Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein.
Phytochemistry
; 69(18): 3038-42, 2008 Dec.
Article
en En
| MEDLINE
| ID: mdl-18639908
ABSTRACT
The terpenoid gossypol, a secondary metabolite found in the cotton plant, is synthesized by a free radical dimerization of hemigossypol. Gossypol exists as an atropisomeric mixture because of restricted rotation around the central binaphthyl bond. The dimerization of hemigossypol is regiospecific in cotton. In the case of some moco cotton, the dimerization also exhibits a high level of stereoselectivity. The mechanism that controls this stereoselective dimerization is poorly understood. In this paper, we demonstrate that a dirigent protein controls this stereoselective dimerization process. A partially purified protein preparation from cotton flower petals, which by itself is unable to convert hemigossypol to gossypol, converts hemigossypol with a 30% atropisomeric excess into (+)-gossypol when combined with an exogenous laccase, which by itself produces racemic gossypol.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Proteínas de Plantas
/
Gosipol
/
Gossypium
Idioma:
En
Revista:
Phytochemistry
Año:
2008
Tipo del documento:
Article
País de afiliación:
Estados Unidos