Skip to main content
SpringerLink
Log in

Enzymatic Synthesis of γ-Glutamylmethylamide from Glutamic Acid γ-Methyl Ester and Methylamine Catalyzed by Escherichia coli Having γ-Glutamyltranspeptidase Activity

  • Published:
Applied Biochemistry and Biotechnology Aims and scope Submit manuscript

Abstract

A new method for the synthesis of γ-glutamylmethylamide is presented. Glutamic acid γ-methyl ester was used as substrate for γ-glutamylmethylamide synthesis catalyzed by Escherichia coli with γ-glutamyltranspeptidase activity. Reaction conditions were optimized by using 300 mM glutamic acid γ-methyl ester and 3,000 mM methylamine at pH 10 and 40 °C. Bioconversion rate of γ-glutamylmethylamide reached 87 % after 10 h. γ-Glutamyltranspeptidase was reversibly inhibited only when glutamic acid γ-methyl ester was above 300 mM.

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

Scheme 1
Fig. 1
Fig. 2
Scheme 2

References

  1. Yokogoshi, H., & Kobayashi, M. (1998). Life Sci, 62, 1065–1068.

    Article  CAS  Google Scholar 

  2. Yokogoshi, H. (1998). Japan patent 2000053567A.

  3. Chen, Y., Scanlan, J., Song, L. J., Crombie, A., Rahman, M. T., Schäfer, H., & Murrell, J. C. (2010). Appl Environ Microbiol, 76, 4530–4537. doi:10.1128/AEM.00739-10.

    Article  CAS  Google Scholar 

  4. Lichtenstein, N. (1942). J Am Chem Soc, 64, 1021–1022.

    Article  CAS  Google Scholar 

  5. Kung, H. F., & Wagner, C. (1969). J Biol Chem, 244, 4136–4140.

    CAS  Google Scholar 

  6. Barnes, E. M., Jr., Zimniak, P., & Jayakumar, A. (1983). J Bacteriol, 156, 752–757.

    CAS  Google Scholar 

  7. Kimura, T., Sugahara, I., Hayashi, K., Kobayashi, M., & Ozeki, M. (1990). Agric Biol Chem, 54, 2819–2826.

    Article  CAS  Google Scholar 

  8. Tachiki, T., Yamada, T., Mizuno, K., Ueda, M., Shiode, J., & Fukami, H. (1998). Biosci Biotechnol Biochem, 62, 1279–1283.

    Article  CAS  Google Scholar 

  9. Tate, S. S., & Meister, A. (1981). Mol Cell Biochem, 39, 357–368.

    Article  CAS  Google Scholar 

  10. Suzuki, H., Yamada, C., & Kato, K. (2007). Amino Acids, 32, 333–340.

    Article  CAS  Google Scholar 

  11. Hou, X., Yu, Q., Zeng, F., Yu, C., & Wu, S. (2014). Chem Commun (Camb). 4, 50(26), 3417–3420. doi:10.1039/c4cc00473f.

    Article  CAS  Google Scholar 

  12. Ida, T., Suzuki, H., Fukuyama, K., Hiratake, J., & Wada, K. (2014). Acta Crystallogr D Biol Crystallogr, 70(Pt 2), 607–614. doi:10.1107/S1399004713031222.

    Article  CAS  Google Scholar 

  13. Zheng, R. C., Zheng, Y. G., & Shen, Y. C. (2007). Biotechnol Lett, 29, 1087–1091.

    Article  CAS  Google Scholar 

  14. Zhang, F., Zheng, Q. Z., Jiao, Q. C., Liu, J. Z., & Zhao, G. H. (2010). Biotechnol Lett, 32, 1147–1150. doi:10.1007/s10529-010-0273-1.

    Article  CAS  Google Scholar 

  15. Suzuki, H., Kumagai, H., & Tochikura, T. (1986). J Bacteriol, 168, 1325–1331.

    CAS  Google Scholar 

  16. Zhang, H. J., Zhan, Y. P., Chang, J. J., Liu, J. Z., Xu, L. S., Wang, Z. Y., Liu, Q., & Jiao, Q. C. (2012). Biotechnol Lett, 34, 1931–1935. doi:10.1007/s10529-012-1000-x.

    Article  Google Scholar 

  17. Suzuki, H., Izuka, S., Miyakawa, N., & Kumagai, H. (2002). Enzyme Microb Tech, 31, 884–889.

    Article  CAS  Google Scholar 

  18. Okada, T., Suzuki, H., Wada, K., Kumagai, H., & Fukuyama, K. (2006). Proc Natl Acad Sci U S A, 103, 6471–6476.

    Article  CAS  Google Scholar 

  19. Inoue, M., Hiratake, J., Suzuki, H., Kumagai, H., & Sakata, K. (2000). Biochemistry, 39, 7764–7771.

    Article  CAS  Google Scholar 

  20. Bridge, W.J., Zarka, M.H. (2006). WO patent 2006/102722 A1.

Download references

Acknowledgments

This study was supported by the Anhui Province College Excellent Young Talents Fund Project of China “Molecular modification of tryptophan synthetase and chiral catalysis research” (2013SQRL086ZD) and Key project of natural science in Anhui province department of education (KJ2012A264).

Author information

Authors and Affiliations

  1. Department of Chemistry and Life Science, Suzhou University, Suzhou, 234000, People’s Republic of China

    Lisheng Xu, Guizhen Gao, Cao Wengen, Jigui Xu, Liang Zhao, Hongwei Shi & Xingtao Zhang

Authors
  1. Lisheng Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Guizhen Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Cao Wengen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jigui Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Liang Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hongwei Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Xingtao Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Lisheng Xu.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xu, L., Gao, G., Wengen, C. et al. Enzymatic Synthesis of γ-Glutamylmethylamide from Glutamic Acid γ-Methyl Ester and Methylamine Catalyzed by Escherichia coli Having γ-Glutamyltranspeptidase Activity. Appl Biochem Biotechnol 173, 851–856 (2014). https://doi.org/10.1007/s12010-014-0877-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12010-014-0877-3

Keywords

Search

Navigation