Document Detail


Total synthesis of the novel bacterial fatty acid 16-methyl-8(Z)-heptadecenoic acid.
MedLine Citation:
PMID:  11687224     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The recently discovered bacterial fatty acid 16-methyl-8(Z)-heptadecenoic acid was synthesized for the first time in four steps (22% overall yield) starting from commercially available 8-methylnonanoic acid. The synthetic approach provided enough material to corroborate the structure and stereochemistry of the acid, which was recently identified in a Micrococcus bacterium from Lake Pomorie in Bulgaria. Reference equivalent-chain length values in nonpolar capillary gas chromatography for methyl 16-methyl-8(Z)-heptadecenoate and methyl 16-methyl-8(E)-heptadecenoate are also reported. This information will be helpful in subsequent characterizations of these fatty acids, as well as in the total identification of the fatty acid profile of bacteria producing these compounds.
Authors:
N M Carballeira; M Pagán
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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.; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  113     ISSN:  0009-3084     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  2001 Nov 
Date Detail:
Created Date:  2001-11-05     Completed Date:  2002-02-26     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  Ireland    
Other Details:
Languages:  eng     Pagination:  23-7     Citation Subset:  IM    
Affiliation:
Department of Chemistry, University of Puerto Rico, P.O. Box 23346, San Juan 00931-3346, Puerto Rico. ncarball@upracd.upr.clu.edu
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MeSH Terms
Descriptor/Qualifier:
Dioxolanes / chemical synthesis*,  chemistry
Fatty Acids, Monounsaturated / chemical synthesis*,  chemistry
Gas Chromatography-Mass Spectrometry
Micrococcus / chemistry*
Stereoisomerism
Grant Support
ID/Acronym/Agency:
SO6 GM 08102/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/4-(hydroxymethyl)-2-pentadecyl-1,3-dioxolane; 0/Dioxolanes; 0/Fatty Acids, Monounsaturated

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


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