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Differentiation of isomeric 2′‐, 3′‐ and 5′‐deoxynucleosides by electron ionization and chemical ionization‐linked scanning mass spectrometry
Author(s) -
Reimer Mark L. J.,
McClure Thomas D.,
Schram Karl H.
Publication year - 1989
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200180804
Subject(s) - chemistry , fragmentation (computing) , electron ionization , ion , chemical ionization , mass spectrum , mass spectrometry , ionization , trimethylsilyl , deoxyadenosine , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , chromatography , enzyme , computer science , operating system
A comparative mass spectral examination of the trimethylsilyl (TMS) derivatives of 2′‐, 3′‐ and 5′‐deoxyadenosine, 2′‐, 3′‐ and 5′‐deoxyguanosine, 2′‐, 3′‐ and 5′‐deoxyxanothosine and 2′‐ and 5′‐deoxy‐2‐fluoroadenosine is presented. A general compilation of the major fragment ions found in the low‐resolution electron ionization (EI) spectra of the eleven deoxynucleosides is given. Chemical ionization (CI)–collisional activation (CA) daughter ion spectra are reported using the deoxyadenosines as model compounds. Ion structures and fragmentation pathways are proposed for those ions characteristic of each of the isomers. Significant differences in fragmentation exist between the isomeric 2′‐, 3′‐ and 5′‐purine deoxynucleosides. The formation and structures of ten ions important in this differentiation are discussed. The CI–CA linked scan spectra provide complementary structural information relative to the EI mass spectra.