A Catalyst from Burkholderia cenocepacia for Efficient Anti-Prelog's Bioreduction of 3,5-Bis(Trifluoromethyl) Acetophenone.
Appl Biochem Biotechnol
; 184(4): 1319-1331, 2018 Apr.
Article
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| MEDLINE
| ID: mdl-29022160
ABSTRACT
(R)-3, 5-Bis(trifluoromethyl)phenyl ethanol is a key chiral intermediate for the synthesis of aprepitant. Through a genome mining approach, an NADPH-dependent short-chain dehydrogenases derived from Burkholderia cenocepacia (Bc-SDR) was discovered with excellent anti-Prelog's stereoselectivity of reducing 3, 5-bis(trifluoromethyl) acetophenone. The enzyme with 247 amino acids was successfully expressed in Escherichia coli and the molecular weight was about 26 kDa. Optimization of reaction conditions showed that the optimum temperature and pH of the enzyme was 25 °C and pH 7.0, respectively. Strong enhancement of enzyme activity was observed in the presence of 1 mM Mn2+. In addition, Bc-SDR exhibited (R)-selective enantioselectivity toward acetophenone derivatives, which makes it a potential catalyst for obtaining aromatic chiral alcohols as useful blocks in pharmaceutical applications.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Contexto en salud:
3_ND
Problema de salud:
3_neglected_diseases
/
3_zoonosis
Asunto principal:
Oxidorreductasas
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Acetofenonas
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Proteínas Bacterianas
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Escherichia coli
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Burkholderia cenocepacia
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Hidrocarburos Fluorados
Idioma:
En
Revista:
Appl Biochem Biotechnol
Año:
2018
Tipo del documento:
Article