CO2-expanded bio-based liquids as novel solvents for enantioselective biocatalysis. Issue 20 (18th May 2017)

• Record Type: Journal Article
• Authors: Hoang, Hai Nam; Nagashima, Yoshihiro; Mori, Shuichi; Kagechika, Hiroyuki; Matsuda, Tomoko
• Is Part Of: Tetrahedron. Volume 73:Issue 20(2017)
• Page Start: 2984
• Page End: 2989
• Publication Date: 2017-05-18
• Subjects: CO2-expanded bio-based liquids -- Alternative solvents -- Bulky secondary alcohols -- Lipase-catalyzed transesterification -- Kinetic resolution; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.04.024
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: For the first time, CO2 -expanded bio-based liquids were reported as novel and sustainable solvents for biocatalysis. Herein, it was found that by expansion with CO2, 2-methyltetrahydrofuran (MeTHF), and other bio-based liquids, which were not favorable solvents for immobilized Candida antarctica lipase B (Novozym 435) catalyzed transesterification, were tuned into excellent reaction media. Especially, for the kinetic resolution of challenging bulky secondary substrates such as rac -1-adamantylethanol, the lipase displayed very high activity with excellent enantioselectivity ( E value > 200) in CO2 -expanded MeTHF (MeTHF concentration 10% v/v, 6 MPa), whereas there was almost no activity observed in conventional organic solvents. Graphical abstract: