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Peptoids的微波合成

 发布时间:2012-06-29 点击量:1207

INTRODUCTION

Peptoids are polymers of various (N-alkyl) glycines.1 While they are similar in structure to peptides (Figure 1), peptoids lack a peptide bond making them resistant to proteolytic activity in vivo1,2. This stability makes peptoids an attractive peptidomimetic target for drug discovery and development.

Figure 1. Comparison of peptide and peptoid structure.

Peptoids are generally synthesized through a “sub-monomer” process consisting of two steps; an acylation step using bromoacetic acid and N,N’-diisopropylcarbodiimide (DIC) followed by reaction with a primary amine via nucleophilic displacement of the bromide (Figure 2).1

Figure 2. General synthesis of peptoids.

Because many structurally diverse monosubstituted amines are commercially available, peptoids with a wide variety of side chains can be readily synthesized.2,3 However, conventional synthesis of peptoids can take up to three hours per residue.1 Microwave irradiation has been shown to significantly.

Figure 3. 9-mer peptoid.

 
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