Influence of side-chain-terminating moieties on the conformation of branched polypeptides and their conjugates with 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone

Biophys Chem. 1988 Aug;31(1-2):53-61. doi: 10.1016/0301-4622(88)80008-5.

Abstract

Poly(Lys-(Xi-DL-Alam] polypeptides carrying hydrophilic (X = His, Glu, Lys) or hydrophobic (X = Nle, Ile, Phe) amino acid residues and their conjugates with 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone were synthesized. The conformational properties of carrier polypeptides and conjugates were studied by circular dichroism (CD) spectroscopy in the wavelength regions 190-250 and 310-380 nm, with the emphasis on analysis under near physiological conditions. Based on CD studies, it could be demonstrated that the helix-forming capacity appears to be related to the hydrophobic nature of the branch-terminating amino acid of the branched polypeptides. With respect to carrier function, the presence of a coupled derivative of oxazolone at the side chain termini generally promotes the formation of helical secondary structure. The absolute configuration of the side-chain-terminating amino acids was found to be important for the local orientation of the hapten molecule in the conjugates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Circular Dichroism
  • Haptens*
  • Models, Molecular
  • Oxazoles*
  • Oxazolone*
  • Peptides*
  • Protein Conformation*
  • Structure-Activity Relationship

Substances

  • Haptens
  • Oxazoles
  • Peptides
  • Oxazolone