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

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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; peptid-peptoid transformation; peptidomimetic; peptoid; peptomer

Document Type: Research Article


Affiliations: Institut fur Medizinische Immunologie, Charite - Universitätsmedizin Berlin, Hessische Str. 3-4,10115 Berlin, Germany.

Publication date: August 1, 2006

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  • Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.

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