching methyl carbon of the methylalkanes, and into the even numbered carbons in alkanes and alkenes. The labeled carbons from [2-13C]propionate and [1-13C]propionate labeled the tertiary carbon and the carbon adjacent to the teritary carbon, respectively, in the methylalkanes. Mass spectral analysis of the methylalkanes after enrichment from [1-13C]propionate showed that propionate was incorporated during the initial stages of chain synthesis of the terminally branched alkanes. Sodium [2-13C]propionate labeled the odd numbered carbons of both the alkanes and alkenes. These data suggest that propionate is converted to an acetyl derivative, with carbon 3 of propionate converted to the carboxyl carbon of acetate, and carbon 2 of propionate converted to the methyl carbon of acetate. This pathway of propionate metabolism has hitherto only been reported in plants. The labeled carbons from DL-[3,4,5-13C3]valine were incorporated intact (as determined by 13C--13C coupling) into the branching methyl carbon, tertiary carbon, and carbon adjacent to the tertiary carbon, respectively, demonstrating that valine serves as a precursor to the methylmalonate used in branched alkane biosynthesis.
J W Dillwith; J H Nelson; J G Pomonis; D R Nelson; G J Blomquist
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  257     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  1982 Oct 
Date Detail:
Created Date:  1982-12-02     Completed Date:  1982-12-02     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985121R     Medline TA:  J Biol Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  11305-14     Citation Subset:  IM    
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MeSH Terms
Alkanes / metabolism*
Carbon Isotopes / diagnostic use
Houseflies / metabolism*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Structure-Activity Relationship
Reg. No./Substance:
0/Alkanes; 0/Carbon Isotopes

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

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