Enzyme-Catalyzed Asymmetric Domino Thia-Michael/Aldol Condensation Using Pepsin.
J Org Chem
; 81(14): 6042-8, 2016 07 15.
Article
en En
| MEDLINE
| ID: mdl-27348476
ABSTRACT
The novel catalytic promiscuity of pepsin from porcine gastric mucosa for the asymmetric catalysis of the domino thia-Michael/aldol condensation reaction in MeCN and buffer was discovered for the first time. Broad substrate specificity was tested, and a series of corresponding products were obtained with enantioselectivities of up to 84% ee. This specific catalysis was demonstrated by using recombinant pepsin and control experiments with denatured and inhibited pepsin. The reaction was also shown to occur in the active site by site-directed mutagenesis (the Asp32Ala mutant of pepsin), and a possible mechanism was proposed.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Catálisis
/
Pepsina A
/
Aldehídos
/
Enzimas
Límite:
Animals
Idioma:
En
Revista:
J Org Chem
Año:
2016
Tipo del documento:
Article