Abstract
Trimethyl and triethyl esters of tricarballylic acid and citric acid were hydrolysed with porcine liver esterase(PLE) to the isomeric diesters. In all cases the hydrolysis took place with poor regioselectivity (maximum 50% excess). However, the hydrolysis of trimethyl and triethyl esters of tricarballylic acid and of the triethyl ester of citric acid with subtilisin was absolutely regioselective and the symmetric 1,5-diester was obtained.
Similar content being viewed by others
References
Breusch, F.L., and Pelister, Y. (1972).Fette, Seifen, Anstrichmittel 74, 321–324.
Francis, J.C., and Jones, J.B. (1984).J. Chem. Soc. Chem. Commun. 579–580.
Huang, F.-C., Hsei Lee, L.F., Mittal, R.S.D., Ravikumar, P.R., Amigo Chan, J., and Sih, J.C. (1975).J. Am. Chem. Soc. 75, 4144–4145.
Jones, J.B. (1986).Tetrahedron 42, 3351–3403.
Lam, L.K.P., Hui, R.A.H., and Jones, J.B. (1986).J. Org. Chem. 51, 2047–2050.
Turner, N.J. (1989).Natural Products Reports 625-644.
Wong, C.-H. (1989).Science 244, 1145–1152.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kvittingen, L., Partali, V., Brænden, J.U. et al. Highly regioselective hydrolysis of tricarballylates (“retro-fats”) and citrates by subtilisin. Biotechnol Lett 13, 13–18 (1991). https://doi.org/10.1007/BF01033509
Issue Date:
DOI: https://doi.org/10.1007/BF01033509