Iterative click reactions using trivalent platforms for sequential molecular assembly DOI Creative Commons

Gaku Orimoto,

Suguru Yoshida

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(45), P. 5824 - 5827

Published: Jan. 1, 2024

A facile synthesis of multi(triazole)s by iterative click reactions is disclosed. Diverse multi(triazole)-type mid-molecules can be synthesized easily from readily available modules through good chemoselective reactions.

Language: Английский

Engineered Polymeric Microspheres with Synergistic Hydrogen‐Bonding Nanotraps and Multisite Adsorption for Ultrafast Herbicide Decontamination DOI Open Access

Jicai Jiang,

Haibo Wan,

Jinchang Zhang

et al.

Angewandte Chemie, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

Abstract The ultrafast removal of trace herbicides like paraquat (PQ) and diquat (DQ) from water is urgent yet challenging due to their highwater stability strong‐binding properties. Here, efficient PQ DQ based on hydrogen‐bonding nanotraps dominant multisite adsorption were developed. Two crosslinked polymeric microspheres, β CD‐PF γ CD‐PF, synthesized cyclodextrins (CDs) hexafluorocyclotriphosphazene (HFP). microsphere with sufficient the pore surface prompts kinetics constants up 127.09 192.64 g mg −1 min , achieving 99% efficiency for within 5 s. exhibits exceptional selectivity over larger competing dyes. Importantly, (1 ppm) can be effectively treated achieve a concentration far below US Environmental Protection Agency (EPA) standard (0.003 30 driven by mechanism: electrostatic π–π interactions HFP promote adsorbate accumulation CD surface, while high‐density in enhance hydrogen bond strength, enabling rapid capture. This work provides valuable strategy designing adsorbents effective herbicide water.

Language: Английский

Citations

0

The certainty of a few good reactions DOI Creative Commons

Adam D. Moorhouse,

Joshua A. Homer, John E. Moses

et al.

Chem, Journal Year: 2023, Volume and Issue: 9(8), P. 2063 - 2077

Published: April 19, 2023

Language: Английский

Citations

9

Poison to promise: The resurgence of organophosphorus fluoride chemistry DOI

William P. Chappell,

Natalie Schur,

James A. Vogel

et al.

Chem, Journal Year: 2024, Volume and Issue: 10(6), P. 1644 - 1654

Published: May 9, 2024

Language: Английский

Citations

3

Arginine Accelerates Sulfur Fluoride Exchange and Phosphorus Fluoride Exchange Reactions between Proteins DOI Creative Commons
Li Cao, Bingchen Yu, Paul C. Klauser

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(47)

Published: Aug. 8, 2024

Sulfur fluoride exchange (SuFEx) and phosphorus (PFEx) click chemistries are advancing research across multiple disciplines. By genetically incorporating latent bioreactive unnatural amino acids (Uaas), these have been integrated into proteins, enabling precise covalent linkages with biological macromolecules paving the way for new applications. However, their suboptimal reaction rates in proteins limit effectiveness, traditional catalytic methods small molecules often incompatible systems or vivo We demonstrated that introducing an arginine adjacent to Uaa significantly boosts SuFEx PFEx between proteins. This method is effective various Uaas, target residues, protein environments. Notably, it also enables efficient reactions acidic conditions, common certain cellular compartments tumor microenvironments, which typically hinder reactions. Furthermore, we developed first cell engager substantially enhances natural killer activation through improved interaction facilitated by arginine. These findings provide mechanistic insights offer a biocompatible strategy harness robust developing biotherapeutics.

Language: Английский

Citations

3

Computational analysis of modular diazotransfer reactions for the development of predictive reactivity models and diazotransfer reagents DOI

Meng-Meng Zheng,

Cai Liu,

Tiancheng Ma

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 10, 2024

Language: Английский

Citations

3

Ethene‐1,1‐disulfonyl Difluoride (EDSF) for SuFEx Click Chemistry: Synthesis of SuFExable 1,1‐Bissulfonylfluoride Substituted Cyclobutene Hubs DOI Creative Commons
Christopher J. Smedley, Marie‐Claire Giel, Thomas Fallon

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(30)

Published: May 24, 2023

We present the synthesis of 1,1-bis(fluorosulfonyl)-2-(pyridin-1-ium-1-yl)ethan-1-ide, a bench-stable precursor to ethene-1,1-disulfonyl difluoride (EDSF). The novel SuFEx reagent, EDSF, is demonstrated in preparation 26 unique 1,1-bissulfonylfluoride substituted cyclobutenes via cycloaddition reaction. regioselective click reaction rapid, straightforward, and highly efficient, enabling generation functionalized 4-membered ring (4MR) carbocycles. These carbocycles are valuable structural motifs found numerous bioactive natural products pharmaceutically relevant small molecules. Additionally, we showcase diversification cyclobutene cores through selective Cs

Language: Английский

Citations

8

Protocol for producing phosphoramidate using phosphorus fluoride exchange click chemistry DOI Creative Commons
Joshua A. Homer, Shoujun Sun, Rebecca A. Koelln

et al.

STAR Protocols, Journal Year: 2024, Volume and Issue: 5(1), P. 102824 - 102824

Published: Jan. 12, 2024

Phosphorus fluoride exchange (PFEx) is a catalytic click reaction that involves exchanging high oxidation state P-F bonds with alcohol and amine nucleophiles, reliably yielding P-O- P-N-linked compounds. Here, we describe steps for preparing phosphoramidic difluoride performing two sequential PFEx reactions to yield phosphoramidate through careful catalyst selection. We then detail procedures handling quenching potentially toxic P-F-containing compounds ensure user safety when conducting reactions. For complete details on the use execution of this protocol, please refer Sun et al.

Language: Английский

Citations

2

Single-Atom Ligation of Four Different Alcohols at One Silicon Center: Methodology Development and Proof of Concept DOI Creative Commons
Chao Wang, Xin Xu, Xinyu Zhang

et al.

Published: April 9, 2024

Click chemistry continues to impact the and biology community, with most well-known being CuAAC click chemistry. Topologically, only ligated two fragments in a two-dimensional manner. While SuFEx PFEx could ligate three-dimensionally, maximally three (amine/alcohol) be clicked together for now. Herein, we report three-dimensional single-atom ligation of four different (alcohols) at one silicon center using triphenylchlorosilane as hub an iterative, controllable, programmable fashion. To fulfill mission, established new silicon-phenyl exchange reaction alcohols. A broad spectrum alcohols various types phenylchlorosilanes hubs, affording library mixed-dialkoxysilanes, trialkoxysilanes, tetraalkoxysilanes. Notably, fully heteroleptic tetraalkoxysilanes were barely known literature extremely difficult access selective fashion from retrosynthetic viewpoint. Our protocol thus provided robust solution materials such nature. highlight application potential, biologically relevant alcohols, representing functions, successfully Si(IV) tetraalkoxysilane. More importantly, released recovered via silicon-alkoxy stable yet cleavable Si-O bonds.

Language: Английский

Citations

2

SO2F2-Mediated Fluorination of P(O)–H and P(O)–OH Compounds under Mild Conditions DOI
Guofu Zhang,

Linjun Han,

Chenfei Guan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13142 - 13148

Published: Sept. 1, 2023

With the increasing relevance of organophosphorus fluorine compounds in pharmaceutical industry, their synthesis has attracted great attention. Herein, we report an efficient fluorination strategy for P(O)–H and P(O)–OH using sulfuryl fluoride as reagent. Avoiding use expensive or complex prepreparation reagents fluoridation, this could conveniently construct a variety fluorophosphonates phosphonofluoridates under mild conditions without additional oxidants.

Language: Английский

Citations

5

Click Chemistry and Bioorthogonal Chemistry: General Consideration from Discovery to Applications DOI
Vinod K. Tiwari, Manoj K. Jaiswal, Sanchayita Rajkhowa

et al.

Materials horizons, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 42

Published: Jan. 1, 2024

Language: Английский

Citations

1