Skip to main content
SpringerLink
Log in

Novel biocatalytic process of N-substituted acrylamide synthesis

  • Producers, Biology, Selection, and Genetic Engineering
  • Published:
Applied Biochemistry and Microbiology Aims and scope Submit manuscript

Abstract

The enzymatic synthesis of N-substituted acrylamides (N-isopropyl acrylamide and N, N-dimethylaminopropyl acrylamide) was demonstrated for the first time. The Rhodococcus erythropolis 37 strain, exhibiting acylamidase activity, was used as a source of enzyme, and water-dissolved acrylamide and isopropylamine/dimethylaminopropylamine served as substrates. The optimum conditions for the synthesis of acrylamide N-substitutes were determined using N-isopropyl acrylamide. The yield of the product was maximum at pH 9.5–10.5, substrate (acrylamide/isopropylamine) ratio within the range from 1.3: 1 to 2: 1, and absolute substrate concentrations of 8.0 (acrylamide) and 4.0% (isopropylamine). These conditions allowed for the synthesis of 22 g/L of N-isopropyl acrylamide.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

AA:

acrylamide

GC:

gas chromatography

DIMAPA:

N,N-dimethylaminopropyl acrylamide

IPA:

isopropylamine

IPAA:

N-isopropyl acrylamide

AAC:

acrylic acid

St:

acetamide (standard)

References

  1. Abramova, L.I., Baiburdov, T.A., Grigoryan, E.P., Zil’berman, E.N., and Kurenkov, V.F., Poliakrilamid (Polyacrylamide), Kurenkov, V.F., Ed., Moscow: Khimiya, 1992.

  2. Macwilliams, D.S., Functional Monomers. Their Preparation, Polymerization, and Application, New York: M. Decker, 1973.

    Google Scholar 

  3. Fournand, D., Fournand, D., Vaysse, L., Dubreucq, E., Arnaud, A., and Galzy, P., J. Mol. Cat. B: Enzymatic, 1998, vol. 5, nos. 1–4, pp. 207–211.

    Article  CAS  Google Scholar 

  4. Kobayashi, M., Goda, M., and Shimizu, S., Biochem. Biophys. Res. Commun., 1999, vol. 256, no. 2, pp. 415–418.

    Article  PubMed  CAS  Google Scholar 

  5. Fournand, D. and Arnaud, A., J. Appl. Microbiol., 2001, vol. 91, no. 3, pp. 381–393.

    Article  PubMed  CAS  Google Scholar 

  6. Lavrov, K.V., Zalunin, I.A., Kotlova, E.K., and Yanenko, A.S., Biochemistry (Moscow), 2010, vol. 75, no. 8, pp. 1006–1013.

    Article  CAS  Google Scholar 

  7. Galaev, I.Yu., Usp. Khim., 1995, vol. 64, no. 5, pp. 505–524.

    Article  CAS  Google Scholar 

  8. Shvyadas, V.K., Galaev, I.Yu., Semiletov, Yu.A., and Korshunova, G.A., Bioorg. Khim., 1983, vol. 9,8, pp. 1139–1141.

    Google Scholar 

  9. Plaut, H. and Ritter, J., J. Am. Chem. Soc., 1951, vol. 73, pp. 4076–1077.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. State Research Institute for Genetics and Selection of Industrial Microorganisms, Moscow, 117545, Russia

    K. V. Lavrov, G. A. Larikova & A. S. Yanenko

Authors
  1. K. V. Lavrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. A. Larikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. S. Yanenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. S. Yanenko.

Additional information

Original Russian Text © K.V. Lavrov, G.A. Larikova, A.S. Yanenko, 2012, published in Biotekhnologiya, 2012, No. 4, pp. 26–30.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lavrov, K.V., Larikova, G.A. & Yanenko, A.S. Novel biocatalytic process of N-substituted acrylamide synthesis. Appl Biochem Microbiol 49, 702–705 (2013). https://doi.org/10.1134/S0003683813080048

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0003683813080048

Keywords

Search

Navigation