Palladium-Catalyzed Late-Stage Functionalization of Phenylalanine and Phenylalanine Derived Peptides DOI
Hisashi Yamamoto,

Isai Ramakrishna

Synfacts, Journal Year: 2023, Volume and Issue: 19(10), P. 1056 - 1056

Published: Sept. 14, 2023

Key words late-stage peptide functionalization - palladium catalysis tandem reaction benzoquinone

Language: Английский

Backbone-enabled modification of peptides with benzoquinone via palladium-catalyzed δ-C(sp2)–H functionalization DOI

Fengjie Lu,

Yi Sun, Yaning Liu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(13), P. 1754 - 1757

Published: Jan. 1, 2024

Backbone-enabled site-selective modification of peptides with benzoquinone via Pd-catalyzed δ-C(sp 2 )–H functionalization has been achieved.

Language: Английский

Citations

7
Endogenous group‐directed late‐stage C‐H functionalization of peptides DOI
Aman Singh Barahdia,

Karuna Thakare,

Lipat Kaur

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 2844 - 2858

Published: May 18, 2024

Abstract Peptides are diverse in terms of their functional groups and side‐chain functionalities, late‐stage C−H functionalization plays a crucial role design. Approaches for such synthesis require pre‐installation post‐removal the directing group (DG). In recent times, chemical methods have been developed, focusing on external DG‐free peptides. These approaches utilize inherent native functionality peptides as DG to simplify synthetic routes, reducing steps, waste generation, enhancing sustainability, cost‐effectiveness, operational flexibility. Such facilitate both natural unnatural amino acid‐containing

Language: Английский

Citations

4
Post-synthetic Chemical Functionalization of Peptides DOI

Stephanie A. Barros,

Rosaura Padilla‐Salinas, Irini Abdiaj

et al.

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0
Backbone-Enabled and Ester Groups Switched δ-C(sp2)–H Amination/Fluorination: Cyclic Dipeptides Synthesis DOI
Jian Tang,

Fengjie Lu,

Xinyi Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(24), P. 5130 - 5135

Published: June 6, 2024

An efficient and concise strategy for the synthesis of cyclic dipeptides via Pd-catalyzed site-selective δ-C(sp2)–H amination/fluorination N-to-C cyclization is disclosed. The backbone amides within serves as endogenous directing groups, while desired products were switched by C-terminal ester group. This chemistry presents a novel robust alternative to construct cyclodipeptide fragments.

Language: Английский

Citations

3
Methionine-Enabled Peptides Modification through Late-stage Pd-catalyzed β-C(sp3)-H olefination/cyclization DOI

Fengjie Lu,

Xinyi Zhang,

Yujie Geng

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(61), P. 7942 - 7945

Published: Jan. 1, 2024

We present a method for site-selective diversification of peptides via Pd-catalyzed β-C(sp 3 )–H olefination/cyclization.

Language: Английский

Citations

3
Late-Stage Diversification of Peptides via Pd-Catalyzed Site-Selective δ-C(sp2)-H Fluorination and Amination DOI
Jian Tang,

Fengjie Lu,

Yi Sun

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(19), P. 14165 - 14171

Published: Sept. 26, 2023

Site-selective C-H fluorination is an attractive strategy for directly transforming inert bonds into C-F bonds, yet it remains a significant challenge. Herein, we have developed efficient and versatile site-selective amination of phenylalanine-containing peptides via late-stage Pd-catalyzed δ-C(sp2)-H activation, providing valuable tool the in situ synthesis fluorinated indoline scaffolds within peptides.

Language: Английский

Citations

8
Pd-Catalyzed Picolinamide-Directed C(sp2)–H Sulfonylation of Amino Acids/Peptides with Sodium Sulfinates DOI

Raghunath Bag,

Nagendra K. Sharma

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10127 - 10147

Published: June 26, 2024

This report describes a Pd-catalyzed picolinamide-directed site-selective C(sp

Language: Английский

Citations

2
Pd-Catalyzed Picolinamide-Directed Late-Stage Chalcogenation of Tryptophan-Containing Peptides DOI

Raghunath Bag,

Nagendra K. Sharma

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 15666 - 15686

Published: Oct. 26, 2023

This report describes the Pd-catalyzed late-stage chalcogenation of tryptophan-containing peptides with disulfides/diselenides in moderate to good yields. It comprises broad substrate scope, functional group diversity, modification drug molecules, and various valuable synthetic transformations, including room temperature easy removal picolinamide auxiliary, which could be applicable tune structure function peptides.

Language: Английский

Citations

6
Pd-Catalyzed Picolinamide-Directed C(sp2)-H Sulfonylation of Amino Acids/Peptides with Sodium Sulfinates DOI Creative Commons
Nagendra K. Sharma,

Raghunath Bag

Published: March 5, 2024

This report describes a Pd-catalyzed picolinamide-directed site-selective C(sp2)-H sulfonylation of amino acids and peptides with sodium sulfinate in moderate to good yields. Sulfonylation levodopa dopamine drug molecules late-stage di-rected peptide are studied for the first time. Broad substrate scope having various functionalities, modifications, post synthetic utilities such as chalcogenation, bromination, olefination, arylation potential ad-vantages.

Language: Английский

Citations

0
Palladium-Catalyzed Late-Stage Functionalization of Phenylalanine and Phenylalanine Derived Peptides DOI
Hisashi Yamamoto,

Isai Ramakrishna

Synfacts, Journal Year: 2023, Volume and Issue: 19(10), P. 1056 - 1056

Published: Sept. 14, 2023

Key words late-stage peptide functionalization - palladium catalysis tandem reaction benzoquinone

Language: Английский

Citations

0