Document Detail


Lipid A precursor from Pseudomonas aeruginosa is completely acylated prior to addition of 3-deoxy-D-manno-octulosonate.
MedLine Citation:
PMID:  2833499     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Inhibition of lipopolysaccharide (LPS) synthesis in Pseudomonas aeruginosa at the stage of incorporation of 3-deoxy-D-manno-octulosonate (KDO) caused accumulation of a lipid A precursor which contained all of the fatty acids present on the lipid A of mature LPS. The enzyme CTP:CMP-3-deoxy-D-manno-octulosonate cytidylyltransferase (CMP-KDO synthetase) from P. aeruginosa is inhibited by the KDO analog alpha-C-[1,5-anhydro-8-amino-2,7,8-trideoxy-D-manno-octopyranosyl] carboxylate (I), and I is effectively delivered to P. aeruginosa following attachment by amide linkage to the carboxyl terminus of alanylalanine. Intracellular hydrolysis releases the free inhibitor (I) which then inhibits activation of KDO by CMP-KDO synthetase causing accumulation of lipid A precursor and subsequent growth stasis. The major lipid A precursor species accumulated was purified and found to contain glucosamine, phosphate, C12:O, 2OH-C12:O and 3OH-C10:0 (in ester linkage), and 3OH-C12:0 (in amide linkage) in molar ratios of 1:1:0.5:0.5:1:1. Analysis of precursor by fast atom bombardment mass spectroscopy yielded a major ion (M - H)- of mass 1616 and fragments which were consistent with the structure of lipid A from P. aeruginosa. In contrast, Salmonella typhimurium, Escherichia coli, Citrobacter sp., Serratia marcescens, Enterobacter aerogenes, and Enterobacter cloacae all accumulated underacylated lipid A precursors which only contained 3-OH-C14:0, glucosamine, and phosphate. This difference and species-specific patterns of major and minor precursor species show that early steps in the assembly of lipid A are similar, but not identical in enteric and nonenteric Gram-negative bacteria.
Authors:
R C Goldman; C C Doran; S K Kadam; J O Capobianco
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Publication Detail:
Type:  Comparative Study; Journal Article    
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  263     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  1988 Apr 
Date Detail:
Created Date:  1988-05-23     Completed Date:  1988-05-23     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:  5217-23     Citation Subset:  IM    
Affiliation:
Anti-infective Research Division, Abbott Laboratories, Abbott Park, Illinois 60064.
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MeSH Terms
Descriptor/Qualifier:
Acetylglucosamine / metabolism
Acylation
Chromatography, High Pressure Liquid
Gas Chromatography-Mass Spectrometry
Glycolipids / isolation & purification*,  metabolism
Gram-Negative Bacteria / metabolism
Lipid A / analogs & derivatives*,  isolation & purification,  metabolism
Lipopolysaccharides / biosynthesis
Nucleotidyltransferases / metabolism
Pseudomonas aeruginosa / analysis*
Species Specificity
Sugar Acids / metabolism*
Chemical
Reg. No./Substance:
0/Glycolipids; 0/Lipid A; 0/Lipopolysaccharides; 0/Sugar Acids; 0/lipid A precursors, bacterial; 1069-03-0/2-keto-3-deoxyoctonate; 7512-17-6/Acetylglucosamine; EC 2.7.7.-/Nucleotidyltransferases; EC 2.7.7.38/3-deoxy-manno-octulosonate cytidyltransferase

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


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