title: The 'apparent' hydrolysis of alkyl esters during electrospray ionization.
abstract: Electrospray ionization (ESI) mass spectrometry was employed to obtain both molecular weight confirmation and structural information for a series of novel alkenyldiarylmethane (ADAM) analogs. The mass spectral data were intended for use during the structure elucidation of ester hydrolysis products formed during an in vitro metabolism study of a series of novel ADAM analogs. The data on the precursor molecules show the presence of the molecular ion peak, [M+H](+), as well as a peak consistent with the hydrolysis product of the original ester ([MH-ROH+H(2)O](+)). However, chemical ionization mass spectrometry, elemental analysis and (1)H NMR data indicated the presence of only the intact diester compounds, suggesting that the formation of the hydrolysis product was an instrumental artifact, i.e., in-beam hydrolysis during ESI or a result of longer ion residence times of the ion trap mass analyzer.
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN 47907, USA.
authors.forename: Maximilian A
authors.initials: MA
authors.lastname: Silvestri
authors.forename: Deborah
authors.initials: D
authors.lastname: Miles
authors.forename: Arlene P
authors.initials: AP
authors.lastname: Rothwell
authors.forename: Karl V
authors.initials: KV
authors.lastname: Wood
authors.forename: Mark
authors.initials: M
authors.lastname: Cushman
mesh_terms: D000478:Alkylation; D001577:Benzophenones / Q000032:analysis / Q000737:chemistry; D002208:Caproates / Q000032:analysis* / Q000737:chemistry; D004952:Esters / Q000032:analysis / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D006868:Hydrolysis; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D001577:Benzophenones; D002208:Caproates; D004952:Esters; C047723:benzophenone