Abstract
Fragmentation reactions of protonated α-amino acids (AAs) were studied previously using tandem mass spectrometry (MS/MS) of unit mass resolution. Isobaric fragmentation products and minor fragmentation products could have been overlooked or misannotated. In the present study, we examined the fragmentation patterns of 19 AAs using high-resolution electrospray ionization MS/MS (HR-ESI-MS/MS) with collision-induced dissociation (CID). Isobaric fragmentation products from protonated Met and Trp were resolved and identified for the first time. Previously unreported fragmentation products from protonated Met, Cys, Gln, Arg, and Lys were observed. Additionally, the chemical identity of a fragmentation product from protonated Trp that was incorrectly annotated in previous investigations was corrected. All previously unreported fragmentation products and reactions were verified by pseudo MS3 experiments and/or MS/MS analyses of deuterated AAs. Clearer pictures of the fragmentation reactions for Met, Cys, Trp, Gln, Arg and Lys were obtained in the present study.
Highlights
Amino acid (AA) is a class of compounds present in every biological system
With respect to the mass range (i.e., m/z 50 to 6000) of our HR-ESI-MS/MS system, we studied the fragmentation patterns of 18 proteinogenic AAs, but not those of glycine (75 Da) and alanine (89 Da)
Using the HR-ESI-MS/MS with collision-induced dissociation (CID), previously incorrectly annotated fragment products and previously unreported fragment products from protonated AAs were identified in the present study
Summary
Amino acid (AA) is a class of compounds present in every biological system. AA analysis is of particular importance in health and food science. Investigation on fragmentation reactions of AAs helps to interpret fragmentation patterns of AA derivatives and peptides[8,9,10,11]. Fragmentation patterns of protonated AAs were examined using HR-ESI-MS/MS with collision-induced dissociation (CID). With respect to the mass range (i.e., m/z 50 to 6000) of our HR-ESI-MS/MS system, we studied the fragmentation patterns of 18 proteinogenic AAs, but not those of glycine (75 Da) and alanine (89 Da). Using the HR-ESI-MS/MS with CID, previously incorrectly annotated fragment products and previously unreported fragment products from protonated AAs were identified in the present study. Together pseudo MS3 experiments[19] and analyses of deuterated forms, fragmentation reactions of the protonated AAs were clearly elucidated
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