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Characterization of N ‐succinyl metabolites of adenine and aminoimidazole carboxamide by mass spectrometry
Author(s) -
McCloskey James A.,
Barnes Larry B.,
Crain P. F.,
Lyman K. J.,
Bishop Stephen H.
Publication year - 1975
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.1200020205
Subject(s) - chemistry , carboxamide , mass spectrometry , stereochemistry , nucleoside , aspartic acid , imidazole , moiety , phosphate , nucleotide , adenine nucleotide , amino acid , chromatography , biochemistry , gene
N 6 ‐(2‐succinyl)adenosine 5′‐phosphate and N ‐(5‐amino‐1‐ribosyl‐4‐imidazole carbonyl)‐ L ‐aspartic acid ′‐phosphate were prepared enzymatically using adenylosuccinate lyase (EC 4.3.2.2) isolated from human erythrocytes. N 6 ‐(2‐succinyl)adenosine 5′‐phosphate, N ‐(5‐amino‐1‐ribosyl‐4‐imidazole carbonyl)‐ L ‐aspartic acid 5′‐phosphate and N ‐(5‐amino‐1‐ribosyl‐4‐imidazole carboxamide) 5′‐phosphate and the nucleoside and free base analogs of these nucleotides were converted to the trimethylsilyl derivatives and characterized by mass spectrometry. The extent of the trimethylsilylation was greater for adenine substituted compounds compared with those related to aminoimidazole carboxamide. Major mass spectral fragment ions correspond to the intact base plus portions of the sugar skeleton and to electron impact‐induced decomposition products of the sugar moiety. Succinyl substitution at N 6 of the adenine derivatives leads to characteristic loss of CO 2 SiMe 3 from the molecular ion. A combination of liquid chromatographic procedures and gas chromatography mass spectrometry gave rapid and unequivocal identification of succinyladenine from human urine.