期刊
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
卷 17, 期 10, 页码 1335-1341出版社
AMER CHEMICAL SOC
DOI: 10.1016/j.jasms.2006.05.019
关键词
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资金
- NCI NIH HHS [R01 CA96906] Funding Source: Medline
We examined the collisionally activated dissociation (CAD) pathways of protonated 2 '-deoxycytidine (dC), 5-formyl-2 '-deoxycytidine (5-FmdC), 5-hydroxy-2 '-deoxycytidine (5-OHdC), 5-hydroxymethyl-2 '-deoxycytidine (5-HmdC), and their corresponding stable isotope-labeled compounds to gain insights into the effects of modifications on the fragmentation pathways of the pyrimidine bases. Multi-stage MS (MS') results showed that protonated cytosine, its 5-hydroxyl-and 5-hydroxymethyl-substituted derivatives, but not its 5-formyl-substituted analog, could undergo Dimroth-like rearrangement in the gas-phase. The elimination of HNCO was one of the major fragmentation pathways observed for the protonated ions of all dC derivatives except for 5-hydroxymethylcytosine, which underwent this loss only after a H2O molecule had been eliminated. In addition, the protonated cytosine and 5-hydroxycytosine can undergo a facile elimination of NH3 molecule. This loss, however, was not observed for protonated 5-hydroxymethylcytosine, 5-formylcytosine, and their uracil analogs. Taken together, our study demonstrated that modifications could alter markedly the CAD patterns of the protonated pyrimidine bases. The results from this study provided a basis for the identifications of other modified pyrimidine bases/nucleosides by tandem mass spectrometry.
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