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[9] Wilding JPH, et al

Notably 16 , devoid of a macrocyclic ring system in the N-terminal is not selective and inhibits both IRAP and AP-N activity, suggesting that introduction of proper conformational constrains in the N-terminal by macrocyclization improves selectivity (Axn et al., 2007)

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This approach inspired other programmes: N-hexanoic-Tyr-D-Arg : enkephalin-derived, protease-resistant, studied for pain N-methyl-Aib inclusions : N-methyl substitutions increase membrane permeability at the cost of partial loss of receptor affinity Beta-peptides and D-amino acids : substitution of natural chiral residues by their D enantiomers, making the peptide invisible to endogenous proteases while (sometimes) preserving function Stapled peptides : hydrocarbon cyclisation, popularised by Verdine (Harvard), stabilises alpha helices and improves cellular penetration These strategies progressively shift the peptide / small molecule frontier

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10.1159/000320288 66 MoklasM.Nurul RaudzahA.Taufik HidayatM.SharidaF.Farah IdayuN.ZulkhairiA.et al (2008)