Ruthenium(II)‐Catalyzed Selective C(sp2)−H Acyloxylation of 2‐Aroyl‐Pyridine Derivatives with Sodium Carboxylate DOI
Wenbo Ma, Tao Zheng, Linghui Gu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(3), P. 518 - 525

Published: Dec. 29, 2023

Abstract A ruthenium‐catalyzed C( sp 2 )−H acyloxylation of 2‐aroyl pyridine derivatives with simple sodium carboxylate utilizing transformable directing groups is described. This protocol features broad functional group tolerance and chemo‐ regio‐selectivity, providing the products in 45%‐84%yield. Furthermore, synthetic utility this was demonstrated by late‐stage functionalization pharmaceutical compounds. Notably, could be further transformed into a variety useful heterocycles under mild conditions.

Language: Английский

Recent developments in the cleavage, functionalization, and conjugation of proteins and peptides at tyrosine residues DOI Creative Commons
Shengping Zhang, Luis M. De Leon Rodriguez, Freda F. Li

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(29), P. 7782 - 7817

Published: Jan. 1, 2023

Peptide and protein selective modification at tyrosine residues has become an exploding field of research as constitutes a robust alternative to lysine cysteine-targeted traditional peptide/protein protocols. This review offers comprehensive summary the latest advances in tyrosine-selective cleavage, functionalization, conjugation peptides proteins from past three years. updated overview complements extensive body work on site-selective proteins, which holds significant relevance across various disciplines, including chemical, biological, medical, material sciences.

Language: Английский

Citations

29
Research progress on chemical modifications of tyrosine residues in peptides and proteins DOI
Wei Zeng,

Jianyuan Xue,

Haoxing Geng

et al.

Biotechnology and Bioengineering, Journal Year: 2023, Volume and Issue: 121(3), P. 799 - 822

Published: Dec. 11, 2023

Abstract The chemical modifications (CMs) of protein is an important technique in biology, protein‐based therapy, and material science. In recent years, there has been rapid advances the development CMs peptides proteins, providing new approaches for peptide functionalization, as well drug discovery. this review, we highlight methods chemically modifying tyrosine (Tyr) residues different regions, offering a comprehensive exposition research content related to Tyr modification. This review summarizes provides outlook on residue modification, aiming offer readers assistance site‐selective modification macromolecules facilitate application field.

Language: Английский

Citations

10
Exploring Chemical Modifications of Aromatic Amino Acid Residues in Peptides DOI
Bishwajit Paul, Modhu Sudan Maji,

Susanta Bhunia

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(22), P. 3701 - 3724

Published: May 11, 2023

Abstract The chemical diversification of biomolecules set forth a significant area research that constitutes an important intersection between chemistry and biology. Amino acids peptides are the fundamental building blocks proteins play essential roles in all living organisms. While efforts have been geared toward modification amino acid residues, particularly functionalization reactive functional groups such as lysine NH2 cysteine SH, exploration aromatic residues tryptophan, tyrosine, phenylalanine, histidine has relatively limited. Therefore, this review highlights strategies for side-chain these four peptides, with focus on elucidating underlying mechanisms. We also illustrated use modifications biological realm. 1 Introduction 2 Tryptophan Modifications 3 Tyrosine 4 Phenylalanine 5 Histidine 6 Perspectives Future Outlook

Language: Английский

Citations

9
Site-Selective C–H Amination of Phenol-Containing Biomolecules DOI Creative Commons
Carlota Girón-Elola, Ibon Sasiain, Rosalía Sánchez‐Fernández

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4383 - 4387

Published: June 7, 2023

A C-N bond-forming cross-dehydrogenative coupling of a collection Tyr-containing peptides and estrogens with heteroarenes is described. This oxidative distinguished by its scalability, operational simplicity, air tolerance enables the appendance phenothiazines phenoxazines in phenol-like compounds. When incorporated into Tb(III) metallopeptide, Tyr-phenothiazine moiety acts as sensitizer for ion, providing new tool design luminescent probes.

Language: Английский

Citations

9
Rhodium-Catalyzed Regioselective C3Ar Functionalization of Tyrosines with Maleimides and Its Late-Stage Peptide Exemplification DOI

Narendra Dinkar Kharat,

Sushma Naharwal,

Disha Tank

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7673 - 7677

Published: Oct. 19, 2023

Pyridyloxy-directed Rh(III)-catalyzed regioselective C3Ar-H alkenylation of protected tyrosines was achieved with N-aryl and N-alkyl maleimides, furnishing a series maleimide-appended tyrosine-based unnatural amino acids in good yields. Further, the late-stage exemplification strategy successfully accomplished on tyrosine-containing dipeptides, tripeptides, tetrapeptides moderate reactivity. Also, chemical applications were executed toward nailing tyrosine other via maleimide linker intramolecular hydroarylation to produce tyrosine-centered stapled products succinimide-glued macrocyclized products, respectively.

Language: Английский

Citations

4
Mono and di ortho-C–H acetoxylation of 2-aryloxyquinoline-3-carbaldehydes DOI Creative Commons
Manickam Bakthadoss, Oluwafemi S. Aina,

Tadiparthi Thirupathi Reddy

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(19), P. 13306 - 13310

Published: Jan. 1, 2024

A novel protocol for introducing an acetoxy functional group selectively on the ortho aryl sp 2 carbon of 2-aryloxyquinoline-3-carbaldehydes in good yields with tolerance using a palladium catalyst was developed first time.

Language: Английский

Citations

1
Iridium-catalyzed diacylmethylation of tyrosines and its peptides with sulfoxonium ylides DOI Creative Commons

Narendra Dinkar Kharat,

Sushma Naharwal,

Siva S. Panda

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(59), P. 7622 - 7625

Published: Jan. 1, 2024

Pyridyloxy-directed Ir( iii )-catalyzed diacylmethylation of protected tyrosines was achieved with alkyl and (hetero)aryl sulfoxonium ylides, furnishing tyrosine-based unnatural amino acids in good yields.

Language: Английский

Citations

0
Acetoxylation of Tyrosine-Containing Peptides Using a Palladium Catalyst DOI
Hisashi Yamamoto,

An Wu

Synfacts, Journal Year: 2023, Volume and Issue: 19(04), P. 0421 - 0421

Published: March 17, 2023

Key words palladium catalysis - C–H activation tyrosine acetoxylation

Language: Английский

Citations

0
Ruthenium(II)‐Catalyzed Selective C(sp2)−H Acyloxylation of 2‐Aroyl‐Pyridine Derivatives with Sodium Carboxylate DOI
Wenbo Ma, Tao Zheng, Linghui Gu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(3), P. 518 - 525

Published: Dec. 29, 2023

Abstract A ruthenium‐catalyzed C( sp 2 )−H acyloxylation of 2‐aroyl pyridine derivatives with simple sodium carboxylate utilizing transformable directing groups is described. This protocol features broad functional group tolerance and chemo‐ regio‐selectivity, providing the products in 45%‐84%yield. Furthermore, synthetic utility this was demonstrated by late‐stage functionalization pharmaceutical compounds. Notably, could be further transformed into a variety useful heterocycles under mild conditions.

Language: Английский

Citations

0