Despite growing interest for therapeutic and other biological applications, cyclic peptidomimetics are challenging to synthesize. As reported by the lab of
Andrei Yudin, (
N-isocyanoimino)triphenylphosphorane (
Pinc) enables zwitterionic-controlled generation of peptide macrocyles from linear peptides and aldehydes. Containing a 1,3,4-oxadiazole, the resulting peptide exhibits both improved membrane permeability, lipophilicity, and aqueous solubility.
Different functional groups can be introduced by varying the aldehyde, and initial work used propionaldehyde (
538124), phenylacetaldehyde (
107395), and isovaleraldehyde (
146455).
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