Skip to main content
SpringerLink
Log in

Chemical transformations of the condensation products of pyridoxal with L-α-alanine and D-α-alanine

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

The kinetics and mechanism of the reactions of pyridoxal with L- and D-α-alanine were studied. Under comparable conditions, the condensation of L- and D-α-alanines with pyridoxal includes three kinetically different steps. The first fast step is addition of the amino acid to pyridoxal with formation of the corresponding amino alcohol, the second (slower) step is dehydration of the amino alcohol to give Schiff base, and the third (very slow) step is elimination of α-hydrogen atom from the L-α-amino acid fragment or decarboxylation of the D-α-amino acid fragment, followed by isomerization of the Schiff base to quinoid structure whose subsequent hydrolysis yields pyridoxamine and pyruvic acid or acetaldehyde, respectively. A scheme was proposed for chemical transformations of the pyridoxal condensation products with L- and D-α-alanines.

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

References

  1. Metzler, D.E., Biochemistry: The Chemical Reactions of Living Cells, New York: Academic, 1977. Translated under the title Biokhimiya, Moscow: Mir, 1980, vol. 2, p. 209.

    Google Scholar 

  2. Braushtein, A.E. and Shemyakin, M.M., Biokhimiya, 1953, vol. 18, no. 4, p. 393.

    Google Scholar 

  3. Pishchugin, F.V. and Tuleberdiev, I.T., Russ. J. Gen. Chem., 2005, vol. 75, no. 9, p. 1465.

    Article  CAS  Google Scholar 

  4. Pishchugin, F.V. and Shershenalieva, Z.Sh., Biokhimiya, 1988, vol. 53, no. 9, p. 1509.

    CAS  Google Scholar 

  5. Dunathan, H.C., Adv. Enzymol. Relat. Areas Mol. Biol., 1971, vol. 35, p. 79.

    Article  CAS  Google Scholar 

  6. Bailey, G.E., Chotamangsa, O., and Vuttirej, K., Biochemistry, 1970, vol. 9, no. 16, p. 3243.

    Article  CAS  Google Scholar 

  7. Shye, G.E., Potts, R., and Floss, H.G., J. Am. Chem. Soc., 1974, vol. 96, no. 5, p. 1593.

    Article  Google Scholar 

  8. Metzler, D.E. and Harris, J.A., Biochemistry, 1973, vol. 12, no. 26, p. 5377.

    Article  CAS  Google Scholar 

  9. Laidler, K.J., Reaction Kinetics, Oxford: Pergamon, 1963. Translated under the title Kinetika organicheskikh reaktsii, Moscow: Mir, 1966, p. 31.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry and Chemical Technology, National Academy of Sciences of Kirgizia, pr. Chui 267, Bishkek, 720071, Kirgiziya

    F. V. Pishchugin & I. T. Tuleberdiev

Authors
  1. F. V. Pishchugin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. T. Tuleberdiev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to F. V. Pishchugin.

Additional information

Original Russian Text © F.V. Pishchugin, I.T. Tuleberdiev, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 1, pp. 120–123.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pishchugin, F.V., Tuleberdiev, I.T. Chemical transformations of the condensation products of pyridoxal with L-α-alanine and D-α-alanine. Russ J Gen Chem 79, 117–120 (2009). https://doi.org/10.1134/S1070363209010174

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363209010174

Keywords

Search

Navigation