Characterization of novel nucleoside analogs by electrospray ionization mass spectra

Eur. J. Mass Spectrom. 10, 699–703 (2004)
DOI: 10.1255/ejms.678

Characterization of novel nucleoside analogs by electrospray ionization mass spectra

Liu Yan,^a Chen Xiao- Lan,^b He Juan,^c Hou Jian-Bo,^bQu Ling-Bo^a and Zhao Yu-Fen^a,b,d*
^aThe Key Laboratory for Chemical Biology of Fujian Province, Department of Chemistry, Xiamen University, Xiamen, 361005, PR China
^bDepartment of Chemistry, Zhengzhou University, Zhengzhou, 450052, PR China
^cDepartment of Chemistry, Zhengzhou Engineering Institute, Zhengzhou, 450052, PR China
^dThe Key Laboratory of Bioorganic Phosphorous Chemistry of Education Ministry, Department of Chemistry, School of Life Science and Engineering, Tsinghua University, Beijing 100084, PR China

ABSTRACT:

In this paper, we synthesized a novel nucleoside analog by coupling thymine with dimethyl dicarboxylate biphenyl (DDB). The structure of the target compound was determined using ¹H nuclear magnetic resonance (NMR) and electrospray ionization tandem mass spectrometry (ESI-MS/MS). The fragmentation pathways were studied in details through ESI-MS/MS. By comparing with unsubstituted nucleosides, such as AZT, MCI, d4T and DDI, it was found that the nucleoside analog coupled with DDB would not yield the daughter ions corresponding to the fragments of the nucleoside base and arabinofuranose analogs, but would lose a neutral molecule HF and DDB easily. However, the unsubstituted nucleosides could lightly yield the fragment ions of the nucleoside base and sugar ring. Hence, electrospray ionization mass spectrometry combined with tandem mass spectrometry (MS/MS) provides a convenient method to recognize the substituted and unsubstituted nucleosides.

Keywords: nucleoside analogue, dimethyl dicarboxylate biphenyl (DDB), ESI-MS/MS

You can buy this paper on-line in PDF format; it costs only £11.75. Just click on the BUY on-line button. You can pay on-line through a secure server and get access immediately.