Skip to main content
SpringerLink
Log in
Book cover

Microbial Reagents in Organic Synthesis pp 199–208Cite as

Enzymatic Aminolysis, Hydrazinolysis and Oximolysis Reactions

  • Chapter

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

Abstract

Lipases successfully catalyze aminolysis reactions using both activated or non-activated esters; the corresponding amides are obtained in high optical yields. These enzymes and, especially lipase from Pseudomonas cepacia, are excellent biocatalysts in the hydrazinolysis reaction; the best nucleophiles in this process are hydrazines with electronwithdrawing groups with which it is possible to obtain Naminosuccinimide derivatives from dimethyl succinate. The lipase catalyzed oximolysis reaction is a very efficient method to prepare oxime esters and oxime tert-butylcarbonates from oximes and vinyl esters and tert-butylpyrocarbonates respectively.

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

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

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Klibanov, Alexander M. (1990) “Asymmetric Transformations Catalyzed by Enzymes in Organic Solvents”, Acc. Chem. Res., 23, 114–120.

    Article  CAS  Google Scholar 

  2. Drueckhammer, Dale G., Hennen, William J., Pederson, Richard L., Barbas Carlos F., Gautheron, Christine M., Krach, T. and Wong, C-H. (1991) “Enzyme Catalysis in Synthetic Carbohydrate Chemistry”, Synthesis, 499–525.

    Google Scholar 

  3. Boland, W., Frössl, Ch. and Lorent, M. (1991) “Esterolytic and Lipolytic Enzymes in Organic Synthesis”, Synthesis, 1049–1072.

    Google Scholar 

  4. Brieva, R. (1991) “Synthesis of Chiral Nitrogen Compounds Using Enzymes in Organic Solvents”, Doctoral Thesis, Oviedo University, Spain.

    Google Scholar 

  5. Zaks, A. and Klibanov, Alexander M. (1985) “Enzyme-Catalyzed Processes in Organic Solvents”, Proc. Natl. Acad. Sci. USA, 82, 3192–3196.

    Article  CAS  Google Scholar 

  6. Klibanov, Alexander M. (1986) “Enzymes that work in Organic Solvents”, CHEMTECH, 354–359.

    Google Scholar 

  7. Margolin, Alexey L. and Klibanov, Alexander M. (1987) “Peptide Synthesis Catalyzed by Lipases in Anhydrous Organic Solvents”, J. Am. Chem. Soc., 109, 3802–3804.

    Article  CAS  Google Scholar 

  8. Blair West, J. and Wong, C-H. (1987) “Use of Nonproteases in Peptide Synthesis”, Tetrahedron Lett., 28, 1629–1632.

    Article  Google Scholar 

  9. Margolin, Alexey L., Tai, D-F. and Klibanov, Alexander M. (1987) “Incorporation of D-Aminoacids into Peptides via Enzymatic Condensation in Organic Solvents”, J. Am. Chem. Soc., 109, 7885–7887.

    Article  CAS  Google Scholar 

  10. Gotor, V., Brieva, R. and Rebolledo, F. (1988) “A Simple Procedure for the Preparation of Chiral Amides”, Tetrahedron Lett., 29, 6973–6914.

    Article  CAS  Google Scholar 

  11. Kirchner, G., Scollar, Mark P. and Klibanov, Alexander M. (1985) “Resolution of Racemic Mixtures via Lipase Catalysis in Organic Solvents”, J. Am. Chem. Soc., 107, 7072–7076.

    Article  CAS  Google Scholar 

  12. Gotor, V., Brieva, R., Gonzalez, C. and Rebolledo, F. (1991) “Enzymatic Aminolysis and Transamidation Reactions”, Tetrahedron, 47, 9207–9214.

    Article  CAS  Google Scholar 

  13. Engel, K-H. (1991) “Enantioselective Esterification of 2-Methylalkanoic Acids”, Tetrahedron: Asymmetry, 2, 165–168.

    Article  CAS  Google Scholar 

  14. Garcia, M-J., Brieva, R., Rebolledo, F. and Gotor, V. (1991) “Enzymatic Hydrolysis of 2,2,2-Trifluoroethyl-α-Chloro- α -Phenylacetate in Organic Media”, Biotechnol. Lett., 13, 867–870.

    Article  CAS  Google Scholar 

  15. Kitaguchi, K., Fitzpatric, Paul A., Huber, Joel E. and Klibanov, Alexander M. (1989) “Enzymatic Resolution of Racemic Amines: Crucial Role of the Solvent”, J. Am. Chem. Soc., 111, 3094–3095.

    Article  CAS  Google Scholar 

  16. Brieva, R., Rebolledo, F. and Gotor, V. (1990) “Enzymatic Synthesis of Amides with two Chiral Centers”, J. Chem. Soc., Chem. Commun., 1386–1387.

    Google Scholar 

  17. Gotor, V., Garcia, M-J. and Rebolledo, F. (1990) “An Enzymatic Method for the Preparation of Chiral Diamides”, Tetrahedron: Assymmetry, 1, 277–278.

    Article  CAS  Google Scholar 

  18. Rebolledo, F., Brieva, R. and Gotor, V. (1989) “Enzymatic Synthesis of Propargylamides”, Tetrahedron Lett., 30, 5345–5346.

    Article  CAS  Google Scholar 

  19. Francalanci, F., Cesti, P., Cabri, W., Bianchi, D., Martinengo, T. and Foà, M. (1987) “Lipase-Catalyzed Resolution of Chiral 2-Amino-l-Alcohols”, J. Org. Chem., 52, 5079–5082.

    Article  CAS  Google Scholar 

  20. Gotor, V., Brieva, R. and Rebolledo, F. (1988) “Enzymatic Acylation of Amino Alcohols by Porcine Pancreatic Lipase”, J. Chem. Soc., Chem. Commun., 957–958.

    Google Scholar 

  21. Kramer, U., Guggisberg, A., Hesse, M. and Schmid, H. (1977) “The Zip Reaction: A New Method for Ring Expansion; Synthesis of 17- and 21-Membered Polyaminolactams”, Angew. Chem. Int. Ed. Engl., 16, 861–862.

    Article  Google Scholar 

  22. Tuccio, B., Ferré, E. and Comeau, L. (1991) “Lipase-Catalyzed Synthesis of N-Octyl -Alkylamides in Organic Media”, Tetrahedron Lett., 32, 2763–2764.

    Article  CAS  Google Scholar 

  23. Djeghaba, Z., Delueze, H., De Jeso, B., Messadi, D. and Maillard, B. (1991) “Enzymes in Organic Synthesis VII: Enzymatic Acylation of Amine Tetrahedron Lett., 32, 761–762.

    Article  CAS  Google Scholar 

  24. Gotor, V., Astorga, C. and Rebolledo, F. (1990) “An Improved Method for the Preparation of Acylhydrazines: The First Example of an Enzymatic Hydrazinolysis Reaction”, Synlett, 387–388.

    Google Scholar 

  25. Astorga, C., Rebolledo, F. and Gotor, V. (1991) “Synthesis of Hydrazides Trough an Enzymatic Hydrazinolysis Reaction”, Synthesis, 350–352.

    Google Scholar 

  26. Astorga, C., Rebolledo, F. and Gotor, V. (1992) “Enzymatic Hydrazinolysis of Diesters and Synthesis of N-Aminosuccinimide Derivatives”, Synthesis, in press.

    Google Scholar 

  27. Kornet, Michael J. (1984) “Synthesis and Anticonvulsant Evaluation of N-Aminosuccinimides”, J. Pharm. Sci., 73, 405–406.

    Article  CAS  Google Scholar 

  28. Gotor, V. and Menendez, E. (1990) “Synthesis of Oxime Esters Trough an Enzymatic Oximolysis Reaction”, Synlett, 699–700.

    Google Scholar 

  29. Itoh, M., Hagiwara, D. and Kamiya, T. (1977) “Peptides VI. Some Oxime Carbonates as Novel t-Butoxycarbonylating Reagents”, Bull. Chem. Soc. Jpn., 50, 718–721.

    Article  CAS  Google Scholar 

  30. Menendez, E. and Gotor, V. “Acylation and Alkoxycarbonilation of Oximes through an Enzymatic Oximolysis Reaction”, submitted for publication.

    Google Scholar 

  31. Ghogare, A. and Kumar, S. (1989) “Oxime Esters as Novel Irreversible Acyl Trnsfer Agents for Lipase Catalysis in Organic Solvents”, J. Chem. Soc. Chem. Commun., 1533–1535.

    Google Scholar 

  32. Goghare, A. and Kumar S. (1990) “Novel Route to Chiral Polymers Involving Biocatalytic Transesterification of O-Acryloil Oximes”, J. Chem. Soc. Chem. Commun, 134–135.

    Google Scholar 

  33. Gotor, V. and Pulido, R. (1991) “An Improved Procedure for Regioselective Acylation of Carbohydrates: Novel Enzymatic Acylation of α-D-Glucopyranose and Methyl α-Glucopyranoside”, J. Chem. Soc. Perkin Trans. I, 491–492.

    Article  Google Scholar 

  34. Gotor, V. and Moris, F. (1992) “Regioselective Acylation of 2′-Deoxynucleosides Through an Enzymatic Reaction with Oxime Esters”, Synthesis, in press.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Departamento de Química Orgánica e Inorgánica Facultad de Química, Universidad de Oviedo, 33071, Oviedo, Spain

    V. Gotor

Authors
  1. V. Gotor
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Dipartimento di Chimica, Politecnico di Milano, Milano, Italy

    Stefano Servi

Rights and permissions

Reprints and permissions

Copyright information

© 1992 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Gotor, V. (1992). Enzymatic Aminolysis, Hydrazinolysis and Oximolysis Reactions. 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_16

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-2444-7_16

  • 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

Search

Navigation