title: N-ethoxycarbonylation combined with (S)-1-phenylethylamidation for enantioseparation of amino acids by achiral gas chromatography and gas chromatography-mass spectrometry.
abstract: N-ethoxycarbonylation was combined with (S)-1-phenylethylamidation for enantioseparation of amino acids by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) on achiral capillary columns. The method provided complete enantioseparations of 12 amino acids as diastereomeric N-ethoxycarbonyl/(S)-1-phenylethylamides with exceptional resolutions for proline (R(s) > or = 9.9) and pipecolic acid (R(s) > or = 10.2). GC-MS analysis in selected ion monitoring mode employing standard addition method, facilitated quantitation of D-pipecolic acid in kidney bean (0.95 microg/10 mg) and adzuki bean (0.14 microg/10 mg). The peak area ratios indicated that they had the identical chiral composition at 2.5% for D-pipecolic acid and 97.5% for L-pipecolic acid.
authors.affiliation: Metabolomic Analysis Laboratory, Institute for Neuroregeneration and Stem Cell Research, School of Medicine, Ajou University, Suwon 443-721, South Korea.
authors.forename: Man-Jeong
authors.initials: MJ
authors.lastname: Paik
authors.forename: Jinwoo
authors.initials: J
authors.lastname: Lee
authors.forename: Kyoung-Rae
authors.initials: KR
authors.lastname: Kim
mesh_terms: D000596:Amino Acids / Q000032:analysis* / Q000737:chemistry; D002849:Chromatography, Gas / Q000379:methods*; D007887:Fabaceae / Q000737:chemistry; D005563:Formic Acid Esters / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D016018:Least-Squares Analysis; D027805:Phaseolus / Q000737:chemistry; D010627:Phenethylamines / Q000378:metabolism; D015203:Reproducibility of Results; D012680:Sensitivity and Specificity; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D005563:Formic Acid Esters; D010627:Phenethylamines; C007658:ethyl chloroformate