Synthesis and Anti-microbial Activity of Novel Phosphatidylethanolamine-N-amino Acid Derivatives

J Oleo Sci. 2015;64(7):705-12. doi: 10.5650/jos.ess15063. Epub 2015 May 21.

Abstract

The study involved synthesis of five novel amino acid derivatives of phosphatidylethanolamine isolated from egg yolk lecithin employing a three step procedure i) N-protection of L-amino acids with BOC anhydride in alkaline medium ii) condensation of - CO2H group of N-protected amino acid with free -NH2 of PE by a peptide linkage and iii) deprotection of N-protected group of amino acids to obtain phosphatidylethanolamine-N-amino acid derivatives in 60-75% yield. The five L-amino acids used were L glycine, L-valine, L-leucine, L-isoleucine and L-phenylalanine. The amino acid derivatives were screened for anti-baterial activity against B. subtilis, S. aureus, P. aeroginosa and E. coli taking Streptomycin as reference compound and anti-fungal activity against C. albicans, S. cervisiae, A. niger taking AmphotericinB as reference compound. All the amino acid derivatives exhibited extraordinary anti-bacterial activities about 3 folds or comparable to Streptomycin and moderate or no anti-fungal activity against Amphotericin-B.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis*
  • Amino Acids / pharmacology*
  • Bacteria / drug effects*
  • Drug Evaluation, Preclinical
  • Drug Resistance, Microbial
  • Egg Yolk / chemistry
  • Fungi / drug effects*
  • Glycine / chemistry
  • Isoleucine / chemistry
  • Lecithins / chemistry
  • Leucine / chemistry
  • Phenylalanine / chemistry
  • Phosphatidylethanolamines / chemistry*
  • Phosphatidylethanolamines / isolation & purification*
  • Valine / chemistry

Substances

  • Amino Acids
  • Lecithins
  • Phosphatidylethanolamines
  • Isoleucine
  • Phenylalanine
  • Leucine
  • Valine
  • Glycine