Litcius/Paper detail

Katritzky Salts for the Synthesis of Unnatural Amino Acids and Late‐Stage Functionalization of Peptides

Ali Munaim Yousif, Stefania Colarusso, Elisabetta Bianchi

2022European Journal of Organic Chemistry40 citationsDOI

Abstract

Abstract Peptide drug discovery often benefits from the large structural diversity permitted by unnatural amino acids (UAAs). Indeed, numerous approved peptide drugs include UAAs in their sequences. Therefore, innovative chemical approaches either to synthesize UAAs or to allow late‐stage functionalization of peptides are emerging themes in peptide drug discovery. Thanks to the recent advances in deaminative strategies using alkylpyridiniums salts, often referred to as Katritzky salts, a variety of radical alkylation methods have been developed. In recent years the use of Katritzky salts have become popular in peptide chemistry due to their ease of preparation from a primary amine, which is a predominant functional group in amino acids. This review highlights the progress that has been made by using Katritzky salts in the synthesis of UAAs, late‐stage peptide functionalization, and peptide macrocyclization.

Topics & Concepts

ChemistryPeptideAmino acidCombinatorial chemistrySurface modificationPosttranslational modificationOrganic chemistryBiochemistryEnzymePhysical chemistryChemical Synthesis and AnalysisRadical Photochemical ReactionsCatalytic C–H Functionalization Methods