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A theoretical and mass spectrometry study of the novel mechanism of N-glycosidic bond cleavage in nucleoside

文献类型： 外文期刊

作者： Liu, Jihong 1 ; Cao, Shuxia 1 ; Jia, Bin 2 ; Wei, Donghui 1 ; Liao, Xincheng 1 ; Lu, Jiansha 1 ; Zhao, Yufen 1 ;

作者机构： 1.Zhengzhou Univ, Dept Chem, Key Lab Chem Biol & Organ Chem, Zhengzhou 450052, Peoples R China

2.Henan Acad Agr Sci, Res Ctr Agr Qual Stand & Testing Tech, Zhengzhou 450002, Peoples R China

3.Tsinghua Univ, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Dept Chem, Beijing 100084, Peoples R China

关键词： Nucleoside;Fragmentation mechar ism;ESI;Theoretical calculations

期刊名称：INTERNATIONAL JOURNAL OF MASS SPECTROMETRY （ 影响因子：1.986； 五年影响因子：1.799 ）

ISSN： 1387-3806

年卷期： 2009 年 282 卷 1-2 期

页码：

收录情况： SCI

摘要： The fragmentation pathways of ribonucleosides, deoxynucleosides and isopropylidenenucleosides were investigated by electrospray ionization tandem mass spectrometry (ESI-MS/MS) in both positive and negative mode. Novel fragmentation pathways investigated using deuterium-label experiment provided important insight on the nature of N-glycosidic bond cleavage. The deuterium of 5'-hydroxyl group on ribose moiety was deprived by the nucleobase, and a novel five-member ring through T-oxygen and V-carbon was formed in the ribose residue as the lost neutral molecule, instead of a new double bond generating between V-C and 2'-C as the literature reported. The novel fragmentation pathway was supported by density functional theory calculations. (C) 2009 Published by Elsevier B.V.

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