Drastic enhancement of the enantioselectivity of lipase-catalysed esterification in organic solvents by the addition of metal ions

Abstract

By the addition of metal ion-containing water, a marked enhancement of the enantioselectivity for the lipase-catalysed esterification of 2-(4-substituted-phenoxy)propionic acids in Prⁱ₂O was observed, the mechanism of which will be discussed briefly on the basis of the initial rate obtained for each enantiomer of the substrate.

References

1. Bernardo Herradon, J. Org. Chem., 1994, 59, 2891; E. Santaniello, P. Ferraboschi, P. Grisenti and A. Manzocchi, Chem. Rev., 1992, 92, 1071; A. M. Klibanov, Acc. Chem. Res., 1990, 23, 114.
2. D. T. Witiak, C.-L. Ho, R. E. Hackney and W. E. Coner, J. Med. Chem., 1968, 11, 1086.
3. C.-S. Chen, Y. Fujimoto, G. Girdankas and C. J. Sih, J. Am. Chem. Soc., 1982, 104, 7294.
4. Y. Yasufuku and S. Ueji, Bioorg. Chem., 1997, 25, 88.
5. H. Kitaguchi, I. Toh and M. Ono, Chem. Lett., 1990, 1203.
6. P. A. Buruke, R. G. Griffin and A. M. Klibanov, Biotechnol. Bioeng., 1993, 42, 87.