ESI-MS/MS for the differentiation of diastereomeric pyrimidine glycols in mononucleosides

Yinsheng Wang, Shetty Vivekananda, Kangling Zhang

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Pyrimidine glycols, or 5,6-dihydroxy-5,6-dihydropyrimidines, are primary lesions in DNA induced by reactive oxygen species. In this article, we report the preparation and tandem mass spectrometry (MS/MS) characterization of the two cis diastereomers of the glycol lesions of 2′-deoxyuridine, 5-methyl-2′-deoxycytidine, and thymidine. Our results show that collisional activation of the [M + Na]+ ions of all the three pairs of cis isomers and that of the [M + H]+ ions of the 2′-deoxyuridine glycols and 5-methyl-2′-deoxycytidine glycols give a facile loss of a water molecule. Interestingly, the water loss occurs more readily for the 6S isomer than for the 6R isomer. Likewise, product ion spectra of the [M - H]- ions of the two cis isomers of the 2′-deoxyuridine glycols and thymidine glycols show more facile loss of water for the 6S isomer than for the 6R isomer. MS/MS acquired at different collisional energies gave similar results, which establishes the reproducibility of spectra.

Original languageEnglish (US)
Pages (from-to)4505-4512
Number of pages8
JournalAnalytical Chemistry
Volume74
Issue number17
DOIs
StatePublished - Sep 1 2002
Externally publishedYes

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Glycols
Isomers
5-methyldeoxycytidine
Deoxyuridine
Ions
Water
Thymidine
Mass spectrometry
pyrimidine
Reactive Oxygen Species
Chemical activation
Molecules
DNA

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

ESI-MS/MS for the differentiation of diastereomeric pyrimidine glycols in mononucleosides. / Wang, Yinsheng; Vivekananda, Shetty; Zhang, Kangling.

In: Analytical Chemistry, Vol. 74, No. 17, 01.09.2002, p. 4505-4512.

Research output: Contribution to journalArticle

Wang, Yinsheng ; Vivekananda, Shetty ; Zhang, Kangling. / ESI-MS/MS for the differentiation of diastereomeric pyrimidine glycols in mononucleosides. In: Analytical Chemistry. 2002 ; Vol. 74, No. 17. pp. 4505-4512.
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N2 - Pyrimidine glycols, or 5,6-dihydroxy-5,6-dihydropyrimidines, are primary lesions in DNA induced by reactive oxygen species. In this article, we report the preparation and tandem mass spectrometry (MS/MS) characterization of the two cis diastereomers of the glycol lesions of 2′-deoxyuridine, 5-methyl-2′-deoxycytidine, and thymidine. Our results show that collisional activation of the [M + Na]+ ions of all the three pairs of cis isomers and that of the [M + H]+ ions of the 2′-deoxyuridine glycols and 5-methyl-2′-deoxycytidine glycols give a facile loss of a water molecule. Interestingly, the water loss occurs more readily for the 6S isomer than for the 6R isomer. Likewise, product ion spectra of the [M - H]- ions of the two cis isomers of the 2′-deoxyuridine glycols and thymidine glycols show more facile loss of water for the 6S isomer than for the 6R isomer. MS/MS acquired at different collisional energies gave similar results, which establishes the reproducibility of spectra.

AB - Pyrimidine glycols, or 5,6-dihydroxy-5,6-dihydropyrimidines, are primary lesions in DNA induced by reactive oxygen species. In this article, we report the preparation and tandem mass spectrometry (MS/MS) characterization of the two cis diastereomers of the glycol lesions of 2′-deoxyuridine, 5-methyl-2′-deoxycytidine, and thymidine. Our results show that collisional activation of the [M + Na]+ ions of all the three pairs of cis isomers and that of the [M + H]+ ions of the 2′-deoxyuridine glycols and 5-methyl-2′-deoxycytidine glycols give a facile loss of a water molecule. Interestingly, the water loss occurs more readily for the 6S isomer than for the 6R isomer. Likewise, product ion spectra of the [M - H]- ions of the two cis isomers of the 2′-deoxyuridine glycols and thymidine glycols show more facile loss of water for the 6S isomer than for the 6R isomer. MS/MS acquired at different collisional energies gave similar results, which establishes the reproducibility of spectra.

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