Derivatization for liquid chromatography/electrospray mass spectrometry: synthesis of tris(trimethoxyphenyl)phosphonium compounds and their derivatives of amine and carboxylic acids

William J Leavens; Stephen J Lane; Richard M Carr; Andrea M Lockie; Ian Waterhouse

doi:10.1002/rcm.559

Derivatization for liquid chromatography/electrospray mass spectrometry: synthesis of tris(trimethoxyphenyl)phosphonium compounds and their derivatives of amine and carboxylic acids

Rapid Commun Mass Spectrom. 2002;16(5):433-41. doi: 10.1002/rcm.559.

Authors

William J Leavens¹, Stephen J Lane, Richard M Carr, Andrea M Lockie, Ian Waterhouse

Affiliation

¹ Department of Metabolism and Pharmacokinetics, Glaxo Research and Development Ltd., Park Road, Ware, Hertfordshire SG12 0DP, UK. [email protected]

PMID: 11857728
DOI: 10.1002/rcm.559

Abstract

A simple method for the derivatization of primary amines and carboxylic acids with tris(trimethoxyphenyl)phosphonium (TMPP) reagents to enhance their detection by electrospray mass spectrometry (ESI-MS) has been developed. The synthesis of novel TMPP reagents and their stable isotopically labelled analogues is described. Through the use of stable isotopically labelled TMPP "tags", incorporation of a doublet (1:1, (1)H/(2)H or (12)C/(13)C) into the target molecule can be achieved, enabling the use of isotopic target analysis to detect compounds of unknown molecular weight but with a characteristic isotope pattern and accurate mass difference.