Enhancement of Enantioselectivity in the Optical Resolution of Primary Alcohols with Modified Cyclodextrin Colyophilized Lipase

Abstract

Colyophilization of lipase was carried out with immobilized β‐cyclodextrins (β‐CyD) bearing methyl, acetyl, benzoyl, and nicotinoyl substituents. The colyophilizates enhanced stereoselectivity in the acylation of several alcohols. The enantioselectivity in the acylation of ethyl‐1‐hydroxymethyl‐phenylphosphine oxide using colyophilized lipase with nicotinoyl‐β‐CyD increased approximately threefold (from E=34 to E=113). The amphiphilic character of modified CyDs has been found to influence the enhancement of enantioselectivity.

Keywords:

• lipase
• modified cyclodextrin
• optical resolution
• primary alcohols