Synonyms: Pinc
Molecular Formula: C19H16N2P
Molecular Weight: 303.32
Linear Structural Formula: C19H16N2P
MDL Number: MFCD09038528
Purity: 95%
Application: 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).
Other Notes: Oxadiazole grafts in peptide macrocyclesC&EN Highlight: Cyclic peptides with heterocycles are cell membrane-permeableTechnology Spotlight: Heterocycle and Cyclic Peptide Formation with Pinc