Mass spectral characterization of acyloxymethyl phosphates.
A series of organophosphates having one or two acyloxymethyl groups have been characterized by methane chemical ionization mass spectrometry: twelve are model compounds with phenyl and benzyl groups while four are derived from pyrimidine-3'-deoxyriboside-5'-monophosphates. Some are protonated cyclohexyl-ammonium salts. In addition the phenyl and benzyl phosphate spectra exhibit an abundance of fragmentation and rearrangement ions, the majority of which were products of three processes--expulsion of formaldehyde, loss of the acyloxymethyl group with transfer of hydrogen to the phosphate, and fission of the methylene-acyloxy bond. The pyrimidine-3'-deoxyriboside-5'-monophosphate esters give less fragmentation under similar circumstances; prominent ions in their spectra are the protonated molecular ions and losses of one and two molecules of formaldehyde from them and the protonated bases.
College of Pharmacy, Florida A&M University, Tallahassee 32307.
D N
DN
Srivastva
A
A
Srivastva
R G
RG
Smith
D001709:Biotechnology; D008401:Gas Chromatography-Mass Spectrometry; D007477:Ions; D015394:Molecular Structure; D008970:Molecular Weight; D009943:Organophosphorus Compounds
D007477:Ions; D009943:Organophosphorus Compounds