title: Use of S-pentafluorophenyl tris(2,4,6-trimethoxyphenyl)phosphonium acetate bromide and (4-hydrazino-4-oxobutyl) [tris(2,4,6-trimethoxyphenyl)phosphonium bromide for the derivatization of alcohols, aldehydes and ketones for detection by liquid chromatography/electrospray mass spectrometry.
abstract: The synthesis of S-pentafluorophenyl tris(2,4,6-trimethoxyphenyl)phosphonium acetate bromide (TMPP-AcPFP) and the novel compound (4-hydrazino-4-oxobutyl) [tris(2,4,6-trimethoxyphenyl)phosphonium bromide (TMPP-PrG) is described and the use of these compounds as derivatizing reagents for alcohols, aldehydes and ketones evaluated. Methods have been developed for the pre-column derivatization of alcohols using TMPP-AcPFP and for aldehydes and ketones using TMPP-PrG. The reactions were investigated by the use of a variety of individual test compounds containing the target functional groups. The TMPP acetyl ester and TMPP propyl hydrazone derivatives formed with their respective target analytes produced an enhanced response in electrospray ionization mass spectrometry (ESI-MS), and reproducible chromatography. The use of these two reagents to derivatize and facilitate detection of alcohols (including sugars and steroids), aldehydes and ketones (including steroids) by LC/ESI-MS was investigated.
authors.affiliation: Chemical Development, GlaxoSmithKline Research and Development Ltd., New Frontiers Science Park North, Harlow, UK.
authors.forename: Samantha J
authors.initials: SJ
authors.lastname: Barry
authors.forename: Richard M
authors.initials: RM
authors.lastname: Carr
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Lane
authors.forename: William J
authors.initials: WJ
authors.lastname: Leavens
authors.forename: Calvin O
authors.initials: CO
authors.lastname: Manning
authors.forename: Soraya
authors.initials: S
authors.lastname: Monté
authors.forename: Ian
authors.initials: I
authors.lastname: Waterhouse
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D002853:Chromatography, Liquid / Q000379:methods*; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
chemical_list: D000438:Alcohols; D000447:Aldehydes; D001965:Bromides; D007202:Indicators and Reagents; D007659:Ketones; D009943:Organophosphorus Compounds; C405845:tris(trimethoxyphenyl)phosphonium acetyl