Review: Derivatization in mass spectrometry - 5. Specific derivatization of monofunctional compounds

Eur. J. Mass Spectrom. 11, 127–160 (2005)
DOI: 10.1255/ejms.712

Review: Derivatization in mass spectrometry – 5. Specific derivatization of monofunctional compounds

John M. Halket
Drug Control Centre, King’s College London, Franklin-Wilkins Building, Stamford Street, London SE1 9NH, UK. E-mail: john.halket@kcl.ac.uk
Vladimir G. Zaikin
Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Leninsky pr. 29, 119991 Moscow, Russia. E-mail: zaikin@ips.ac.ru

ABSTRACT:

The present paper is complementary to the foregoing reviews and describes some additional methods of the derivatization of particular functional groups mainly to enhance the structural information content of electron ionization and chemical ionization mass spectra. Derivatization approaches for the modification of unsaturated compounds, alcoholic, carboxylic, carbonyl, amine and other functional groups, are discussed. Derivatization for separation and quantitative determination of chiral enantiomeric compounds is also considered. Preliminary chemical and physical–chemical degradation for structure elucidation of high molecular weight compounds (biopolymers, synthetic polymers) is mentioned. Chemical aspects of derivatizations and characteristic mass spectral features of derivatives are described briefly. Some particular applications of chemical modification, in conjunction with mass spectral measurements for the analysis of various important bioorganic compounds and compounds in biological fluids, air, environmental etc., are considered.

Keywords: acetals, amines, 2-alkenyl-4,4-dimethyloxazoline derivatives, alkoholysis, O-alkyloximes, aminolysis, ammonolysis, benzylamines, O-benzyloximes, carbonyl compounds, carboxylic acids, chemical warfare agents, chiral separation, cyclic ethyleneketals, cyclic ethylenethioketals, cyclopropane compounds, cyclpropane-containing fatty acids, dimethyl disulphide addition, DMOX derivatives, enantiomers, epoxidation, GC/MS, hydrolysis, hydrolytic methylation, hydroxylamines, hydroxylation, hydrazones, imidazoline derivatives, inner salts, ketals, methoxy-mercuration reactions, nitriles, organotin compounds, oximes, oxirane-containing fatty acids, ozonolysis, quaternary amine salts, polyamides, polyesters, polymers, pyrolysis, pyrolysis-MS, pyrolysis-GC/MS, pyrrolidides, Schiff’s bases, O-substituted hydroxylamines, O-substituted oximes, O-silyl oximes, thiazolidinone derivatives, unsaturated compounds

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