Document Detail

Bacterial formation and metabolism of 6-hydroxyhexanoate: evidence of a potential role for omega-oxidation.
MedLine Citation:
PMID:  6630146     Owner:  NLM     Status:  MEDLINE    
Alkane-utilizing strains of Pseudomonas spp. were found to omega-oxidize hexanoate, 6-hydroxyhexanoate, and 6-oxohexanoate to adipic acid in 5, 30, and 90% molar yields, respectively, after induction with n-hexane. 6-Hydroxyhexanoate was identified as the immediate product of hexanoate omega-hydroxylation by whole cells and was further oxidized into adipic acid and an unexpected metabolite identified as 2-tetrahydrofuranacetic acid. This same metabolite, together with adipic acid, was also detected when similarly induced cells were incubated with hexanoate or 1,6-hexanediol, but not with 6-oxohexanoate (adipic semialdehyde). Cells grown on hexanoate and incubated with 6-hydroxyhexanoate were also found to accumulate 2-tetrahydrofuranacetic acid, which was not further degraded. Utilization of 6-hydroxyhexanoate for growth was restricted to those organisms also able to utilize adipate. Similar observations were made with 1,6-hexanediol serving as the carbon source and cells obtained from one organism, Pseudomonas aeruginosa PAO, grown either on 1,6-hexanediol or 6-hydroxyhexanoate, were found to be well induced for both 6-oxohexanoate and adipate oxidation. The results indicate that 6-hydroxyhexanoate and 1,6-hexanediol are susceptible to both beta- and omega-oxidative attack; however, the former pathway appears to be of no physiological significance since it generates 2-tetrahydrofuranacetic acid as a nonmetabolizable intermediate, making omega-oxidation via adipate the exclusive pathway for degradation.
D A Kunz; P J Weimer
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of bacteriology     Volume:  156     ISSN:  0021-9193     ISO Abbreviation:  J. Bacteriol.     Publication Date:  1983 Nov 
Date Detail:
Created Date:  1983-12-17     Completed Date:  1983-12-17     Revised Date:  2010-09-10    
Medline Journal Info:
Nlm Unique ID:  2985120R     Medline TA:  J Bacteriol     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  567-75     Citation Subset:  IM    
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MeSH Terms
Caproates / metabolism*
Chromatography, Gas
Hexanoic Acids / metabolism*
Mass Spectrometry
Pseudomonas / genetics,  metabolism*
Species Specificity
Reg. No./Substance:
0/Caproates; 0/Hexanoic Acids; 1191-25-9/6-hydroxyhexanoic acid

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

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