Peptoids

Peptoids

Poly-N-alkylated glycines (or peptoids) are a family of peptidomimetics whose side chains are appended to the nitrogen atom of the peptide backbone (in comparison to peptides whose side-chain is located on the α-carbon) (Figure 1.).

Peptoids figure 1
Figure 1.

 

These compounds are not found in nature but they have been shown to mimic and, in some cases, exceed the biological activity of natural peptides. Additionally, peptoids are resistant to proteolytic degradation and are able to adopt a stable helical structure.

The synthesis of peptoids can be performed quickly and relatively inexpensively on solid-phase, making peptoids attractive targets for both high and low-throughput screening. Figure 2. (below) illustrates the solid-phase assembly of a generic peptoid using a sub-monomer approach1 which can be fully automated. Synthesis proceeds via repetition of activation (acylation)/amination steps.

The structural diversity of peptoids is potentially vast due to the commercial availability of a wide range of substituted amines.

Peptoids figure 2
Figure 2.

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1. Zuckermann et. al. J. Med. Chem. 1994, 37, 2678-2685.