Skip to main content

The Use of Immobilized Penicillin G Acylase in Organic Synthesis

  • Chapter
Microbial Reagents in Organic Synthesis

Part of the book series: NATO ASI Series ((ASIC,volume 381))

Abstract

Non conventional applications of immobilized Penicillin G acylase with respect to its chemoselectivity and stereoselectivity are examined.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Nayler, J.H.C. (1991) ‘Semi-synthetic approaches to novel penicillins’, TIBS 16, 234–237 and references therein.

    CAS  Google Scholar 

  2. Savidge, T. A. (1984) ‘Enzymatic conversions used in the production of penicillins and cephalosporins’, in E. J. Vandamme (ed), ‘Biotechnology of Industrial Antibiotics’, Marcel Dekker Co, New York, pp. 171–224.

    Google Scholar 

  3. Valle, F., Balbas, P., Merino, E. and Bolivar F. (1991) ‘The role of penicillin amidases in nature and in industry’, TIBS 16, 36–40.

    CAS  Google Scholar 

  4. Schumacher, G., Sizmann, D., Haug, H. Buckel, P. and Böck, A. (1986) ‘Penicillin acylase from E. coli: unique gene-protein relation’ Nucleic Acids Res. 14, 5713–5727.

    Article  CAS  Google Scholar 

  5. Daumy, G. O., Danley, D. and McColl, A. S. (1985) ‘Role of protein subunits in Proteus rettgeri Penicillin G acylase’, J. of Bacteriol. 163, 1279–1281.

    CAS  Google Scholar 

  6. Baldaro, E. M. (1991) ‘Effect of temperature on enzymatic synthesis of cephalosporins’, in Pandit, U. K. and Alderweireldt, F. C. (eds) ‘Bioorganic chemistry in healthcare and technology’, Plenum Press, New York, pp. 237–240.

    Chapter  Google Scholar 

  7. Zmijeski, M. J., Briggs, B. S., Thompson, A. R., Wright, I. G. (1991) ‘Enantioselective acylation of a β-lactam intermediate in the synthesis of Loracarbef using Penicillin G amidase’ Tetrahedron Lett. 32, 1621–1622.

    Article  Google Scholar 

  8. Waldmann, H. (1991) ‘Enzymatic protecting group techniques’, Kontakte 2, 33–54.

    Google Scholar 

  9. Didziapetris, R., Drabnig, B., Schellenberger, V., Jakubke, H.-D. and Svedas, V. (1991) ‘Penicillin acylase-catalysed deprotection of amino groups as a promising approach in enzymatic peptide synthesis’, FEBS lett. 287, 31–33.

    Article  CAS  Google Scholar 

  10. Hermann, P. (1991) ‘Enzymatic manipulation of protecting groups: more than deprotection’ Biomed. Biochim. Acta 50, 19–31.

    Google Scholar 

  11. Fuganti, C., Grasselli, P. and Casati, P. (1986) ‘Immobilized Penicillinacylase: application to the synthesis of the dipeptide Aspartame’, Tetrahedron Lett. 27, 3191–3194.

    Article  CAS  Google Scholar 

  12. Recently this concept has been applied to the entirely enzymatic synthesis of aspartame: Stoineva, I.B., Galunsky, B.P., Lozanov, S.V., Ivanov, I.P. and Petkov, D.D. (1992) ‘Enzymic synthesis design and enzymic synthesis of Aspartame’ Tetrahedron, 48, 115–1122

    Article  Google Scholar 

  13. Crout, D.H.G., Christen, M. (1989) ‘Biotransformations in organic synthesis’in R. Scheffold ed., Modern synthetic methods vol. 5, pp 1–114, Springer Verlag, Berlin

    Chapter  Google Scholar 

  14. Boland, W., Froessl, C., Lorenz, M. (1991) ‘Esterolytic and lipolytic enzymes in organic synthesis’ Synthesis, 1049–1072.

    Google Scholar 

  15. Cooper, R. D. G. and Spry, D. O. (1972) ‘Rearrangements of cephalosporins and penicillins’, in Flynn, E.H. (ed.) ‘Cephalosporins and penicillins’, Academic Press, New York, pp. 183–254.

    Google Scholar 

  16. Baldaro, E., Faiardi, D., Fuganti, C., Grasselli, P., Lazzarini, A. (1988) ‘Phenylacetyloxymethylene, a carboxyl protecting group removable with immobilized Penicillin Acylase, useful in benzyl penicillin chemistry’, Tetrahedron Lett. 29, 4623–4624.

    Article  CAS  Google Scholar 

  17. Cole, M. (1964) ‘Properties of the Penicillin Deacylase Enzyme of Escherichia coli’, Nature 203, 519–520.

    Article  CAS  Google Scholar 

  18. Rossi, D., Romeo, A., Lucente, G. (1978) ‘Approach to the use of benzylpenicillinacylase for configurational correlations of amino compounds’, J. Org. Chem., 43, 2576–2581.

    Article  CAS  Google Scholar 

  19. Rossi, D., Calcagni, A., Romeo, A. (1979) ‘Approach to the use of benzylpenicillinacylase for configurational correlations of amino compounds. Hydrolysis of N-(p-aminophenylacetyl)derivatives of some chiral primary amines’, J. Org. Chem. 44, 2222–2225.

    Article  CAS  Google Scholar 

  20. Pessina, A., Lüthi, P. and Luisi, P. L. (1988) ‘Amide-bond synthesis catalyzed by Penicillin acylase’, Helv. Chim. Acta 71, 631–641.

    Article  CAS  Google Scholar 

  21. Waldmann, H. (1989) ‘A new access to chiral 2-furylcarbinols by enantioselective hydrolysis with penicillin acylase’, Tetrahedron Lett. 30, 3057–3058.

    Article  CAS  Google Scholar 

  22. Fuganti, C., Rosell, M.C., Rigoni, R., Servi, S., Tagliani, A., Terreni, M. unpublished results

    Google Scholar 

  23. For examples of enzyme catalysed preparation of this compound see for instance: Kim, M.-J., Kim, J.Y. (1991) ‘Synthesis of optically pure (R)-2-hydroxy acids using D-lactate dehydrogenase’ J. Chem. Soc Chem. Commun. 326–327.

    Google Scholar 

  24. Sugai, T., Ohta, H. (1991) ‘A simple preparation of (R)-2-hydroxy-4-phenyl butanoic acid’ Agric. Biol. Chem. 55, 293–294

    Article  CAS  Google Scholar 

  25. Martin, J. F. and Liras, P. (1989) ‘Enzymes involved in penicillin, cephalosporin and cephamycin biosynthesis’, Adv. Biochem. Engineer. Biotechnol. 39, 153–187.

    Article  CAS  Google Scholar 

  26. Fuganti, C., Grasselli, P., Seneci, P. F., Servi, S. and Casati, P. (1986) ‘Immobilized benzylpenicillin acylase: application to the synthesis of optically active forms of carnitine and propranolol’, Tetrahedron Lett. 27, 2061–2062.

    Article  CAS  Google Scholar 

  27. Fuganti, C., Grasselli, P., Servi, S., Lazzarini, A. and Casati, P.(1988) ‘Substrate specificity and enantioselectivity of penicillinacylase catalysed hydrolysis of phenacetyl esters of synthetically useful carbinols’ Tetrahedron 44, 2575–2582.

    Article  CAS  Google Scholar 

  28. Fuganti, C., Grasselli, P., Servi, S., Lazzarini, A. and Casati, P. (1987) ‘Penicillinacylase and α-chymotripsin catalysed hydrolysis of phenylacetate and phenylpropionate esters of 2,2-dimethyl-l,3-dioxolane-4-methanols’ J. Chem. Soc., Chem. Commun. 538–539.

    Google Scholar 

  29. Fuganti, C., Rosell, C. M., Servi, S., Tagliani, A., Terreni, M. (1992) ‘Enantioselective recognition of the phenacetyl moiety in the pen G acylase catalysed hydrolysis of phenylacetate esters’, Tetrahedron: Asym. 3, 383–386.

    Article  CAS  Google Scholar 

  30. Fuganti, C., Rosell, M.C., Rigoni, R., Servi, S., Tagliani, A., Terreni, M. (1992) ‘Penicillin acylase mediated synthesis of formyl cephamandole’, Submitted for publication

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1992 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Baldaro, E., Fuganti, C., Servi, S., Tagliani, A., Terreni, M. (1992). The Use of Immobilized Penicillin G Acylase in Organic Synthesis. In: Servi, S. (eds) Microbial Reagents in Organic Synthesis. NATO ASI Series, vol 381. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-2444-7_14

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-2444-7_14

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-5078-4

  • Online ISBN: 978-94-011-2444-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics