Synthesis of syn and anti isomers of trans-cyclopropyl arginine.
J Org Chem
; 67(7): 2352-4, 2002 Apr 05.
Article
en En
| MEDLINE
| ID: mdl-11925253
ABSTRACT
There is currently considerable interest in arginine and its structural analogues in the context of nitric oxide synthase (NOS) substrates and inhibitors. Of particular interest are conformationally constrained arginine analogues used to probe the active sites of the three NOS isoforms. A simple procedure is described for the preparation of syn- and anti-trans-cyclopropyl arginine starting from the alpha-OBO-protected Cbz-dehydroglutamate. Cyclopropanation is effected by diazomethane addition followed by irradiation of the resulting pyrazoline and gives a 31 mixture of synanti isomers that can be separated by crystallization. Reduction of the ester to the alcohol followed by guanylation gives the fully protected cyclopropyl arginine analogues. The CBZ protecting groups are removed by hydrogenolysis and the OBO by mild acid treatment followed by base hydrolysis.
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Bases de datos:
MEDLINE
Asunto principal:
Arginina
Idioma:
En
Revista:
J Org Chem
Año:
2002
Tipo del documento:
Article
País de afiliación:
Canadá