Premium
Decarboxylative couplings as versatile tools for late‐stage peptide modifications
Author(s) -
Malins Lara R.
Publication year - 2018
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.533
H-Index - 7
ISSN - 2475-8817
DOI - 10.1002/pep2.24049
Subject(s) - decarboxylation , nucleophile , combinatorial chemistry , peptide , chemistry , amino acid , peptide bond , surface modification , organic chemistry , biochemistry , catalysis
While strategies for the late‐stage modification of peptides are crucial to the design and synthesis of new peptide‐based materials and therapeutics, synthetic methods have historically focused on the modification of select, nucleophilic amino acids. This review highlights decarboxylative coupling strategies as emerging tools for the targeted functionalization of native peptidic acids—α‐carboxylic acids and aspartic/glutamic acid residues—through complexity building CC and Cheteroatom bond formations. Decarboxylation strategies employing both activated carboxylic acids (redox‐active esters) and the direct application of unprotected carboxylic acids are discussed. Emphasis is placed on the scope and limitations of the methodologies as well as their compatibility with complex peptide substrates.