Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions

Abstract

We have summarized diverse synthetic approaches for the modification of peptides by employing transition-metal-catalyzed reactions. These methods can deliver unusual peptides suitable for peptidomimetics. To this end, several popular reactions such as Diels–Alder, 1,3-dipolar cycloaddition, [2+2+2] cyclotrimerization, metathesis, Suzuki­–Miyaura cross-coupling, and Negishi coupling have been used to assemble modified peptides by post-assembly chemical modification strategies. 1 Introduction 2 Synthesis of a Cyclic α-Amino Acid Derivative via a Ring-Closing Metathesis Protocol 3 Peptide Modification Using a Ring-Closing Metathesis Strategy 4 Peptide Modification via a [2+2+2] Cyclotrimerization Reaction 5 Peptide Modification by Using [2+2+2] Cyclotrimerization and Suzuki Coupling 6 Peptide Modification via a Suzuki–Miyaura Cross-Coupling 7 Peptide Modification via Cross-Enyne Metathesis and a Diels–Alder­ Reaction as Key Steps 8 Peptide Modification via 1,3-Dipolar Cycloaddition Reactions 9 Modified Peptides via Negishi Coupling 10 A Modified Dipeptide via Ethyl Isocyanoacetate 11 Conclusions