Hostname: page-component-76fb5796d-5g6vh Total loading time: 0 Render date: 2024-04-30T05:15:32.668Z Has data issue: false hasContentIssue false
  • English
  • Français

Biocatalytic Synthesis of Polyesters by Enzyme-Catalyzed Transesterification in Organic Media

Published online by Cambridge University Press:  21 February 2011

Cary J. Morrow ,
J. Shield Wallace ,
Gregory M. Bybee ,
Kristin B. Reda  and
Mark E. Williams
Cary J. Morrow
Affiliation:
University of New Mexico, Department of Chemistry, Albuquerque, NM 87131
J. Shield Wallace
Affiliation:
University of New Mexico, Department of Chemistry, Albuquerque, NM 87131
Gregory M. Bybee
Affiliation:
University of New Mexico, Department of Chemistry, Albuquerque, NM 87131
Kristin B. Reda
Affiliation:
University of New Mexico, Department of Chemistry, Albuquerque, NM 87131
Mark E. Williams
Affiliation:
University of New Mexico, Department of Chemistry, Albuquerque, NM 87131
Get access

Abstract

Enzyme-catalyzed preparation of polymers offers several potentially valuable advantages over the usual polymerization procedures. This paper summarizes our successful use of lipase-catalyzed polycondensations to prepare both a series of achiral [AA-BBJx polyesters from simple bis(2,2,2- trichloroethyl) alkanedioates and diols and of an optically active, epoxy-substituted polyester having a stereochemical purity estimated to be greater than 96%, from racemic bis(2,2,2-trichloroethyl) trans- 3,4-epoxyhexanedioate and 1,4-butanediol. The somewhat less successful polycondensation of a series of A-B monomers is also described. All of the reactions were carried out at ambient temperature in anhydrous, low to intermediate polarity, organic solvents such as ether, THF, and methylene choride, using porcine pancreatic lipase (PPL) as the catalyst. Possible explanations for the difference between the A-B and AA + BB cases, based on NMR analysis of the reactions' progress are considered.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 174: Symposium R – Materials Synthesis Utilizing Biological Processes , 1989 , 197
Copyright
Copyright © Materials Research Society 1990

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

1. Klibanov, A. M., CHEMTECH, 354 (1986).Google Scholar
2. For a comprehensive list of references, see Morrow, C. J. and Wallace, J. S. in Biocatalysis, edited by Abramowicz, D. A. (Van Nostrand Reinhold, New York, 1990) in press.Google Scholar
3. Okumura, S., Iwai, M., and Tominaga, Y., Agric. Biol. Chem., 48, 2805 (1984).Google Scholar
4. Margolin, A. L., Crenne, J.-Y., and Klibanov, A. M., Tetrahedron Lett., 28, 1607 (1987).Google Scholar
5. Ajima, A., Yoshimoto, T., Takahashi, K., Tamara, Y., Saito, Y., and Inada, Y., Biotechnology Lett., 7, 303 (1985).Google Scholar
6. Matsumura, S. and Takahashi, J., Makromol. Chem. Rapid Commun, 7, 369 (1986).Google Scholar
7. Kitazume, T., Sato, T., and Kobayashi, T., Chem. Express, 3, 135 (1988).Google Scholar
8. Gutman, A. L., Oren, D., Boltanski, A., and Bravdo, T., Tetrahedron Lett., 28, 5367 (1987).Google Scholar
9. Gutman, A. L. and Bravdo, T., J. Org. Chem., 54, 5645 (1989).Google Scholar
10. Abramowicz, D. A. and Keese, C. R., Biotechnology and Bioengineering, 33, 149 (1989).Google Scholar
11. Wallace, J. S. and Morrow, C. J., J. Polym. Sci. Part A: Polym. Chem., 27, 3271 (1989).Google Scholar
12. Zumstein, F., Koenigsberger, R., and Zumstein, F. Jr, German Patent 2,342,673 to Ono Pharmaceutical Co., Ltd, Osaka (1974).Google Scholar
13. Selegny, E., Ed., Optically Active Polymers (Reidel, D. Publishing Co., Dordrecht, Holland, 1979).Google Scholar
14. Vogl, O. and Jaycox, G. D., CHEMTECH, 683 (1986).Google Scholar
15. Wallace, J. S. and Morrow, C. J., J. Polym. Sci. Part A: Polym. Chem., 27, 2553 (1989).Google Scholar
16. Hassner, A. and Alexanian, V., Tetrahedron Lett., 4475 (1978).Google Scholar
17. Dahill, R. T., Dorsky, J., and Easter, W., J. Org. Chem., 35, 251 (1970).Google Scholar
18. Whitesides, G. M. and Lewis, D. W., J. Am. Chem. Soc., 92, 6979 (1970).Google Scholar