Document Detail

Compound-specific nitrogen isotope analysis of D-alanine, L-alanine, and valine: application of diastereomer separation to delta15N and microbial peptidoglycan studies.
MedLine Citation:
PMID:  19061396     Owner:  NLM     Status:  MEDLINE    
We have developed an analytical method to determine the compound-specific nitrogen isotope compositions of individual amino acid enantiomers using gas chromatography/combustion/isotope ratio mass spectrometry. A novel derivatization of amino acid diastereomers by optically active (R)-(-)-2-butanol or (S)-(+)-2-butanol offers two advantages for nitrogen isotope analysis. First, chromatographic chiral separation can be achieved without the use of chiral stationary-phase columns. Second, the elution order of these compounds on the chromatogram can be switched by a designated esterification reaction. We applied the method to the compound-specific nitrogen isotope analysis of D- and L-alanine in a peptidoglycan derived from the cell walls of cultured bacteria (Firmicutes and Actinobacteria; Enterococcus faecalis, Staphylococcus aureus, Staphylococcus staphylolyticus, Lactobacillus acidophilus, Bacillus subtilis, Micrococcus luteus, and Streptomyces sp.), natural whole bacterial cells (Bacillus subtilis var. natto), (pseudo)-peptidoglycan from archaea (Methanobacterium sp.), and cell wall from eukaryota (Saccharomyces cerevisiae). We observed statistically significant differences in nitrogen isotopic compositions; e.g., delta15N ( per thousand vs air) in Staphylococcus staphylolyticus for d-alanine (19.2 +/- 0.5 per thousand, n = 4) and L-alanine (21.3 +/- 0.8 per thousand, n = 4) and in Bacillus subtilis for D-alanine (6.2 +/- 0.2 per thousand, n = 3) and L-alanine (8.2 +/- 0.4 per thousand, n = 3). These results suggest that enzymatic reaction pathways, including the alanine racemase reaction, produce a nitrogen isotopic difference in amino acid enantiomers, resulting in 15N-depleted D-alanine. This method is expected to facilitate compound-specific nitrogen isotope studies of amino acid stereoisomers.
Yoshinori Takano; Yoshito Chikaraishi; Nanako O Ogawa; Hiroshi Kitazato; Naohiko Ohkouchi
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Analytical chemistry     Volume:  81     ISSN:  1520-6882     ISO Abbreviation:  Anal. Chem.     Publication Date:  2009 Jan 
Date Detail:
Created Date:  2009-01-01     Completed Date:  2009-02-09     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0370536     Medline TA:  Anal Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  394-9     Citation Subset:  IM    
Institute for Research on Earth Evolution (IFREE), Japan Agency for Marine-Earth Science and Technology (JAMSTEC), 2-15 Natsushima-cho, Yokosuka 237-0061, Japan.
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MeSH Terms
Alanine / analysis,  isolation & purification*
Bacteria / chemistry
Chromatography, Ion Exchange / methods
Gas Chromatography-Mass Spectrometry / methods*
Nitrogen Isotopes / analysis*
Peptidoglycan / analysis*
Valine / analysis,  isolation & purification*
Reg. No./Substance:
0/Nitrogen Isotopes; 0/Peptidoglycan; 56-41-7/Alanine; 7004-03-7/Valine

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

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