Document Detail

Glucosamine-derived phospholipids in Escherichia coli. Structure and chemical modification of a triacyl glucosamine 1-phosphate found in a phosphatidylglycerol-deficient mutant.
MedLine Citation:
PMID:  6358219     Owner:  NLM     Status:  MEDLINE    
Certain Escherichia coli mutants defective in phosphatidylglycerol biosynthesis accumulate novel glucosamine-derived phospholipids. We previously demonstrated that the simplest of these substance (lipid X) is a diacylglucosamine 1-phosphate bearing beta-hydroxymyristoyl groups at positions 2 and 3 (Takayama, K., Qureshi, N., Mascagni, P., Nashed, M. A., Anderson, L., and Raetz, C. R. H. (1983) J. Biol. Chem. 258, 7379-7385). We now report the structural characterization of a triacylglucosamine 1-phosphate (designated lipid Y) that is also found in these mutants. Hydrolyzates of Y contain 2 mol of beta-hydroxymyristate and 1 mol of palmitate/mol of glucosamine. In the lipid, one of the beta-hydroxymyristates is amide-linked at position 2, while the two other fatty acyl groups are ester-linked. Fast atom bombardment mass spectrometry is used to confirm that Y is a monosaccharide derivative and that the molecular weight of Y as the free acid (C50H96NO13P) is 950.29. Analysis of Y by proton NMR spectroscopy at 200 MHz reveals that the anomeric configuration is alpha. Further, one of the esterified fatty acid residues is attached to the 3 OH of the sugar, while the second is linked to an OH moiety of a hydroxymyristate. The 4 and 6 OH groups of the sugar are unsubstituted, as in E. coli lipid X. To establish the precise location of each esterified fatty acyl residue, we subjected Y to a very mild alkaline hydrolysis in the presence of triethylamine. This resulted in the selective removal of a single hydroxymyristoyl group. The triethylamine-treated derivative (lipid Y) has a molecular weight of 723. NMR spectroscopy of Y shows that the 3 OH of the sugar is no longer substituted, while the beta OH of the remaining amide-linked hydroxymyristate is still esterified with palmitate. On the basis of these findings, we propose that lipid Y has the same fundamental structure as lipid X, except for the additional presence of a palmitoyl moiety on the N-linked hydroxymyristate. Presumably, lipid Y is synthesized from X by a selective acylation reaction.
K Takayama; N Qureshi; P Mascagni; L Anderson; C R Raetz
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  258     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  1983 Dec 
Date Detail:
Created Date:  1984-01-27     Completed Date:  1984-01-27     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  2985121R     Medline TA:  J Biol Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  14245-52     Citation Subset:  IM    
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MeSH Terms
Endotoxins / analysis
Escherichia coli / analysis*,  genetics
Glucosephosphates / analysis*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Weight
Phosphatidylglycerols / biosynthesis*
Grant Support
Reg. No./Substance:
0/Endotoxins; 0/Glucosephosphates; 0/Phosphatidylglycerols

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

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