Asymmetric bioreduction of keto groups of 4- and 5-Oxodecanoic acids/esters with a new carbonyl reductase

• Published in: Catalysis communications Vol. 102; pp. 35 - 39
• Main Authors: Zhang, Chao, Pan, Jiang, Li, Chun-Xiu, Bai, Yun-Peng, Xu, Jian-He
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.12.2017
• Subjects: (R)-γ-Decalactone; (R)-δ-Decalactone; 4-Oxodecanoic acid; 5-Oxodecanoic acid; Asymmetric reduction; Carbonyl reductase; Asymmetric reduction; (R)-γ-Decalactone; Carbonyl reductase; 4-Oxodecanoic acid; (R)-δ-Decalactone; 5-Oxodecanoic acid
• ISSN: 1566-7367; 1873-3905
• DOI: 10.1016/j.catcom.2017.08.023

A novel carbonyl reductase from Serratia marcescens, SmCR, was successfully cloned and overexpressed in Escherichia coli. SmCR could catalyze the asymmetric reduction of long-chain keto acids/esters containing remote carbonyl groups, such as 4-oxo- and 5-oxodecanoic acids, yielding chiral γ- and δ-decalactones with high enantiopurity (up to 99% ee). This is the first report of enzymatic synthesis of (R)-γ- and (R)-δ-decalactones starting from γ-, δ-keto acids using free enzymes. [Display omitted] •A new carbonyl reductase, named SmCR, was successfully overexpressed in E. coli.•SmCR can asymmetrically reduce 4-oxo- and 5-oxodecanoic acids with high enantioselectivity.•(R)-γ-decalactone in 99% ee and (R)-δ-decalactone in 95% ee with 72–79% yields were obtained.