Synthesis of a proposed antigenic hexapeptide from Escherichia coli K88 protein fimbriae

Acta Chem Scand B. 1986 Apr;40(4):235-41. doi: 10.3891/acta.chem.scand.40b-0235.

Abstract

The hexapeptide Boc-Asp-Asp-Tyr-Arg-Gln-Lys-OMe is assembled by stepwise synthesis in solution with an overall yield of 44%. N alpha-boc-amino acids, protected with benzyl or benzyloxycarbonyl groups in the side-chains, are coupled as active estes of 1-hydroxybenzotriazole in mixtures of dichloromethane and N,N-dimethylformamide. N alpha-deprotection is accomplished with trifluoroacetic acid. Finally, hydrogenation with palladium on charcoal and ammonium formate produces the pure hexapeptide. A new one-pot synthesis of Boc-Arg(Z2) is described, and the use of this derivative in peptide coupling is studied. The synthetic peptide was coupled to BSA and used in direct immunication of rabbits.

MeSH terms

  • Antigens, Bacterial*
  • Escherichia coli / immunology*
  • Fimbriae, Bacterial / immunology*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Oligopeptides / chemical synthesis*
  • Optical Rotation

Substances

  • Antigens, Bacterial
  • Indicators and Reagents
  • Oligopeptides