Protocol

Protein Design

Volume 340 of the series Methods in Molecular Biology pp 95-109

Design and Synthesis of β-Peptides With Biological Activity

  • Marc J. KoyackAffiliated withDepartment of Chemistry, University at Buffalo, The State University of New York
  • , Richard P. ChengAffiliated withDepartment of Chemistry, University at Buffalo, The State University of New York

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Abstract

β-Peptides have been used as a platform for developing bioactive compounds with various types of bioactivity such as antimicrobial activity, cholesterol absorption inhibition, somatostatin receptor agonist, and hDM2 inhibition. These bioactive β-peptides have been designed based on bioactive a-peptides. Three main strategies have been used to design bioactive β-peptides: direct conversion of a-peptide sequences into β-peptide sequences, placement of side chains to provide desirable distribution of physicochemical properties, and the grafting of proteinaceous side chains critical for bioactivity onto β-peptide structures. This chapter briefly discusses the various strategies employed to design bioactive β-peptides, followed by protocols for the synthesis of N-α-fluorenylmethyloxycarbonyl (Fmoc)-protected β3-amino acids from Fmoc-protected α-amino acids, and synthesis of β-peptides by solid phase methods using Fmoc-based chemistry.

Key Words

β-Amino acids bioactivity foldamers β-peptides rational design