title: Analysis of amino acids by gas chromatography-flame ionization detection and gas chromatography-mass spectrometry: simultaneous derivatization of functional groups by an aqueous-phase chloroformate-mediated reaction.
abstract: The one-step ethyl chloroformate derivatization of amino acids in an aqueous medium is extended with the use of a variety of alkyl chloroformate reagents. This provides a new and convenient procedure for preparing esters with different alkoxy groups. A new mechanism for esterification during chloroformate derivatization is proposed based on the formation of an intermediate mixed carboxylic-carbonic acid anhydride followed by the exchange with an alcohol. Among the different reagents investigated, isobutyl chloroformate derivatized amino acids were found to provide more sensitivity for analyses by GC-flame ionization detection and GC-MS relative to derivatives prepared by other alkyl chloroformates.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing 48824.
authors.forename: J
authors.initials: J
authors.lastname: Wang
authors.forename: Z H
authors.initials: ZH
authors.lastname: Huang
authors.forename: D A
authors.initials: DA
authors.lastname: Gage
authors.forename: J T
authors.initials: JT
authors.lastname: Watson
mesh_terms: D000596:Amino Acids / Q000032:analysis*; D002849:Chromatography, Gas / Q000379:methods*; D005410:Flame Ionization; D005561:Formates; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D014867:Water
chemical_list: D000596:Amino Acids; D005561:Formates; D014867:Water; C083354:chlorocarbonic acid