...and Peptoid Polygons

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Science  16 Mar 2007:
Vol. 315, Issue 5818, pp. 1467
DOI: 10.1126/science.315.5818.1467c

The potential therapeutic usefulness of peptides is often limited by their degradation via proteolysis, and a number of peptide mimics have been developed that avoid degradation by using a different backbone linkage. Peptoids, which are composed of glycine monomers substituted at the nitrogen atom, can develop helical secondary structure if they bear bulky chiral side chains, but in solution they often exhibit some disordering and conformational heterogeneity. Shin et al. show that the use of the peptide coupling agent PyBOP led to remarkably efficient head-to-tail cyclization of peptoids with methoxyethyl, phenylmethyl, and azidopropyl side chains. Products ranging from cyclic pentamers up to cyclic 20-mers could be prepared with yields of ∼90% or greater. These compounds have sufficient conformational ordering that several could be crystallized for structural analysis by x-ray diffraction. — PDS

J. Am. Chem. Soc. 129, 10.1021/ja066960o (2007).

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