Site-selective editing of peptides <i>via</i> backbone modification

Shi, Junjie; Sun, Tong; Yang, Mingyu

doi:10.1039/d3qo01980b

Org. Chem. Front.

2024

DOI: 10.1039/d3qo01980b

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Site-selective editing of peptides via backbone modification

Junjie Shi,

Tong Sun,

Mingyu Yang

Abstract: The site-selective editing of peptides and proteins through backbone modification holds significant promise in the realms of therapeutic and diagnostic agents, drug development, and biological tool compounds. Even subtle alterations...

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Recent Progress on Transition Metal Catalyzed Macrocyclizations Based on C−H Bond Activation at Heterocyclic Scaffolds

Das,

Pradhan,

Samanta

2024

Chemistry An Asian Journal

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Macrocycles are essential in protein‐protein interactions and the preferential intake of bioactive scaffolds. Macrocycles are commonly synthesized by late‐stage macrolactonizations, macrolactamizations, transition metal‐catalyzed ring‐closing metathesis, S‐S bond‐forming reactions, and copper‐catalyzed alkyne–azide cycloaddition. Recently, transition metal‐catalyzed C‐H activation strategies have gained significant interest among chemists to synthesize macrocycles. This article provides a comprehensive overview of the transition metal‐catalyzed macrocyclization via C‐H bond functionalization of heterocycle‐containing peptides, annulations, and heterocycle‐ring construction through direct C‐H bond functionalization. In the first part, palladium salt catalyzed coupling with indolyl C(sp3)‐H and C(sp2)‐H bonds for macrocyclization is reported. The second part summarizes rhodium‐catalyzed macrocyclizations via site‐selective C‐H bond functionalization. Earth‐abundant, less toxic 3d metal salt Mn‐catalyzed cyclizations are reported in the latter part. This summary is expected to spark interest in emerging methods of macrocycle production among organic synthesis and chemical biology practitioners, helping to develop the discipline. We hope that this mini‐review will also inspire synthetic chemists to explore new and broadly applicable C‐C bond‐forming strategies for macrocyclization via intramolecular C‐H activation.

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Recent Progress on Transition Metal Catalyzed Macrocyclizations Based on C−H Bond Activation at Heterocyclic Scaffolds

Das,

Pradhan,

Samanta

2024

Chemistry An Asian Journal

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Molecular Editing of Toluene by Sequential meta-C–H/Benzylic C–N Deaminative Functionalizations

Jiang,

He,

Yan

et al. 2024

Org. Lett.

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An approach to synthesizing structurally diverse toluene derivatives via sequential meta-C−H and benzylic C−N deaminative functionalization was developed by using a recyclable bifunctional directing template. The functionalized Katritzky salt intermediates are shown to be engaged in a wide range of carbon−carbon and carbon−heteroatom bond formation reactions. The synthetic utility of the strategy was demonstrated by late-stage functionalization of toloxatone.

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Site-selective editing of peptides via backbone modification

Abstract: The site-selective editing of peptides and proteins through backbone modification holds significant promise in the realms of therapeutic and diagnostic agents, drug development, and biological tool compounds. Even subtle alterations...

Cited by 2 publications

References 63 publications

Recent Progress on Transition Metal Catalyzed Macrocyclizations Based on C−H Bond Activation at Heterocyclic Scaffolds

Recent Progress on Transition Metal Catalyzed Macrocyclizations Based on C−H Bond Activation at Heterocyclic Scaffolds

Molecular Editing of Toluene by Sequential meta-C–H/Benzylic C–N Deaminative Functionalizations

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