120374-94-9

Basic information

• Product Name: (S)-3-Hydroxy-butyric acid pentyl ester
• CAS NO: 120374-94-9
• Molecular Weight: 174.24
• Mol File: 120374-94-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-3-Hydroxy-butyric acid pentyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Hydroxy-butyric acid pentyl ester(120374-94-9)
• EPA Substance Registry System: (S)-3-Hydroxy-butyric acid pentyl ester(120374-94-9)

Safety Data

• Hazardous Substances Data: 120374-94-9(Hazardous Substances Data)

Upstream product

• 6624-84-6 pentyl acetoacetate 

Relevant articles and documents

Single-Point Mutant Inverts the Stereoselectivity of a Carbonyl Reductase toward β-Ketoesters with Enhanced Activity

Enzyme stereoselectivity control is still a major challenge. To gain insight into the molecular basis of enzyme stereo-recognition and expand the source of antiPrelog carbonyl reductase toward β-ketoesters, rational enzyme design aiming at stereoselectivity inversion was performed. The designed variant Q139G switched the enzyme stereoselectivity toward β-ketoesters from Prelog to antiPrelog, providing corresponding alcohols in high enantiomeric purity (89.1–99.1 % ee). More importantly, the well-known trade-off between stereoselectivity and activity was not found. Q139G exhibited higher catalytic activity than the wildtype enzyme, the enhancement of the catalytic efficiency (kcat/Km) varied from 1.1- to 27.1-fold. Interestingly, the mutant Q139G did not lead to reversed stereoselectivity toward aromatic ketones. Analysis of enzyme–substrate complexes showed that the structural flexibility of β-ketoesters and a newly formed cave together facilitated the formation of the antiPrelog-preferred conformation. In contrast, the relatively large and rigid structure of the aromatic ketones prevents them from forming the antiPrelog-preferred conformation.

Biochemical reduction of 3-oxoalkanoic esters by a bottom-fermentation yeast, Saccharomyces cerevisiae IFO 0565

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