Enzymatic synthesis of (R) and (S) 1-deuterohexanol
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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 andPseudomonas 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 regeneratedin 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.
KeywordsAlcohol Dehydrogenase Ethyl Ether Hexanol Biphasic System Hexane Layer
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- 4.Bradshaw, C. W., Shen, G.-J., and Wong, C.-H. (1991),Bioorg. Chem. in press.Google Scholar
- 5.Shen, G.-J., Wang, Y. F., Bradshaw, C., and Wong, C.-H. (1990),J. Chem. Soc. Chem. Commun. 677; Bradshaw, C. W., Fu, H., Shen, G.-J., and Wong, C.-H.J. Org. Chem. in press.Google Scholar
- 6.Bradshaw, C. W., Hummel, W., and Wong, C.-H.J. Org. Chem. in press.Google Scholar
- 12.Takano, S., Hatakeyama, S., and Ogawasara, K. (1977),J. Chem. Soc. Chem. Commun. 68.Google Scholar
- 14.Dalziel, K. and Dickinson, F. M. (1966),Biochem. J. 100, 491.Google Scholar