Scavenging of NO by Melatonin

TURJANSKI, A; LEONIK, F.; ESTRIN, D.; ROSENSTEIN, R.E; DOCTOROVICH, F.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Año: 2000 vol. 122 p. 10468 - 10469

0002-7863

The main product of the reaction of melatonin with NO in the presence of O2 in aprotic and aqueous media, N-nitrosomelatonin, was isolated and characterized by 1H NMR and X-ray spectroscopy8 (Figure 1). The density functional theory (DFT)-optimized structure at the generalized gradient approximation (GGA) Becke-Perdew level9 is in good agreement with experimental results. In solution, N-nitrosomelatonin is present in two isomeric forms, with O3-N3-N1-C9 dihedral angles of 0° and 180°. The isomerization barrier ¢G# 330 was found to be 16 kcal mol-1 by variable-temperature 1H NMR.2 in aprotic and aqueous media, N-nitrosomelatonin, was isolated and characterized by 1H NMR and X-ray spectroscopy8 (Figure 1). The density functional theory (DFT)-optimized structure at the generalized gradient approximation (GGA) Becke-Perdew level9 is in good agreement with experimental results. In solution, N-nitrosomelatonin is present in two isomeric forms, with O3-N3-N1-C9 dihedral angles of 0° and 180°. The isomerization barrier ¢G# 330 was found to be 16 kcal mol-1 by variable-temperature 1H NMR.