Summary
In the esterification of 2-phenoxypropionic acids catalyzed byCandida cylindracea lipase, its enantio-selectivity was inverted in non-polar solvents such as carbon tetrachloride from that in polar solvents such as acetone. A model for this inversion is suggested.
Similar content being viewed by others
References
Chen, C. and Sih, C. J. (1989). Angew. Chem. Int. Ed.28, 695.
Dordick, J. S. (1989). Enzyme Microb. Technol.11, 194.
Francalanci, F., Cesti, P., Cabri, W., Bianchi, D., Martinengo, T., and Foa, M. (1987). J. Org. Chem.52, 5079.
Inagaki, T. and Ueda, H. (1987). Agric. Biol. Chem.51, 1345.
Kirchner, G., Scollar, M. P., and Klibanov, A. M. (1985). J. Am. Chem. Soc.107, 7072.
Kitaguchi, H., Itoh, I., and Ono, M. (1990). Chemistry Lett. 1203.
Klibanov, A. M. (1989). Trends Biochem. Soc.14, 141.
Klibanov, A. M. (1990). Acc. Chem. Res.23, 114.
Parida, S. and Dordick, J. S. (1991). J. Am. Chem. Soc.113, 2253.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Ueji, S., Fujino, R., Ōkubo, N. et al. Solvent-induced inversion of enantiosflectivity in lipase-catalyzed esterification of 2-phenoxypropionic acids. Biotechnol Lett 14, 163–168 (1992). https://doi.org/10.1007/BF01023352
Issue Date:
DOI: https://doi.org/10.1007/BF01023352