Description

• General description: (N-Isocyanoimino)triphenylphosphorane (Pinc) is a bench-stable solid reagent widely used in organic synthesis. It is an amphoteric compound with unique properties that make it a versatile tool for various applications, including heterocycle synthesis and macrocyclization of peptides. Pinc facilitates cyclization and incorporation of a conformational control element into peptide macrocycles, leading to desired drug properties such as improved membrane permeability, lipophilicity, and aqueous solubility.[1] Its ability to form oxadiazoles offers opportunities for the development of new transformations.
• Application: As reported by the lab of Andrei Yudin, Pinc enables zwitterionic-controlled generation of peptide macrocyles from linear peptides and aldehydes. It enables the formation of disubstituted 1,3,4-oxadiazoles by intercepting the key mixed anhydride characteristic of the Ugi reaction.[2] Furthermore, the resulting peptide macrocycles containing oxadiazole exhibit improved drug properties such as cell-permeability and a rigid conformation.[3]
• Features and Benefits: Bench-stable solid: Pinc is a stable reagent that can be easily handled and stored.Facilitates cyclization and incorporation of conformational control element: Pinc enables the formation of peptide macrocycles with a desired conformation, leading to improved drug properties.Amphoteric properties: Pinc′s amphoteric nature allows for the design of new multicomponent reactions, expanding its synthetic capabilities.Desired drug properties: The resulting peptide macrocycles exhibit enhanced membrane permeability, lipophilicity, and aqueous solubility, making them desirable for drug development.Versatile transformations: Pinc′s ability to form oxadiazoles opens up opportunities for the development of novel synthetic transformations.