Jump to main content
Jump to site search


Ionic-surfactant-coated subtilisin: activity, enantioselectivity, and application to dynamic kinetic resolution of secondary alcohols

Author affiliations

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.

Graphical abstract: Ionic-surfactant-coated subtilisin: activity, enantioselectivity, and application to dynamic kinetic resolution of secondary alcohols

Back to tab navigation

Supplementary files

Publication details

The article was received on 31 Aug 2017, accepted on 10 Oct 2017 and first published on 10 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02181J
Citation: Org. Biomol. Chem., 2017, Advance Article
  •   Request permissions

    Ionic-surfactant-coated subtilisin: activity, enantioselectivity, and application to dynamic kinetic resolution of secondary alcohols

    K. Kim, E. Lee, C. Kim, J. Park and M. Kim, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02181J

Search articles by author

Spotlight

Advertisements