Transformation of a Biologically Active Peptide into Peptoid Analogs While Retaining Biological Activity

Title: Transformation of a Biologically Active Peptide into Peptoid Analogs While Retaining Biological Activity

Volume: 13 Issue: 8

Author(s): Berit Hoffmann, Thomas Ast, Thomas Polakowski, Ulrich Reineke and Rudolf Volkmer

Affiliation:

Keywords: SPOT synthesis, peptidomimetic, peptoid, peptomer, peptid-peptoid transformation

Abstract: We report the stepwise transformation of a linear peptide epitope recognized by the anti-transforming growth factor a monoclonal antibody Tab2 into peptomers and finally into peptoid analogs. The key experiment in this study is the substitution analysis in which each position of the peptide is exchanged by a set of different peptoid building blocks resulting in a peptidomimetic array. After probing the array toward antibody binding, the best binding peptomer spots were selected and subjected to a successive transformation. The best peptoid found in this study has a KD of 200 nM when binding to Tab2, which is only 8-fold higher than the starting peptide. Moreover, this approach permits to ask directly questions about the transformation of peptide lead structures into non-peptidic compounds in the context of protein recognition.

Cite this article as:

Hoffmann Berit, Ast Thomas, Polakowski Thomas, Reineke Ulrich and Volkmer Rudolf, Transformation of a Biologically Active Peptide into Peptoid Analogs While Retaining Biological Activity, Protein & Peptide Letters 2006; 13 (8) . https://dx.doi.org/10.2174/092986606777841299