Abstract
Porcine pancreatic lipase can catalyze transesterification reac tions in organic solvents in a highly regioselective manner. Lipase powder was suspended in solutions of various diols in ethyl carboxylates, and the mixtures were shaken at 30°C; as a result, pri mary monoesters of glycols were produced on a preparative scale.
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References
Mellan, I. (1962),Polyhydric Alcohols, Spartan Books, Washington DC.
Benson, F. R. (1967), inNon-Ionic Surfactants, Schick, M. J., ed., Dekker, New York.
Masamune, S., and Choy W. (1982),Aldrichimica Acta 15, 47.
von Bremer, P., Davis, J.H. (1980), inKirk-Othmer Encyclopedia of Chem ical Technology, Wiley, New York, vol. 11, p. 966.
Goldsmith, H. A. (1943),Chem. Rev. 33, 257.
Markly, K. S. (1961), inFatty Acids, 2nd ed., Markly, K. S., ed., Interscience, New York, Part 2, Chap. 9.
Bartok, M., Kozma, B., and Apjok, J. (1964),Izv. Acad. Nauk SSSR, Ser. Khim., 2192.
Mattson, F. H. and Volpenheim, R. A. (1962),J. Lipid Res. 3, 281.
Notheisz, F., Bartok, M., and Remport, V. (1972),Acta Phys. Chem. 18, 89.
nBuchnea, D., inFatty Acids and Glycerides, Kuksis, A., ed., Plenum, New York, vol. 1, Chap. 5.
Decouzon, M, and Naudet, M. (1966),Bull. Soc. Chim. Fr. 3541.
Johnson, A. W., Long, A. G., and Dalgliesh, C. E. (1951), inChemistry of Carbon Compounds, Rodd, E. H., ed., Elsevier, Amsterdam, Vol. 1, Part A, p. 649.
Mitsunobu, O., Kimura, J., Iiizumi, K., and Yanagida, N. (1976),Bull. Chem. Soc. Japan 49, 510.
Mukaiyama, T., Pai, F.-C., Onaka, M., and Narasaka, K. (1980),Chem. Lett. 563.
Posner, G. H. and Oda, M. (1981),Tetrahedron Lett. 22, 5003.
Mitsunobu, O. (1981),Synthesis 1.
Sekine, M., Kume, A., and Hata, T. (1981),Tetrahedron Lett. 22, 3617.
Mistrik, E. J. and Mateides, A. (1983),Chem. Technol. (Leipzig) 35, 90.
Jones, J. B., Perlman, D., and Sih, C. J., (1976), eds.Applications of Biochemi cal Systems in Organic Chemistry, Wiley, New York.
Klibanov, A. M. (1983),Science,219, 722.
Whitesides, G. M. and Wong, C.-H. (1983),Aldrichimica Acta 16, 27.
Zaks, A., and Klibanov, A. M. (1984),Science,224, 1249.
Brockerhoff, H. and Jensen, R. G. (1974),Lipolytic Enzymes, Academic Press, New York.
Lavayre, J., Verrier, J., and Baratti, J. (1982),Biotechnol. Bioeng. 24, 2175.
Ladner, W. E. and Whitesides, G. M. (1984),J. Am. Chem. Soc. 106, 7250.
Cambou, B., and Klibanov, A. M. (1984),J. Am. Chem. Soc. 106, 2687.
Cambou, B., and Klibanov, A. M. (1984),Biotechnol. Bioeng. 26, 1449.
Zaks, A., and Klibanov, A. M. (1985),Proc. Natl. Acad. Sci. USA,82, 3192.
Ellman, C. L. (1951),Arch. Biochem. Biophys. 82, 70.
Koskikallio, J. (1969), inThe Chemistry of Carboxylic Acids and Esters, Patai, S., ed., Interscience, London, Chap. 3.
Inada, Y., Nishimura, H., Takahashi, K., Yoshimoto, T., Saha, A. R., and Saito, Y. (1984),Biochem. Biophys. Res. Commun. 122, 845.
Yoshimoto, T., Takahashi, K., Nishimura, H., Ajima, A., Tamaura, Y., and Inada, Y. (1984),Biotechnol. Lett. 6, 337.
Takahashi, K., Nishimura, H., Yoshimoto, T., Okada, M., Ajima, A., Matsushima, A., Tamaura, Y., Saito, Y., and Inada, Y. (1984),Biotechnol. Lett. 6, 765.
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Cesti, P., Zaks, A. & Klibanov, A.M. Preparative regioselective acylation of glycols by enzymatic transesterification in organic solvents. Appl Biochem Biotechnol 11, 401–407 (1985). https://doi.org/10.1007/BF02798673
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DOI: https://doi.org/10.1007/BF02798673
Index Entries
- Preparative acylation of glycols, by enzymatic transesterification
- acylation of glycols, by enzymatic transesterification
- glycols, acylation by enzymatic transesterification of
- enzymatic transesterification, in the preparative acylation of glycols
- regioselective acylation, of glycols by enzymatic transesterification
- transesterification, of glycols, enzyme-catalyzed