Manganese(I)-Catalyzed C–H Allylation of Tryptophans and Their Oligopeptides On Water DOI
Fabrice Gallou, Lutz Ackermann, Julia Struwe

et al.

Synlett, Journal Year: 2024, Volume and Issue: 35(08), P. 903 - 907

Published: Feb. 14, 2024

Abstract The manganese(I)-catalyzed allylation of the amino acid tryptophan is realized under exceedingly mild conditions using water as a sustainable and non-hazardous reaction medium, instead classical organic solvents, with great potential for green chemistry. Synthetically useful α,β-unsaturated esters can be accessed by Morita–Baylis–Hillman (MBH) adducts following fast C–H activation approach. robustness this procedure reflected kinetic analysis at different temperatures reduced catalyst loadings are employed.

Language: Английский

Selenium‐Electrocatalytic Cyclization of 2‐Vinylanilides towards Indoles of Peptide Labeling DOI

Shaogao Zeng,

Songlin Fang,

Haiping Cai

et al.

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(20)

Published: Aug. 20, 2022

A novel selenium-electrocatalytic intramolecular cyclization of 2-vinylanilides for synthesis functionalized indoles and azaindoles has been developed. In contrast to the previous synthetic methods, this sustainable protocol enabled unparalleled broad substrates scope viable with highly functional sensitive groups by employing recyclable selenium catalyst, under mild, metal- external-oxidant-free conditions. The approach can be used late-stage modification complex bioactive molecular system, thereby setting stage versatile syntheses decorated peptide labeling. plausible catalytic pathway was proposed.

Language: Английский

Citations

17
Late-stage peptide labeling with near-infrared fluorogenic nitrobenzodiazoles by manganese-catalyzed C–H activation DOI Creative Commons
Tsuyoshi Oyama, Lorena Mendive‐Tapia,

Verity Cowell

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(21), P. 5728 - 5733

Published: Jan. 1, 2023

Late-stage diversification of structurally complex amino acids and peptides provides tremendous potential for drug discovery molecular imaging. Specifically, labeling with fluorescent tags is one the most important methods visualizing their mode operation. Despite major recent advances in field, direct peptide by C-H activation largely limited to dyes relatively short emission wavelengths, leading high background signals poor signal-to-noise ratios. In sharp contrast, here we report on catalyzed non-toxic manganese(i) via C(sp2)-H alkenylation chemo- site-selective manners, providing modular access novel near-infrared (NIR) nitrobenzodiazole-based fluorogenic probes.

Language: Английский

Citations

10
Designing Peptide-Based Nucleophilic Catalysts Possessing Multiple Identical Active Sites for Late-Stage Chlorination of Peptides and Drugs DOI

Subimal Patra,

Haripriyo Mondal,

Uttam Dash

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

In the quest for developing catalysts with multiple active sites, we designed a series of methionine-based peptide prepared by classical coupling. Given widespread presence aromatic chloro-substituents and their significant pharmacokinetic properties, performance these were evaluated late-stage chlorination tyrosine residue on peptides up to octamer as well drug molecules. The operationally simple reaction conditions, excellent catalyst loading 0.25 mol %, gram-scale reactions are major highlights this method.

Language: Английский

Citations

0
Ru‐Catalyzed C−H Hydroxylation of Tyrosine‐Containing Di‐ and Tripeptides toward the Assembly of L‐DOPA Derivatives DOI Creative Commons
Paula Andrade‐Sampedro, Jon M. Matxain, Arkaitz Correa

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(12), P. 2072 - 2079

Published: May 6, 2022

Abstract The development of catalytic tools for the late‐stage modification amino acids within a peptide framework is challenging task capital importance. Herein, we report Ru‐catalyzed C( sp 2 )−H hydroxylation collection Tyr‐containing di‐ and tripeptides featuring use carbamate as removable directing group PhI(OCOCF 3 ) (PIFA) oxidant. This air‐compatible tagging technique reliable, scalable provides access to L‐DOPA (L‐3,4‐dihydroxyphenylalanine) peptidomimetics in racemization‐free fashion. Density Functional Theory calculations support Ru(II)/Ru(IV) cycle. magnified image

Language: Английский

Citations

15
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
Pd‐Catalyzed Arylation and Benzylation of Tyrosine at the δ−C(sp2)−H and C(2) Positions: Expanding the Library of Unnatural Tyrosines DOI
Prabhakar Singh, Srinivasarao Arulananda Babu

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(31)

Published: June 20, 2023

Abstract This paper describes Pd(II)‐catalyzed picolinamide‐directed intermolecular arylation and benzylation of remote δ −C(sp 2 )−H bond (C(2) position) the aryl ring in tyrosine derivatives expansion library unnatural tyrosine. Various racemic enantiopure bis C(2) ( ortho C−H) arylated benzylated were assembled good yields. Removal picolinoyl moiety after C(2)−H assembling tyrosine‐based peptides using tyrosines shown. Tyrosine biaryl amino acids are vital scaffolds medicinal chemistry. Correspondingly, this work is a contribution towards with biaryl‐ or terphenyl diarylmethane‐based scaffolds.

Language: Английский

Citations

8
Electrochemistry-enabled residue-specific modification of peptides and proteins DOI
A. Bandyopadhyay,

Pranay Biswas,

S K Kundu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(6), P. 1085 - 1101

Published: Dec. 29, 2023

This review focuses on up-to-date developments of electrochemistry-promoted residue-specific modification peptides and proteins. Specific protocols for five redox-active amino acid residues, namely cysteine, tyrosine, tryptophan, histidine methionine, were explained in detail.

Language: Английский

Citations

7
Palladium‐Catalyzed Site‐Selective C(sp2)−H Acetoxylation of Tyrosine‐Containing Peptides DOI Creative Commons
Iñaki Urruzuno, Paula Andrade‐Sampedro, Arkaitz Correa

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 26(6)

Published: Dec. 27, 2022

Abstract A Pd‐catalyzed C(sp 2 )−H acetoxylation of Tyr‐containing peptides is described. The method relies on the use a removable 2‐pyridyloxy group as directing and distinguished by its reliable scalability easily tuned regioselectivity to perform mono‐ diacetoxylation reactions. Remarkably, assembly L–DOPA peptidomimetics beyond reach upon cleavage group.

Language: Английский

Citations

9
Ruthenium(II)-Catalyzed Sterically Hindered C–H Acyloxylation to Synthesize Biaryl Isoquinoline Derivatives via Peresters DOI
Hao Liu,

Wei Chi,

Lin Dong

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 3148 - 3158

Published: Feb. 22, 2023

A novel C-H acyloxylation method of 1-(1-naphthalen-1-yl)isoquinoline derivatives with peresters in the presence [Ru(p-cymene)Cl2]2 has been developed. The combination ruthenium(II), AgBF4, CoI2, and 2,2,6,6-tetramethyl-1-piperidinyloxy is found to be an effective catalytic system provide various biaryl compounds satisfactory yields within minutes. Notably, steric hindrance a very important determinant reaction.

Language: Английский

Citations

5