Skip to main content
Log in

Synthesis of diethanolamides of N-lauroyl dipeptides and correlation of their structures with surfactant and antibacterial properties

  • Published:
Journal of the American Oil Chemists Society

Abstract

Diethanolamides (DEA) of proteins possess nonionic skin-compatible, biodegradable, surfactant and antibacterial properties. The DEA of dipeptides are, however, too hydrophilic to be effective surfactants. Hence, DEA of N-lauroyl dipeptides were synthesized and their surfactant and antibacterial properties were correlated with the structures of amino acid moieties. N-Lauroyl condensates of five simple amino acids were coupled with the corresponding amino acid methyl esters and the resulting products were condensed with diethanolamine in the presence of sodium methoxide to yield DEA of N-lauroyl dipeptides. The DEA of N-lauroyl glycine dipeptide showed surfactant properties comparable to lauroyl diethanolamide. The thiol group in the cysteine derivative exerted an unfavorable effect on surfactant properties. The isobutyl side chain in the leucine derivative contributed greatly to the antibacterial activity when compared to the other amino acid derivatives studied.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Griffin, W.C.,J. Soc. Cosmet. Chemists. 5:249 (1954).

    Google Scholar 

  2. Schick, M.,Nonionic Surfactants, Marcel Dekker, New York, NY, 1967, pp. 1–7.

    Google Scholar 

  3. Young, H.H., W. Springs and K.H. Spitzmueller, U.S. Patent 3,230,210 (1966).

    Google Scholar 

  4. Tamer, E., O. Schneiders and Quaedulieg, Belgian Patent 642,397 (1966).

  5. Cocks, L.V., and C. van Rede,Laboratory Handbook for Oils and Fats Analysis, Academic Press, New York, NY, 1966, p. 30.

    Google Scholar 

  6. Ross, J., and G.D. Miles,Oil and Soap 18:99 (1941).

    Article  CAS  Google Scholar 

  7. Subrahmanyam, V.V.R., and K.T. Achaya,J. Chem. and Eng. Data 6 (no.1): 38 (1961).

    Article  CAS  Google Scholar 

  8. Salle, A.J.,Fundamental Principles of Bacteriology, McGraw-Hill Book Company, Inc., New York, NY, 1961.

    Google Scholar 

  9. Jungermann, E., J.F. Geretch and I.J. Krems,J. Am. Chem. Soc. 78:172 (1956).

    Article  CAS  Google Scholar 

  10. Heitmann, P.,Eur. J. Biochem. 3:346 (1968).

    Article  CAS  Google Scholar 

  11. Bodanszky, M.,Acta Chim. Acad. Sci. Hung. 10:335 (1957).

    CAS  Google Scholar 

  12. Vaughan, J.R., and R.L. Osato,J. Am. Chem. Soc. 74:676 (1952).

    Article  CAS  Google Scholar 

  13. Winitz, M., L. Bloch-Frankenthel, N. Izumiya, S.M. Birnhaum, C.K. Baber and J.P. Greenstein, Ibid.:2423 (1956).

    Article  CAS  Google Scholar 

  14. Gast, L.E., W.J. Schneider and J.C. Cowan,J. Am. Oil Chem. Soc. 43:418 (1966).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

IICT Communication No. 2830.

About this article

Cite this article

Mhaskar, S.Y., Lakshminarayana, G. Synthesis of diethanolamides of N-lauroyl dipeptides and correlation of their structures with surfactant and antibacterial properties. J Am Oil Chem Soc 69, 643–646 (1992). https://doi.org/10.1007/BF02635803

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02635803

Key words

Navigation