Enantioselective transacetylation of (R,S)-beta-citronellol by propanol rinsed immobilized Rhizomucor miehei lipase.
BACKGROUND
Use of enzymes in low water media is now widely used for synthesis and kinetic resolution of organic compounds. The frequently used enzyme form is the freeze-dried powders. It has been shown earlier that removal of water molecules from enzyme by rinsing with n-propanol gives preparation (PREP) which show higher activity in low water media. The present work evaluates PREP of the lipase (from Rhizomucor miehei) for kinetic resolution of (R,S)-beta-citronellol. The acylating agent was vinyl acetate and the reaction was carried out in solvent free media.


RESULTS
The PREP, with 0.75% (v/v, reaction media) water, was indeed found to be more efficient and gave 95% conversion to the ester. Using this PREP, with no added water, 90% ee for (R)-(+)-beta-citronellyl acetate at 45% conversion (E = 42) was obtained in 4 h. The control with freeze-dried enzyme, with zero water content, gave 78% ee at 30% conversion (E = 13). FT-IR analysis showed that PREP had retained the alpha-helical content of the enzyme. On the other hand, freeze-dried enzyme showed considerable loss in the alpha-helical content.


CONCLUSIONS
The results show that PREP may be a superior biocatalyst for enantioselective conversion by enzymes in low-water media.
Majumder
Abir B
AB
Chemistry Department, Indian Institute of Technology Delhi, Hauz Khas, New Delhi, India. aabir.majumder@gmail.com
Shah
Shweta
S
Gupta
Munishwar N
MN