2 - Synthesis of Pseudopeptides

Abstract

This chapter describes the synthesis of pseudopeptides. Pseudopeptides or amide bond surrogates are the terms that can be used to describe backbone-modified peptides. These synthetic analogs of peptides have a variety of potential uses, but the most of the interest in these areas focuses on their potential for developing metabolically stabilized and orally active peptide hormone analogs or enzyme inhibitors with enhanced biological potency. In considering a generalized peptide backbone, the modifications to the side chains A (these are usually amino acid substitutions), to the α carbon B (among the possibilities are α-aza, α-alkyl, or α, β-dehydroamino acids), or to the components of the amide or peptide bond itself C , either singularly or in combination. Visualization of the amide bond replacements can be understood if the three-letter or one-letter amino acid designation codes are retained, while specifying the changes that occur among the α carbons.