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Title: Chemical derivatisation for LC-MS
Author: Leavens, W. J.
Awarding Body: University of Wales Swansea
Current Institution: Swansea University
Date of Award: 2003
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The investigation of the chemical derivatisation of low molecular weight compounds containing carboxylic acid, amine, alcohol, aldehyde or ketone functional groups by novel reagents designed to enhance their response by liquid chromatography-electrospray ionisation mass spectrometry (LC-ESI/MS) is described. A series of novel reagents containing functionalised ferrocene or tris(2,4,6-trimethoxyphenyl)phosphonium (TMPP) moieties were synthesised for pre-column derivatisation of the target analytes. The ferrocene reagents enabled facile electrospray ionisation, through formation of the molecular cation or the protonated molecular ion, whilst the TMPP reagents provided a molecular cation (or "pre-charged" species). Additionally, the ferrocene reagents provided an elemental tag to facilitate analysis of the derivative by inductively coupled plasma mass spectrometry (ICP/MS). Carboxylic acids were activated by chloromethylpyridinium iodide in the presence of an organic base or by a water-soluble carbodiimide and reacted with an amine to produce a stable amide linkage. Both carboxylic acid and amine-containing analogues of ferrocene and TMPP were synthesised for use with this coupling reaction. Derivatisation of aldehydes and ketones was achieved by reaction of hydrazino analogues of TMPP to form hydrazone derivatives. Additionally, derivatisation was also achieved through the use of activated esters of ferrocene and TMPP and their nucleophilic displacement reaction with amines.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available