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

Key words

α-amino acids - cycloadditions - Diels–Alder reaction - metathesis­ - Negishi coupling - peptide modification - Suzuki coupling

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