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

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

Journal Name: Protein & Peptide Letters

Volume 13 , Issue 8 , 2006

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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.

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

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Article Details

Year: 2006
Page: [829 - 833]
Pages: 5
DOI: 10.2174/092986606777841299
Price: $58

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