Asymmetric oxidoreductions catalyzed by alcohol dehydrogenase in organic solvents

Journal Article · Wed Oct 15 00:00:00 EDT 1986 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00281a044· OSTI ID:7245563

Grunwald, J; Wirz, B; Scollar, M P; Klibanov, A M

A methodology is developed for the use of alcohol dehydrogenase (and other NAD/sup +//NADH-dependent enzymes) as catalysts in organic solvents. The enzyme and the cofactor are deposited onto the surface of glass beads which are then suspended in a water-immiscible organic solvent containing the substrate. Both NADH and NAD/sup +/ are efficiently regenerated in such a system with alcohol dehydrogenase-catalyzed oxidation of ethanol and reduction of isobutyraldehyde, respectively; cofactor turnover numbers of 10/sup 5/ to greater than 10/sup 6/ have been obtained. With use of asymmetric oxidoreductions catalyzed by horse liver alcohol dehydrogenase in isopropyl ether, optically active (ee of 95 to 100%) alcohols and ketones have been prepared on a 1 to 10 mmol scale.

• Research Organization: Massachusetts Institute of Technology, Cambridge
• OSTI ID: 7245563
• Journal Information: J. Am. Chem. Soc.; (United States), Vol. 108:21
• Country of Publication: United States
• Language: English

Related Subjects

10 SYNTHETIC FUELS
ALCOHOLS
CHEMICAL PREPARATION
ALDEHYDES
REDUCTION
ETHANOL
OXIDATION
KETONES
OXIDOREDUCTASES
CATALYTIC EFFECTS
CATALYSIS
CATALYSTS
EXPERIMENTAL DATA
ORGANIC SOLVENTS
CHEMICAL REACTIONS
DATA
ENZYMES
HYDROXY COMPOUNDS
INFORMATION
NUMERICAL DATA
ORGANIC COMPOUNDS
SOLVENTS
SYNTHESIS
090221* - Alcohol Fuels- Chemical Synthesis- (1976-1989)