Peptides should be attractive chemical tools for drug development and chemical biology. However, they possess several undesirable drawbacks such as a proteolytic degradation, a poor bioavailability and a limited cell permeability. Thus, various peptidomimetics have been developed to overcome these defects. Among them, peptoids (N-alkylated oligoglycines) have many advantages over peptides in terms of physico-chemical and pharmacological properties. Especially, cyclic peptoids may bind to their target proteins with higher affinity because of their limited conformational flexibility. In addition, they might exhibit an enhanced cell permeability and an improved resistance against enzymatic degradation. Thus, they have been developed by several different synthetic methods including macrolactamization, ring-closing metathesis (RCM), thioaryl-mediated cyclization, etc. In addition to cyclic peptoids, complex peptoid structures in three-dimensional space which may be more rigid are presumed to be unique and useful as chemical tools for various purposes but not yet developed. Therefore, we have tried to develop complex peptoid structures. In this presentation, we will introduce our efforts on the development of interesting peptoid structures by using various ligation reactions including macrolactamization, RCM and click reaction.

Solid-phase synthesis of various peptoid structures

254th National Meeting (2017)

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