INIFTA   05425
INSTITUTO DE INVESTIGACIONES FISICO-QUIMICAS TEORICAS Y APLICADAS
Unidad Ejecutora - UE
artículos
Título:
Stability of 7,8-dihydropterins in air-equilibrated aqueous solutions
Autor/es:
: M. LAURA DÁNTOLA, MARIANA VIGNONI, ALBERTO L. CAPPARELLI, CAROLINA LORENTE, ANDRÉS H. THOMAS
Revista:
HELVETICA CHIMICA ACTA
Editorial:
Verlag Helvetica Chimica Acta
Referencias:
Año: 2008 vol. 91 p. 411 - 425
ISSN:
0018-019X
Resumen:
6-Substituted 7,8-dihydropterins (¼2-amino-7,8-dihydropteridin-4(1H)-ones) are heterocyclic compounds
that occur in a wide range of living systems and participate in relevant biological functions. In airequilibrated
aqueous solutions, these compounds react with dissolved O2 (autooxidation). The rates of
these reactions as well as the products formed strongly depend on the chemical structure of the
substituents. 7,8-Dihydro-6-methylpterin and 7,8-dihydro-6,7-dimethylpterin that bear electron-donor
groups as substituents are the most reactive derivatives and undergo oxidation of the pterin moiety to
yield the corresponding oxidized derivatives (6-methylpterin and 6,7-dimethylpterin, resp.). The
oxidations of 7,8-dihydrobiopterin, 7,8-dihydroneopterin, and 7,8-dihydrofolic acid are slower, and they
yield 7,8-dihydroxanthopterin as the main product. 7,8-Dihydroxanthopterin, 6-formyl-7,8-dihydropterin,
and sepiapterin are rather stable, and their consumption in air-equilibrated solutions is negligible for
several days. The pseudo-first-order rate constants of the reactions between these compounds and O2 at
258 and 408 are reported. The biological implications of the results obtained are also discussed.¼2-amino-7,8-dihydropteridin-4(1H)-ones) are heterocyclic compounds
that occur in a wide range of living systems and participate in relevant biological functions. In airequilibrated
aqueous solutions, these compounds react with dissolved O2 (autooxidation). The rates of
these reactions as well as the products formed strongly depend on the chemical structure of the
substituents. 7,8-Dihydro-6-methylpterin and 7,8-dihydro-6,7-dimethylpterin that bear electron-donor
groups as substituents are the most reactive derivatives and undergo oxidation of the pterin moiety to
yield the corresponding oxidized derivatives (6-methylpterin and 6,7-dimethylpterin, resp.). The
oxidations of 7,8-dihydrobiopterin, 7,8-dihydroneopterin, and 7,8-dihydrofolic acid are slower, and they
yield 7,8-dihydroxanthopterin as the main product. 7,8-Dihydroxanthopterin, 6-formyl-7,8-dihydropterin,
and sepiapterin are rather stable, and their consumption in air-equilibrated solutions is negligible for
several days. The pseudo-first-order rate constants of the reactions between these compounds and O2 at
258 and 408 are reported. The biological implications of the results obtained are also discussed.2 (autooxidation). The rates of
these reactions as well as the products formed strongly depend on the chemical structure of the
substituents. 7,8-Dihydro-6-methylpterin and 7,8-dihydro-6,7-dimethylpterin that bear electron-donor
groups as substituents are the most reactive derivatives and undergo oxidation of the pterin moiety to
yield the corresponding oxidized derivatives (6-methylpterin and 6,7-dimethylpterin, resp.). The
oxidations of 7,8-dihydrobiopterin, 7,8-dihydroneopterin, and 7,8-dihydrofolic acid are slower, and they
yield 7,8-dihydroxanthopterin as the main product. 7,8-Dihydroxanthopterin, 6-formyl-7,8-dihydropterin,
and sepiapterin are rather stable, and their consumption in air-equilibrated solutions is negligible for
several days. The pseudo-first-order rate constants of the reactions between these compounds and O2 at
258 and 408 are reported. The biological implications of the results obtained are also discussed.2 at
258 and 408 are reported. The biological implications of the results obtained are also discussed.8 and 408 are reported. The biological implications of the results obtained are also discussed.