Analysis of alcohols, as dimethylglycine esters, by electrospray ionization tandem mass spectrometry.
Dimethylglycine (DMG) esters are new derivatives for the rapid, sensitive and selective analysis of primary and secondary alcohols, in complex mixtures, by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Their development was inspired by the use of the complementary dimethylaminoethyl esters for the trace, rapid analysis of fatty acids. DMG esters are simply prepared by heating a dichloromethane solution of the imidazolide of dimethylglycine, containing triethylamine, and an alcohol. DMG esters of long-chain fatty alcohols, isoprenoidal alcohols and hydroxy-acids are analysed by electrospray ionization tandem mass spectrometry with a precursor ion of m/z 104 scan. Diols, glyceryl esters, glyceryl ethers and some sterols are analysed by a neutral loss of 103 Da scan. Trimethylglycine (TMG) ester iodides, prepared by alkylation of DMG esters with methyl iodide, are more sensitive derivatives for molecules containing secondary alcohol groups, such as cholesterol and gibberellic acid. They are analysed by a precursor ion of m/z 118 scan. DMG or TMG derivatives were shown to be at least comparable and sometimes an order of magnitude more sensitive than N-methylpyridyl ether derivatives for ESI-MS/MS analysis of the different classes of alcohols. Applications of these derivatives for the diagnosis of inherited disorders and the analysis of natural products are presented.
Johnson
D W
DW
Department of Chemical Pathology, Women's and Children's Hospital, 72 King William Road, North Adelaide, South Australia 5006 Australia. david.johnson@adelaide.edu.au
D000438:Alcohols / Q000032:analysis* / Q000737:chemistry; D001622:Betaine / Q000032:analysis / Q000138:chemical synthesis; D004952:Esters / Q000032:analysis / Q000138:chemical synthesis; D007093:Imidazoles / Q000737:chemistry; D012521:Sarcosine / Q000031:analogs & derivatives / Q000032:analysis* / Q000138:chemical synthesis; D012680:Sensitivity and Specificity; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
D000438:Alcohols; D004952:Esters; D007093:Imidazoles; D001622:Betaine; C006900:N,N-carbonyldiimidazole; C025138:dimethylglycine; D012521:Sarcosine