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Effects of functional groups of acrylic acid derivatives as derivatization reagents for thiol compounds on molecular ion responses in electrospray ionization‐mass spectrometry
Author(s) -
Matsuura Kenji,
Takashina Hideo
Publication year - 1998
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(199812)33:12<1199::aid-jms736>3.0.co;2-w
Subject(s) - chemistry , trifluoroacetic acid , electrospray ionization , derivatization , acetic acid , mass spectrometry , reagent , chromatography , ammonium acetate , organic chemistry , high performance liquid chromatography
In order to explore the sensitivity enhancement of derivatizationreagents for thiol compounds with respect to liquidchromatography‐mass spectrometry (LC‐MS)analysis, the electrospray ionization (ESI)‐MS oftiopronin (TP) derivatives (TP‐MA,TP‐IBA, TP‐AMD, TP‐DMAE, TP‐TFE,TP‐AA and TP‐AMDSA; Fig. 1) obtained from theMichael addition reaction using seven structurally diverse acrylicacid analogues was investigated. This study focused on the molecularion species of TP derivatives and those response characteristicsobserved in LC‐MS using four mobile phases that containedcommonly used modifiers (trifluoroacetic acid, acetic acid,ammonium acetate and ammonium hydroxide). It was found thatTP‐DMAE gave an intense [M+H] + ion in all the mobile phases in the positive ion mode and its responsewas the highest among all of the TP derivatives owing to the highproton affinity of a dimethylamino group. The other TP derivativesgave different molecular ion species and lower responses based on themobile phase used. The formation of a dominant[M‐H] ‐ ion of TP‐AMDSA wasobserved in all the mobile phases owing to the high acidity of asulfonic acid group in the negative ion mode. TP‐TFE also gavestrong ion responses because it contains a high electronegative groupin the negative ion mode. The ion intensities of most of the TPderivatives could be enhanced by the addition of acetic acid andammonium hydroxide to the mobile phase and suppressed by the additionof trifluoroacetic acid and ammonium acetate in both ionization modes.These differences based on the mobile phase modifiers used werestrongly related to the ESI spray current on the ES capillary. ©1998 John Wiley & Sons, Ltd.