title: 4-(6-methoxy-2-naphthyl)-2-butyl chloroformate enantiomers: new reagents for the enantiospecific analysis of amino compounds in biogenic matrices.
abstract: (+)- and (-)-4-(6-methoxy-2-naphthyl)-2-butyl chloroformate (NAB-C) were prepared from the prochiral non-steroidal anti-inflammatory agent nabumetone with the aim of developing easily detectable chloroformate reagents for the enantiospecific HPLC analysis of amino compounds in biogenic matrices on achiral stationary phases. The new reagents were tested in the derivatization of beta-adrenoceptor antagonists and anti-arrhythmic agents and allowed derivatization in the presence of water. (+)- and (-)-NAB-C were compared with other reagents with a 6-methoxy-2-naphthyl moiety as a chromophore. The reagents were suitable for the analysis of nanogram amounts of, for example, metoprolol enantiomers in plasma, a prerequisite for application in pharmaco- or toxicokinetic studies.
authors.affiliation: Department of Pharmacology, Johann Wolfgang Goethe-University, Frankfurt am Main, Germany.
authors.forename: R
authors.initials: R
authors.lastname: Büschges
authors.forename: R
authors.initials: R
authors.lastname: Devant
authors.forename: E
authors.initials: E
authors.lastname: Mutschler
authors.forename: H
authors.initials: H
authors.lastname: Spahn-Langguth
mesh_terms: D000319:Adrenergic beta-Antagonists / Q000097:blood*; D000328:Adult; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D001679:Biogenic Amines / Q000032:analysis*; D002074:Butanones / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D006801:Humans; D007202:Indicators and Reagents; D008297:Male; D008790:Metoprolol / Q000097:blood*; D000077430:Nabumetone; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000319:Adrenergic beta-Antagonists; D000894:Anti-Inflammatory Agents, Non-Steroidal; D001679:Biogenic Amines; D002074:Butanones; D007202:Indicators and Reagents; D008790:Metoprolol; D000077430:Nabumetone