Document Detail

Structural studies on the core oligosaccharide of Phenylobacterium immobile strain K2 lipopolysaccharide. Chemical synthesis of 3-hydroxy-5c-dodecenoic acid.
MedLine Citation:
PMID:  4026999     Owner:  NLM     Status:  MEDLINE    
The fatty acid composition of the bound lipids of 17 strains from Phenylobacterium immobile was investigated. Ester-linked 3-hydroxy-5c-dodecenoic acid was found to be the major substituent in the lipopolysaccharide. Therefore the occurrence of this unusual acid can be taken as a useful marker for the determination of P. immobile by simple fatty acid analysis. Lipid A backbone was found to consist of 2,3-diamino-2,3-dideoxy-D-glucose, which up to this time has only been detected in group I of purple nonsulfur bacteria and their non-phototrophic relatives. A convenient chemical synthesis for 3-hydroxy-5c-dodecenoic acid is described. The polysaccharide region of P. immobile strain K2 lipopolysaccharide was investigated. The methods used included gel filtration procedures, methylation analysis, periodate oxidation, Smith degradation, oxidation with chromium trioxide and enzymic degradations of the isolated oligosaccharide. We found that strain K2 has a rough-type lipopolysaccharide, devoid of an O-specific side chain. For the core oligosaccharide the following structure is proposed: (Formula: see text) beta-D-Glcp(1-3)-L-alpha-D-Hep rho(1-3)-L-alpha-D-Hep rho(1-3-L-alpha-D-Hep rho(1-4/5)dOclA.
W Bellmann; F Lingens
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biological chemistry Hoppe-Seyler     Volume:  366     ISSN:  0177-3593     ISO Abbreviation:  Biol. Chem. Hoppe-Seyler     Publication Date:  1985 Jun 
Date Detail:
Created Date:  1985-10-08     Completed Date:  1985-10-08     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  8503054     Medline TA:  Biol Chem Hoppe Seyler     Country:  GERMANY, WEST    
Other Details:
Languages:  eng     Pagination:  567-75     Citation Subset:  IM    
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MeSH Terms
Carbohydrate Conformation
Chemical Phenomena
Chromatography, Gel
Fatty Acids / analysis
Gram-Negative Bacteria / analysis*
Lauric Acids / analysis*,  chemical synthesis
Lipid A / analysis
Lipids / analysis
Lipopolysaccharides / analysis*
Molecular Weight
Oligosaccharides / analysis*
Reg. No./Substance:
0/Fatty Acids; 0/Lauric Acids; 0/Lipid A; 0/Lipids; 0/Lipopolysaccharides; 0/Oligosaccharides; 1883-13-2/3-hydroxydodecanoic acid

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