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Mass spectral characterization of some nucleoside phosphordiamidates
Author(s) -
Tamás József,
Tomasz Jenö
Publication year - 1985
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200120907
Subject(s) - mass spectrum , chemistry , amide , trimethylsilyl , thermal decomposition , decomposition , ion , electron ionization , nucleoside , evaporation , organic chemistry , analytical chemistry (journal) , stereochemistry , ionization , physics , thermodynamics
Abstract The electron impact (EI) mass spectrometric behaviour of 11 recently synthesized 5′‐phosphordiamidates with various bases and amidate groups has been studied by low and high resolution techniques. Trimethylsilylation of these compounds yields derivatives which are sufficiently volatile for direct evaporation in the ion source. Structural relationships for the main fragment ions are given and compared with those of the previously studied analogous trimethylsilylated mononucleotides. Decomposition routes related to and specific for the primary, secondary or tertiary character of the amide functions were observed. Tertiary diamidates studied were found to be evaporable in underivatized form without significant thermal decomposition and gave very simple spectra with characteristic fragments for the base and the sugar, as well as the phosphordiamidate moieties. The mass spectra of trimethylsilyl (TMS) derivatives of some 3′ and 5′‐isomers were compared and found to be characteristically different.