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Syntheses of [5‐ 2 H]‐uracil, [5‐ 2 H]‐cytosine, [6‐ 2 H]‐uracil and [6‐ 2 H]‐cytosine
Author(s) -
Kiritani Reiko,
Asano Takeyoshi,
Fujita ShinIchi,
Dohmaru Takaaki,
Kawanishi Tetsuro
Publication year - 1986
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580230211
Subject(s) - uracil , cytosine , chemistry , catalysis , tritium , dna , organic chemistry , biochemistry , physics , nuclear physics
Facile syntheses of [5‐ 2 H]‐, [6‐ 2 H]‐uracil and [5‐ 2 H]‐, [6‐ 2 H]‐cytosine were investigated. The catalytic reaction of uracil or cytosine with 2 H 2 gas in alkaline media gave rise to [6‐ 2 H]‐compounds almost exclusively. On the other hand,the reaction of 5‐bromouracil or 5‐bromocytosine with 2 H 2 gas and gave rise to a mixture of [5‐ 2 H]‐, [6‐ 2 H]‐ and [5‐ 2 H,6‐ 2 H]‐compounds depending on the experimental conditions. By controlling the temperature, the pressure of 2 H 2 gas and the amounts of catalyst, [5‐ 2 H]‐uracil and [5‐ 2 H]‐cytosine were obtained. The isotopic distribution in each product was measured by 1 H NMR spectroscopy combined with an HPLC method.