A theoretical and mass spectrometry study of the novel mechanism of N-glycosidic bond cleavage in nucleoside
| Autor: | Jiansha Lu, Donghui Wei, Ji-Hong Liu, Bin Jia, Xin-Cheng Liao, Yufen Zhao, Shuxia Cao |
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| Rok vydání: | 2009 |
| Předmět: |
chemistry.chemical_classification
Double bond Collision-induced dissociation Stereochemistry Electrospray ionization Analytical chemistry Glycosidic bond Condensed Matter Physics Tandem mass spectrometry Nucleobase chemistry Fragmentation (mass spectrometry) Physical and Theoretical Chemistry Instrumentation Spectroscopy Bond cleavage |
| Zdroj: | International Journal of Mass Spectrometry. 282:1-5 |
| ISSN: | 1387-3806 |
| DOI: | 10.1016/j.ijms.2009.01.003 |
| Popis: | 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 5′-oxygen and 1′-carbon was formed in the ribose residue as the lost neutral molecule, instead of a new double bond generating between 1′-C and 2′-C as the literature reported. The novel fragmentation pathway was supported by density functional theory calculations. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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