Direct meta‐C−H Perfluoroalkenylation of Arenes Enabled by a Cleavable Pyrimidine‐Based Template DOI

Massimo Brochetta,

Tania Borsari,

Sukdev Bag

et al.

Chemistry - A European Journal, Journal Year: 2019, Volume and Issue: 25(44), P. 10323 - 10327

Published: June 19, 2019

Abstract The development of efficient and mild methods for the synthesis organofluorine compounds is foremost interest in various fields chemistry. A direct pyrimidine‐based selective meta ‐C−H perfluoroalkenylation arenes involving several commercially available perfluoroolefins described. synthetic versatility protocol demonstrated by an extensive substrate scope including different benzylsulfonyl, alkylarene phenylacetic acid scaffolds. generality this methodology Ibuprofen, facile cleavage directing group gram‐scale reactions are presented.

Language: Английский

Late-stage C–H functionalization offers new opportunities in drug discovery DOI
Lucas Guillemard, Nikolaos Kaplaneris, Lutz Ackermann

et al.

Nature Reviews Chemistry, Journal Year: 2021, Volume and Issue: 5(8), P. 522 - 545

Published: July 13, 2021

Language: Английский

Citations

587

Stapled Helical Peptides Bearing Different Anchoring Residues DOI
Xiang Li, Si Chen, Weidong Zhang

et al.

Chemical Reviews, Journal Year: 2020, Volume and Issue: 120(18), P. 10079 - 10144

Published: Aug. 14, 2020

A large proportion of protein–protein interactions (PPIs) occur between a short peptide and globular protein domain; the peptides involved in surface play important roles, there is great promise for using motifs to interfere with interactions. Peptide inhibitors show more blocking compared small molecule inhibitors. However, have drawbacks including poor stability against circulating proteolytic enzymes an intrinsic inability penetrate cell membranes. Stapled helical peptides, by adopting preformed, stable α-helical conformation, exhibit improved membrane permeability linear bioactive peptides. In this review, we summarize broad aspects stapling chemistry, biophysics, biological applications specifically highlight methodology providing inventory different anchoring residues categorized into two natural amino acids, nonnatural or combination acids. Additional advantages specific techniques, but not limited reversibility, bio-orthogonal reactivity, photoisomerization, are also discussed individually. This review expected provide reference rational design druggable stapled targeting therapeutic proteins, particularly those PPIs, considering impact residues, functional cross-linkers, physical staple length, components, motif on biophysical properties

Language: Английский

Citations

204

Visible‐Light‐Promoted C(sp3)−H Alkylation by Intermolecular Charge Transfer: Preparation of Unnatural α‐Amino Acids and Late‐Stage Modification of Peptides DOI
Chao Wang,

Rupeng Qi,

Hongxiang Xue

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(19), P. 7461 - 7466

Published: Feb. 20, 2020

Disclosed herein is the visible-light-promoted deaminative C(sp3 )-H alkylation of glycine and peptides using Katritzky salts as electrophiles. Simple reaction conditions excellent functional-group tolerance provide a general strategy for efficient preparation unnatural α-amino acids precise modification with α-amino-acid residues. Mechanistic studies suggest that intermolecular charge transfer within glycine-Katritzky salt electron donor-acceptor (EDA) complex induces single-electron process without assistance photocatalyst.

Language: Английский

Citations

157

Electrochemical Late-Stage Functionalization DOI Creative Commons
Yulei Wang, Suman Dana, Hao Long

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(19), P. 11269 - 11335

Published: Sept. 26, 2023

Late-stage functionalization (LSF) constitutes a powerful strategy for the assembly or diversification of novel molecular entities with improved physicochemical biological activities. LSF can thus greatly accelerate development medicinally relevant compounds, crop protecting agents, and functional materials. Electrochemical synthesis has emerged as an environmentally friendly platform transformation organic compounds. Over past decade, electrochemical late-stage (eLSF) gained major momentum, which is summarized herein up to February 2023.

Language: Английский

Citations

141

Recent advances in chemical protein synthesis: method developments and biological applications DOI
Suwei Dong, Ji‐Shen Zheng, Yiming Li

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(4), P. 1060 - 1096

Published: March 12, 2024

Language: Английский

Citations

62

Tryptophan-specific modification and diversification of peptides and proteins DOI
S K Kundu, A. Bandyopadhyay, Rajib Sarkar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review provides an account of the tryptophan-specific conjugation peptides and proteins its extensive application in imaging living cells, radiolabelling proteins, protein engineering, etc .

Language: Английский

Citations

2

Peptide macrocyclization by transition metal catalysis DOI
Daniel G. Rivera, Gerardo M. Ojeda‐Carralero, Leslie Reguera

et al.

Chemical Society Reviews, Journal Year: 2020, Volume and Issue: 49(7), P. 2039 - 2059

Published: Jan. 1, 2020

Peptide macrocyclization continues expanding with the development of novel transition metal-catalyzed reactions capable both introducing conformational constraints and generating diversity at ring-closing moiety.

Language: Английский

Citations

106

Mangana(iii/iv)electro-catalyzed C(sp3)–H azidation DOI Creative Commons
Tjark H. Meyer, Ramesh C. Samanta, Antonio Del Vecchio

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 12(8), P. 2890 - 2897

Published: Dec. 28, 2020

The merger of manganese-catalyzed C–H functionalization with electrosynthesis enabled C(sp 3 )–H azidation devoid chemical oxidants or photochemical irradiation. Detailed mechanistic studies are supportive a manganese( iii/iv ) electrocatalysis.

Language: Английский

Citations

91

Late-stage C(sp2)–H and C(sp3)–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling DOI Creative Commons
Jun Wu, Nikolaos Kaplaneris, Shao‐Fei Ni

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(25), P. 6521 - 6526

Published: Jan. 1, 2020

C–H glycosylations of complex amino acids and peptides were accomplished through the assistance triazole peptide-isosteres. The palladium-catalyzed glycosylation provided access to C-glycosides fluorescent-labeled glycoamino acids.

Language: Английский

Citations

89

Chemodivergent manganese-catalyzed C–H activation: modular synthesis of fluorogenic probes DOI Creative Commons
Nikolaos Kaplaneris, Jongwoo Son, Lorena Mendive‐Tapia

et al.

Nature Communications, Journal Year: 2021, Volume and Issue: 12(1)

Published: June 7, 2021

Abstract Bioorthogonal late-stage diversification of amino acids and peptides bears enormous potential for drug discovery molecular imaging. Despite major accomplishments, these strategies largely rely on traditional, lengthy prefunctionalization methods, heavily involving precious transition-metal catalysis. Herein, we report a resource-economical manganese(I)-catalyzed C–H fluorescent labeling structurally complex ensured by direct alkynylation alkenylation manifolds. This modular strategy sets the stage unraveling structure-activity relationships between discrete fluorophores towards rational design BODIPY fluorogenic probes real-time analysis immune cell function.

Language: Английский

Citations

77