Synthesis of (R)-mellein by a partially reducing iterative polyketide synthase.
J Am Chem Soc
; 134(29): 11924-7, 2012 Jul 25.
Article
en En
| MEDLINE
| ID: mdl-22793256
ABSTRACT
Mellein and the related 3,4-dihydroisocoumarins are a family of natural products with interesting biological properties. The mechanisms of dihydroisocoumarin biosynthesis remain largely speculative today. Here we report the synthesis of mellein by a partially reducing iterative polyketide synthase (PR-PKS) as a pentaketide product. Remarkably, despite the head-to-tail homology shared with several fungal and bacterial PR-PKSs, the mellein synthase exhibits a distinct keto reduction pattern in the synthesis of the pentaketide. We present evidence to show that the ketoreductase (KR) domain alone is able to recognize and differentiate the polyketide intermediates, which provides a mechanistic explanation for the programmed keto reduction in these PR-PKSs.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Actinomycetales
/
Sintasas Poliquetidas
/
Ocratoxinas
Idioma:
En
Revista:
J Am Chem Soc
Año:
2012
Tipo del documento:
Article