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Synthesis 2019; 51(09): 1913-1922
DOI: 10.1055/s-0037-1612418
DOI: 10.1055/s-0037-1612418
short review
Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions
We thank the Council of Scientific and Industrial Research (CSIR), New Delhi [02(0272)/16/EMRII] and the Department of Science and Technology (DST), New Delhi (EMR/2015/002053, SR/S2/JCB-33/2010) for financial support. S.K. thanks the Department of Science and Technology (DST) for the award of a J. C. Bose fellowship (SR/S2/JCB-33/2010) and Praj Industries, Pune for the Pramod Chaudhari Chair Professorship (Green Chemistry).Further Information
Publication History
Received: 11 December 2018
Accepted after revision: 13 February 2019
Publication Date:
25 March 2019 (online)
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
-
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