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On the oxidation of N ‐methyl and N ‐benzylpyrimidin‐2‐ and ‐4‐ones by rabbit liver aldehyde oxidase
Author(s) -
Angelino S. A. G. F.,
Buurman D. J.,
van der Plas H. C.,
Müller F.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210323
Subject(s) - chemistry , aldehyde , substituent , aldehyde oxidase , yield (engineering) , oxidase test , enzyme , methyl group , uracil , stereochemistry , medicinal chemistry , catalysis , organic chemistry , biochemistry , group (periodic table) , xanthine oxidase , dna , materials science , metallurgy
The presence of a methyl or benzyl group at N‐1 or N‐3 of 2‐ and 4‐pyrimidone does not affect the site of oxidation by rabbit liver aldehyde oxidase. From all substrates studies only one product viz . the corresponding N‐1 or N‐3 substituted uracil has been obtained. The maximum rates of oxidation by free enzyme show an optimum in the p H range 6.5–7.8, which is little influenced by the site and the size of the N‐substituent. Application of immobilized enzyme in small scale synthesis gives 1‐ or 3‐R‐uracils (R = methyl, benzyl) in 43–78% yield.