Abstract
Of 25 commercial lipases, nine were able to catalyse the hydrolysis of ethyl D,L-2-amino-4-phenylbutyrate (D,L-APBAE) to optically active D-APBAE, an intermediate for the synthesis of inhibitors of angiotensin-converting enzyme, with specific selectivity ranging between 3.7 and 12.5. Optimal conditions for porcine pancrease lipase-catalyzed reaction gave a 68% conversion and the D-ester was obtained by a simple extraction with an optical purity of 98%. Saponification of the ethyl ester of D-APBA in 1 M NaOH gave the optically active D-APBA with a chemical purity greater than 99%.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Chen, C.S., Fujimoto, Y., Girdaukas, G. and Sih, C.J. (1982). J. Am. Chem. Soc., 104: 7294–7299.
Chen, S.T., Chen, S.Y., Hsiao, S.C. and Wang, K.T. (1991). Biotechnol. Lett., 13: 773–778.
Chen, S.T., Hsiao, S.C., Chiou, A.J., Wu, S.H. and Wang, K.T. (1992). J. Chin. Chem. Soc., 39: 91–99.
Fraser, J.L., Jackson, R.F.W. and Porter, B. (1994) Synlett, 5: 379–380.
Kijima, T., Ohshima, K. and Kise, H. (1994).J. Chem. Tech. Biotechnol., 59: 61–65.
Pearson, A J. and Lee K. S., (1994). J. Org. Chem., 59: 2304–2313.
Wong, C.H., Chen, S.T., Hennen, W.J., Bibbs, J.A., Wang, Y.F., Liu, J.L.-C, Pantoliano, M.W., Whitlow, M. and Bryan, P.N. (1990). J. Am. Chem Soc., 112: 945–953.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Houng, JY., Hsieh, CL. & Chen, ST. Lipase-catalysed kinetic resolution of ethyl D,L-2-amino-4-phenylbutyrate by hydrolysis. Biotechnol Tech 10, 353–358 (1996). https://doi.org/10.1007/BF00173254
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00173254