Abstract
Acid anhydrides were used as highly reactive and non-water-producing acyl donors for hydrolase-catalyzed enantioselective esterification. Efficient kinetic resolution of dl-menthol has been achieved via lipase-catalyzed enantioselective esterification in cyclohexane when propionic anhydride as an acyl donor was continuously fed into a reactor containing dl-menthol and Candida cylindracea lipase OF 360, while a high concentration of the acid anhydride in a batch reaction system with a dehydrated organic solvent did not facilitate the reaction, because water necessary for the enzyme function was consumed by the competing hydrolysis of the anhydride catalyzed by the same enzyme. The efficiency of this fed-batch reaction system using acid anhydride was higher and the enzyme stability in repeated use was much better than those of conventional batch and fed-batch reaction systems using propionic acid as an acyl donor. The optical purity (more than 98% e.e.) of the l-menthyl ester produced in the fed-batch system using the anhydride was comparable to that in the system using the corresponding acid. *** DIRECT SUPPORT *** AG903062 00002
Similar content being viewed by others
References
Berger B, Raliller CG, Konigsberger K, Faber K, Griengl H (1990) Enzymatic acylation using acid anhydrides: crucial remove of acid. Tetrahedron [Asymmetry] 1:541–546
Bianchi D, Cesti P, Battistel E (1988) Anhydrides as acylating agents in lipase-catalyzed stereoselective esterification of racemic alcohols. J Org Chem 53:5531–5534
Chen C-S, Sih CJ (1989) General aspects and optimization of enantioselective biocatalysis in organic solvents: the use of lipase. Angew Chem Int Ed Engl 28:695–707
Fukusaki E, Senda S, Nakazono Y, Yuasa H, Omata T (1992) Lipase-catalyzed kinetic resolution of 2,3-epoxy-8-methyl-1-nonanol, the key intermediate in the synthesis of the gypsy moth pheromone. J Ferment Bioeng 73:280–283
Gutman AL, Brenner D, Boltanski A (1993) Convenient practical resolution of racemic alkyl-aryl alcohols via enzymatic acylation with succinic anhydride in organic solvents. Tetrahedron [Asymmetry] 4:839–844
Klibanov AM (1990) Asymmetric transformations catalyzed by enzymes in organic solvents. Acc Chem Res 23:114–120
Koshiro S, Sonomoto K, Tanaka A, Fukui S (1985) Stereoselective esterification of dl-menthol by polyurethane-entrapped lipase in organic solvent. J Biotechnol 2:47–57
Margolin AL (1993) Enzymes in the synthesis of chiral drugs. Enzyme Microb Technol 15:266–280
Tanaka A, Sonomoto K (1990) Immobilized biocatalysts in organic solvents. Chemtech February:112–117
Xie Z-F (1991) Pseudomonas fluorescens lipase in asymmetric synthesis. Tetrahedron [Asymmetry] 2:733–750
Zaks A, Klibanov AM (1988) The effect of water on enzyme action in organic media. J Biol Chem 263:8017–8021
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Xu, J.H., Kawamoto, T. & Tanaka, A. Efficient kinetic resolution of dl-menthol by lipase-catalyzed enantioselective esterification with acid anhydride in fed-batch reactor. Appl Microbiol Biotechnol 43, 402–407 (1995). https://doi.org/10.1007/BF00218440
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00218440