Document Detail


N6-(1-carboxyethyl)lysine formation by Streptococcus lactis. Purification, synthesis, and stereochemical structure.
MedLine Citation:
PMID:  3123486     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
During growth in an arginine-deficient (chemically defined) medium, cells of Streptococcus lactis K1 formed significant amounts of a previously undetected ninhydrin-positive compound. This intracellular compound did not cochromatograph with any of a wide range of amino acids or amino acid analogs tested. However, by two-dimensional thin layer chromatography, the unknown compound migrated close to the recently discovered N5-(1-carboxyethyl)ornithine (Thompson, J., Curtis, M. A., and Miller, S. P. F. (1986) J. Bacteriol. 167, 522-529; Miller, S. P. F., and Thompson, J. (1987) J. Biol. Chem. 262, 16109-16115). The purified compound behaved as a neutral amino acid and eluted between valine and methionine in the amino acid analyzer. The results of 1H NMR spectroscopy suggested the presence of a lysine backbone and a coupled methyl-methine unit in the molecule, and 13C NMR showed that there were nine carbon atoms, of which two (C-1 and C-7) were carboxyl carbons. The simplest structure compatible with the physicochemical data was that of an alkylated derivative of lysine. The identity of this new amino acid, N6-(1-carboxyethyl)lysine, was confirmed by chemical synthesis. In vivo labeling experiments conducted using L[U-14C]lysine and [epsilon-15N]lysine showed that exogenous lysine served as the precursor of intracellular N6-(1-carboxyethyl)lysine and that the epsilon-amino N atom was conserved during biosynthesis of the lysine derivative. Of the two possible diastereomers (2S,8S or 2S,8R) of N6-(1-carboxyethyl)lysine, comparative 13C NMR spectroscopy established that the amino acid produced by S. lactis K1 was exclusively of the 2S,8S configuration.
Authors:
J Thompson; S P Miller
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of biological chemistry     Volume:  263     ISSN:  0021-9258     ISO Abbreviation:  J. Biol. Chem.     Publication Date:  1988 Feb 
Date Detail:
Created Date:  1988-03-07     Completed Date:  1988-03-07     Revised Date:  2000-12-18    
Medline Journal Info:
Nlm Unique ID:  2985121R     Medline TA:  J Biol Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  2064-9     Citation Subset:  IM    
Affiliation:
Microbiology Section, National Institute of Dental Research, Bethesda, Maryland 20892.
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MeSH Terms
Descriptor/Qualifier:
Amino Acids / analysis
Chromatography, Thin Layer
Lactococcus lactis / metabolism*
Lysine / analogs & derivatives*,  biosynthesis,  isolation & purification
Magnetic Resonance Spectroscopy
Stereoisomerism
Chemical
Reg. No./Substance:
0/Amino Acids; 56-87-1/Lysine; 5746-03-2/N(6)-(1-carboxyethyl)lysine

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


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