Related Experiment Video
Updated: Feb 20, 2026
Unraveling Entropic Rate Acceleration Induced by Solvent Dynamics in Membrane Enzymes
Published on: January 16, 2016
Ionic-surfactant-coated subtilisin: activity, enantioselectivity, and application to dynamic kinetic resolution of
Kyungwoo Kim1, Eungyeong Lee, Cheolwoo Kim
1Department of Chemistry, Pohang University of Science and Technology, 77 Cheongam-ro, Pohang 37673, Republic of Korea. pjw@postech.ac.kr mjkim@postech.ac.kr.
Abstract:
In this work, we explored the utility of ionic-surfactant-coated Bacillus licheniformis subtilisin (ISCBLS) as the catalyst for the dynamic kinetic resolution of secondary alcohols. ISCBLS was prepared by freeze-drying Bacillus licheniformis subtilisin with both ionic surfactant 1 and dextrin. ISCBCL displayed 9300-fold enhanced activity relative to its native counterpart in the transesterificaion of N-acetyl phenylalanine ethyl ester with 1-propanol in hexane and 12 800-fold enhanced activity in the transesterification of trifluoroethyl butyrate with 1-phenylethanol in THF. The enantioselectivity of ISCBLS was examined with 50 secondary alcohols as the substrates for kinetic resolution in the presence of trifluoroethyl butyrate. ISCBLS displayed synthetically useful enantioselectivity for most of the secondary alcohols tested. The enantioselectivity of ISCBLS was in particular good to high for m- or p-substituted 1-phenylethanols. The DKRs of these secondary alcohols by the combination of ISCBLS and a ruthenium-based racemization catalyst provided the products of (S)-configuration with good results (80-94% yield, 90-99% ee). It is concluded that ISCBLS is of great use as the enantiocomplementary counterpart of (R)-selective lipase for the dynamic kinetic resolution of secondary alcohols.
Related Concept Videos
02:57Sharpless Epoxidation
02:48Conversion of Alcohols to Alkyl Halides
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
02:23SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
01:38Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...