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 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.
Bradshaw
C W
CW
Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037.
Lalonde
J J
JJ
Wong
C H
CH
D000426:Alcohol Dehydrogenase / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis; D003903:Deuterium; D006571:Heterocyclic Compounds / Q000138:chemical synthesis; D000441:Hexanols / Q000138:chemical synthesis*; D015394:Molecular Structure; D009243:NAD / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000447:Aldehydes; D006571:Heterocyclic Compounds; D000441:Hexanols; D009243:NAD; C077043:hexanal-1,3-dithiane; C010463:n-hexanal; D003903:Deuterium; D000426:Alcohol Dehydrogenase