N-Nmoc-L-glutamate, a new caged glutamate with high chemical stability and low pre-photolysis activity.
J Biol Chem
; 272(52): 32933-9, 1997 Dec 26.
Article
en En
| MEDLINE
| ID: mdl-9407072
ABSTRACT
We report the synthesis, the physicochemical characterization, and biological evaluation of a new caged glutamate, N-(o-nitromandelyl)oxycarbonyl-L-glutamic acid (Nmoc-Glu), that liberates free glutamate on photolysis. The low affinity of certain glutamate receptors and their rapid entry into desensitization have effectively prevented the creation of an ideal caged glutamate. In the absence of an ideal compound, Nmoc-Glu was designed to resist spontaneous hydrolysis while maintaining reasonable photorelease yield and kinetics. Chemical and physiological analyses reveal that Nmoc-Glu, indeed, has exceptionally low residual activity and high chemical stability. The quantum yield of Nmoc-Glu is 0.11. Photolytic uncaging and release of free glutamate occur in two steps, consisting of an initial light-induced cleavage that proceeds on the sub-millisecond time scale, and a subsequent light-independent, pH-dependent decarboxylation step that proceeds on the millisecond time scale. The low residual activity and high chemical stability of Nmoc-Glu are important advantages in applications where pre-photolysis Glu receptor activation and desensitization must be minimized.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Fotólisis
/
Glutamatos
Límite:
Animals
Idioma:
En
Revista:
J Biol Chem
Año:
1997
Tipo del documento:
Article
País de afiliación:
Estados Unidos