Late-Stage Radical C–H Alkylamination of Tyrosine Compounds and Phenol-Containing Drugs DOI
Paula Andrade‐Sampedro, Arkaitz Correa

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 3, 2024

A modular site-selective iron-catalyzed radical amination of a number phenol-containing biomolecules such as tyrosine-containing peptides, estrogens, and other phenol-based pharmaceuticals has been developed. The method features the use cost-efficient combination FeBr

Language: Английский

Photoredox-Catalyzed Oxidative C–H Alkylation of Glycine Derivatives with 4-Alkyl-1,4-dihydropyridines DOI

Madala Hari Babu,

Eunbin Jang, Jaehoon Sim

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(15), P. 2339 - 2346

Published: March 11, 2024

Abstract Oxidative α-C(sp3)–H alkylation of N-arylated glycine derivatives with 4-alkyldihydropyridine (alkyl-DHPs) as versatile alkyl radical precursors has been developed. Utilizing visible-light-driven photoredox catalysis and ammonium persulfate an oxidizing agent, this methodology facilitates the site-selective derivatives, enabling peptides. The reaction exhibits broad substrate scope, including various radicals acid-labile functional groups. This approach expands synthetic toolbox in peptide chemistry, offering a mild efficient method for synthesis modified

Language: Английский

Citations

3
Ozone treatment increase the whiteness of soy protein isolate through the degradation of isoflavone DOI
Junyou Li,

Yunqi Chen,

Dan Wang

et al.

Food Chemistry, Journal Year: 2024, Volume and Issue: 464, P. 141665 - 141665

Published: Oct. 17, 2024

Language: Английский

Citations

3
Experimental and Theoretical Investigation into Fluorescent Detection of Lysine Using a Flexible Pincer Probe DOI
Qiao Li

Published: Jan. 1, 2025

Language: Английский

Citations

0
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
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
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

2
Genetically Encoded Photocaged Proteinogenic and Non‐Proteinogenic Amino Acids DOI

Xiaochen Yang,

Xun‐Cheng Su,

Weimin Xuan

et al.

ChemBioChem, Journal Year: 2024, Volume and Issue: unknown

Published: June 4, 2024

Photocaged amino acids could be genetically encoded into proteins via genetic code expansion (GCE) and constitute unique tools for innovative protein engineering. There are a number of photocaged proteinogenic that allow strategic conversion their variants, thus enabling spatiotemporal non-invasive regulation functions using light. Meanwhile, there hand non-proteinogenic address the challenges in directly encoding certain non-canonical (ncAAs) structurally resemble ones or possess highly reactive functional groups. Herein, we would like to summarize efforts acids, hoping draw more attention this fruitful exciting scientific campaign.

Language: Английский

Citations

2
MnO4--triggered wavelength-changeable and rapid-response fluorescence sensor for paper-based on-site sensing of tyrosinase activity in potato DOI
Yifei Ma, Xiaoxue Liu,

Lihua Pang

et al.

Talanta, Journal Year: 2024, Volume and Issue: 282, P. 127021 - 127021

Published: Oct. 11, 2024

Language: Английский

Citations

2
Iron-Catalyzed Late-Stage Radical C–H Alkylamination of Phenol-Containing Drugs and Biomolecules DOI Creative Commons
Paula Andrade‐Sampedro, Arkaitz Correa

Published: May 10, 2024

A modular site-selective iron-catalyzed radical amination of a number phenol-containing biomolecules such as tyrosine-containing peptides, estrogens and other phenol-based pharmaceuticals has been developed. The method features the use cost-efficient combination FeBr3 catalyst along with triflic acid Brønsted acid, thereby enabling predictable appendance morpholine related heterocycles at ortho C–H bond phenols in late-stage fashion. This alkylamination technique leverages electron-rich nature to undergo oxidation corresponding phenoxyl radicals further coupling situ formed electrophilic aminium cation species.

Language: Английский

Citations

1
Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives DOI Creative Commons

Bo Dong,

Weiguan Qi,

Yifeng Chen

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 12(2)

Published: Nov. 21, 2024

Abstract Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular streamlined synthesis of a diverse library peptide‐related compounds. Particularly notable is their application in pharmaceutical development, leveraging site‐selective late‐stage functionalization. Here, visible light‐induced three‐component reaction involving arylthianthrenium salts, acid/peptide derivatives, alkenes are introduced. This approach utilizes captodatively‐stabilized carbon radicals to enable radical‐radical C─C coupling, effectively constructing complex molecules. method offers promising alternative route for peptide‐derived bio‐relevant compounds

Language: Английский

Citations

1