Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 52, Pages 6346-6359Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc01795k
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Funding
- Advanced Catalytic Transformation Program for Carbon Utilization (ACT-C) from the Japan Society and Technology Agency (JST) [JPMJCR12ZD]
- Japan Society for the Promotion of Science (JSPS) [JP17H06142]
- DAIKO FOUNDATION
- Takeda Science Foundation
- Adaptable and Seamless Technology Transfer Program through Target-driven RD (A-STEP)
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The article discusses the development of methods for amide bond formation without typical condensation reagents, presenting a metal-templated macrolactamisation approach that addresses long-standing challenges in peptide chemistry through substrate control.
The development of methods for amide bond formation without recourse to typical condensation reagents has become an emerging research area and has been actively explored in the past quarter century. Inspired by the structure of vitamin B-12, we have developed a metal-templated macrolactamisation that generates a new wave towards classical macrolactam synthesis. Further, distinct from the extensively used methods with condensation reagents or catalysts based on catalyst/reagent control our metal-catalysed methods based on substrate control can effectively address long-standing challenges such as racemisation in the field of peptide chemistry. In addition, the substrate-controlled strategy demonstrates the feasibility of remote peptide bond-forming reaction catalysed by a metal-ligand complex. Moreover, an originally designed hydrosilane/aminosilane system can avoid not only racemisation but also unnecessary waste production. This feature article documents our discovery and application of our original approaches in amide bond formation.
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