Enzymatic synthesis of (R) and (S) 1-deuterohexanol

This paper describes practical enzymatic procedures for the synthesis of (R) and (S) 1-deuterohexanol, a useful building block for chiral poly isocyanated liquid crystals. Alcohol dehydrogenases from horse liver and Pseudomonas catalyzed the reduction of hexanal with deuterated NAD (NADD) resulting...

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Bibliographic Details
Published in:Applied biochemistry and biotechnology 1992-04, Vol.33 (1), p.15-24
Main Authors: BRADSHAW, C. W, LALONDE, J. J, CHI-HUEY WONG
Format: Article
Language:English
Subjects:
1-deuterohexanol
alcohol dehydrogenase
Alcohol Dehydrogenase - chemistry
Aldehydes - chemical synthesis
Biological and medical sciences
Biotechnology
Deuterium
enantiomers
enzymatic synthesis
Fundamental and applied biological sciences. Psychology
Heterocyclic Compounds - chemical synthesis
Hexanols - chemical synthesis
horses
Immobilization of enzymes and other molecules
Immobilization techniques
immobilized enzymes
liver
Methods. Procedures. Technologies
Molecular Structure
NAD - chemistry
Oxidation-Reduction
Pseudomonas
Stereoisomerism
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Summary:This paper describes practical enzymatic procedures for the synthesis of (R) and (S) 1-deuterohexanol, a useful building block for chiral poly isocyanated liquid crystals. Alcohol dehydrogenases from horse liver and Pseudomonas catalyzed the reduction of hexanal with deuterated NAD (NADD) resulting in 50% and 89% yields of (R) and (S) 1-deuterohexanol, respectively. The deuterated cofactor was regenerated in situ by alcohol dehydrogenase catalyzed oxidation of ethanol-d6 or 2-propanol-d8. The (S) alcohol was also synthesized by the horse liver alcohol dehydrogenase reduction of 1-deuterohexanal, which was prepared chemically from hexanal. The yields of the reaction were greatly increased by the use of a biphasic system or with the immobilized enzyme in anhydrous organic solvents. Horse liver alcohol dehydrogenase was stabilized by immobilization on PAN or noncovalent entrapment on XAD resin.
ISSN:0273-2289
1559-0291
DOI:10.1007/bf02922180