The Enzymatic Conversion of 5-Formyluracil to Uracil 5-Carboxylic Acid

Watanabe, Mutsumi; McCroskey, R.P.; Abbott, Mitchel T.

doi:10.1016/s0021-9258(18)63201-6

Cited by 29 publications

(5 citation statements)

References 17 publications

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“…According to this mechanism thymine ribonucleoside, succinate, and C02 are produced as a result of a peroxide anion of thymidine making a nucleophilic attack on the carbonyl carbon of a-ketoglutarate. A similar mechanism was postulated for the enzymatic reactions in which 5-hydroxymethyluracil and 5-formyl uracil are oxidized when it was realized that these reactions too are stimulated by molecular oxygen, -ketoglutarate, Fe2+, and ascorbate (Watanabe et al, 1970). The results of the 180 figure 5: The effect of catalase on the pyrimidine deoxyribonucleoside 2'-hydroxylase reaction.…”

Section: Discussionmentioning

confidence: 72%

“…-ketoglutarate enriched with 14C in both C-l and C-5, 1.0 and 1.0. The methods of synthesis, the purification, and the commercial sources of the above compounds have been reported (Watanabe et al, 1970;McCroskey et al, 1971). Catalase (beef liver, C-30), DEAE-cellulose, and bovine albumin were obtained from the Sigma Chemical Co.…”

Section: Methodsmentioning

confidence: 99%

“…uracil, thymine 7-hydroxylase reaction (Abbott et al, 1967); 5-hydroxymethyluracil to 5-formyluracil (Abbott et al, 1968); 5-formyluracil to uracil-5-carboxylic acid (Watanabe et al, 1970); and uracil-5-carboxylie acid to uracil and C02, uracil-5-carboxylic acid decarboxylase reaction (Palmatier et al, 1970). The 2'-hydroxylase, which catalyzes the first step in this pathway, also converts deoxyuridine to uridine and requires a-ketoglutarate, Fe2+, ascorbate (Shaffer et al, 1968), and 02 for activity (Shaffer et al, 1972).…”

mentioning

confidence: 99%

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Stoichiometry of the pyrimidine deoxyribonucleoside 2'-hydroxylase reaction and of the conversions of 5-hydroxymethyluracil to 5-formyluracil and of the latter to uracil-5-carboxylic acid

Liu¹,

Shaffer²,

Slaughter³

et al. 1972

Biochemistry

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Section: Discussionmentioning

confidence: 72%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Stoichiometry of the pyrimidine deoxyribonucleoside 2'-hydroxylase reaction and of the conversions of 5-hydroxymethyluracil to 5-formyluracil and of the latter to uracil-5-carboxylic acid

Liu¹,

Shaffer²,

Slaughter³

et al. 1972

Biochemistry

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“…or 5-formyluracil, but not thymidine, deoxyuridine, or deoxycytidine as a pyrimidine source. Moreover, it was suggested (16) that the pyrimidine deoxyribonucleoside 2-hydroxylation step (Fig. 1, reaction a) or the subsequent hydrolysis step (reaction b) might instead be affected in the uc-2-carrying strain.…”

mentioning

confidence: 99%

Metabolism of pyrimidine deoxyribonucleosides in Neurospora crassa

Shaffer¹,

Hsu²,

Abbott³

1975

J Bacteriol

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The experiments in this report involve the following series of reactions which were previously demonstrated with purified enzyme preparations from Neurospora crassa: thymidine a yields thymine ribonucleoside b yields thymine c yields 5-hydroxymethyluracil d yields 5-formyluracil e yields uracil-5-carboxylic acid f yields uracil. The evidence for some of the reactions occurring in vivo has been incomplete and for others totally lacking. In this paper intact cells of Neurospora are shown to be capable of converting the substrates of each of the reactions to the corresponding products. Studies are described which were carried out in vivo and in vitro with the pyrimidineless strains pyr-4,uc-1,uc-2 and pyr-4,uc-1,uc-3, developed by Williams and Mitchell. The results reported in the present paper indicate that (reaction a) and the uc-3 mutation affects thymine 7-hydroxylase (reactions c,d, and e). Evidence is presented for the 2'-hydroxylase reaction being the major, if not only, way by which Neurospora can initiate the conversion of thymidine to the pyrimidines of nucleic acids and for the 2'-hydroxylation of thymidine and deoxyuridine being catalyzed by the same enzyme. Deoxycytidine was shown not to be hydroxylated in intact cells but instead deaminated to deoxyuridine, which in turn was converted to uridine. Further studies with the uc-3-carrying strain showed that an enzyme other than thymine 7-hydroxylase can also convert 5-formyluracil to uracil-5-carboxylic acid.

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“…Temps de rétention: 4.6 min (acide oxo-2 valérique),et 1.6 min (acide butyrique).2.4. Epoxydation du cyclohexène par le ®-acide monopersuccini-0.1 gr d'acide monopersuccinique(16) titrant 95%,ont été adsorbés sur 2.4 gr de silica-gel,suivant le mode opératoire déjà décrit.A la poudre fine obtenue,on additionne 1 ml (0.81 gr,9.8 mmoles) de cyclohexène. Le mélange solide est agité pendant quatre heures ä la température ambiante.…”

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Decarboxylation Oxydative Des Acides Α-Cetoniques. Modeles Pour l'HYDROXYLATIONBIOLOGIQUE

Αγορίτσα-Εξάρχου¹

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The Enzymatic Conversion of 5-Formyluracil to Uracil 5-Carboxylic Acid

Cited by 29 publications

References 17 publications

Stoichiometry of the pyrimidine deoxyribonucleoside 2'-hydroxylase reaction and of the conversions of 5-hydroxymethyluracil to 5-formyluracil and of the latter to uracil-5-carboxylic acid

Stoichiometry of the pyrimidine deoxyribonucleoside 2'-hydroxylase reaction and of the conversions of 5-hydroxymethyluracil to 5-formyluracil and of the latter to uracil-5-carboxylic acid

Metabolism of pyrimidine deoxyribonucleosides in Neurospora crassa

Decarboxylation Oxydative Des Acides Α-Cetoniques. Modeles Pour l'HYDROXYLATIONBIOLOGIQUE

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