Discovery of Staircase Chirality through the Design of Unnatural Amino Acid Derivatives DOI Creative Commons

Anis Ur Rahman,

Yu Wang, Ting Xu

и другие.

Research, Год журнала: 2024, Номер 7

Опубликована: Янв. 1, 2024

Chirality has garnered significant attention in the scientific community since its discovery by Louis Pasteur over a century ago. It been showing profound impact on chemical, biomedical, and materials sciences. Significant progress made controlling molecular chirality, as evidenced several Nobel Prizes chemistry awarded this area, particularly for advancements asymmetric catalytic synthesis of molecules with central axial chirality. However, exploration new types chirality largely stagnant more than half century, likely due to complexity challenges inherent field. In work, we present novel type chirality—staircase inspired design unnatural amino acid derivatives. The architecture staircase is characterized 2 symmetrical phenyl rings anchored naphthyl pier, asymmetrically displaced influence chiral auxiliaries at their para positions. This unique framework thoroughly using spectroscopic techniques, absolute configuration definitively confirmed x-ray diffraction analysis. Remarkably, one exhibits 4 distinct chirality: central, orientational, turbo, combination that not previously documented literature. Computational studies density functional theory (DFT) calculations were conducted analyze relative energies individual isomers, results are agreement our experimental findings. We believe will open up research frontier catalysis, potential make substantial fields chemistry, medicine, science.

Язык: Английский

Carbene-catalyzed Phthalide Ether Functionalization for Discovering Chiral Phytovirucides that Specifically Targets Viral Nia Protein to Inhibit Proliferation DOI Creative Commons
Xiaoyi Wang, Weijia Yang, Shang Wu

и другие.

Research, Год журнала: 2025, Номер 8

Опубликована: Янв. 1, 2025

Plant diseases caused by vegetable viruses are an important threat to global food security, presenting a major challenge for the development of antiviral agrochemicals. Functional proteins plant play crucial role in viral life cycle, and targeted inhibition these has emerged as promising strategy. However, current discovery small molecules is hampered limitations synthetic approaches narrow range targets. Herein, we report practical application organocatalysis serving pesticide that bears unique molecular basis. An N -heterocyclic carbene-modulated reaction first designed asymmetrically functionalize diverse natural phenols with phthalides. Our method capable producing series new phthalidyl ethers under mild conditions good yields, enantioselectivity, functional group tolerance. Among these, compound ( R )- 3w exhibits excellent enantioselectivity-preferred curative activity against potato virus Y (PVY). Mechanistically, it proposed interacts nuclear inclusion body A (Nia) protein PVY at His150 residue. This binding impairs Nia’s function cleavage polyprotein, thereby inhibiting formation replication complex. The study provides insights into advancing protocol facilitate agrochemical discovery, our identified may serve potential lead future research PVY-Nia inhibitors.

Язык: Английский

Процитировано

1
Enantiopure Turbo Chirality Targets in Tri-Propeller Blades: Design, Asymmetric Synthesis, and Computational Analysis DOI Creative Commons
Yu Wang, Xu Ting, Ankit Pandey

и другие.

Molecules, Год журнала: 2025, Номер 30(3), С. 603 - 603

Опубликована: Янв. 29, 2025

Enantiopure turbo chirality in small organic molecules, without other chiral elements, is a fascinating topic that has garnered significant interest within the chemical and materials science community. However, further research into application of this concept have been severely limited by lack effective asymmetric tools. To date, only few enantiomers targets isolated, these were obtained through physical separation using HPLC, typically on milligram scales. In work, we report first approach to enantiopure absence elements such as central axial chirality. This demonstrated assembling aromatic phosphine oxides, where three propeller-like groups are anchored P(O) center via axes. Asymmetric induction was successfully carried out sulfonimine auxiliary, with absolute configurations conformations unambiguously determined X-ray diffraction analysis. The resulting frameworks exhibit propellers arranged either clockwise (P,P,P) or counterclockwise (M,M,M) configuration. arrangements, bulkier sides rings oriented toward oxygen atom P=O bond rather than opposite direction. Additionally, orientational configuration controlled auxiliary well, showing one Naph pushed away from group (-CH2-NHSO2-tBu) phenyl ring. Computational studies conducted relative energies for rotational barriers target along axis transition pathway between two enantiomers, meeting our expectations. work expected impact fields chemistry, biomedicine, future.

Язык: Английский

Процитировано

0
Exploring chiral and achiral properties of novel multilayer 3D polymers: synthesis and characterization DOI Creative Commons
Sai Zhang, Qingzheng Xu,

Xiuyuan Qin

и другие.

RSC Advances, Год журнала: 2025, Номер 15(5), С. 3227 - 3236

Опубликована: Янв. 1, 2025

This study reports the novel synthesis of multilayered 3D polymers via 1,3,5-position coupling 1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene with 1,8-dibronaphthalene, a previously unreported method.

Язык: Английский

Процитировано

0
Synthesis of vinyl, alkyl-substituted chiral acrylates via Krische iridium complex-catalysed allylic phosphonation DOI
Yuanyuan Zhang, Yi Deng, Kun Wei

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An enantioselective preparation of vinyl, alkyl-substituted chiral α-stereogenic acrylates is reported using two consecutive steps Ir-catalysed allylic alkylation aliphatic acetates with phosphonates and HWE olefination.

Язык: Английский

Процитировано

0
Characterization of Chiral Thiophene Multilayer 3D Polymers with AIE Properties for Environmental Monitoring of Chromium Ions DOI
Sai Zhang, Qingzheng Xu,

Qingkai Yuan

и другие.

Macromolecular Rapid Communications, Год журнала: 2025, Номер unknown

Опубликована: Апрель 14, 2025

Abstract This study reports the synthesis and characterization of novel thiophene‐based multilayer 3D chiral polymers incorporating methoxy octyloxy functional groups. These exhibit unique fluorescence properties, including a pronounced aggregation‐induced emission (AIE) phenomenon at lower excitation wavelength than previously reported thiophene systems. Additionally, demonstrate remarkable sensitivity in detecting hexavalent chromium ions (Cr 6+ ), significant environmental pollutant. The interaction between Cr leads to measurable changes fluorescence, highlighting their potential for applications monitoring biosensing. Importantly, these are effective actual water, where they maintain selectivity despite presence competing metal ions. enhanced further underscores suitability real‐world applications. work contributes field emphasizes versatility advanced sensing

Язык: Английский

Процитировано

0
Discovery of Staircase Chirality through the Design of Unnatural Amino Acid Derivatives DOI Creative Commons

Anis Ur Rahman,

Yu Wang, Ting Xu

и другие.

Research, Год журнала: 2024, Номер 7

Опубликована: Янв. 1, 2024

Chirality has garnered significant attention in the scientific community since its discovery by Louis Pasteur over a century ago. It been showing profound impact on chemical, biomedical, and materials sciences. Significant progress made controlling molecular chirality, as evidenced several Nobel Prizes chemistry awarded this area, particularly for advancements asymmetric catalytic synthesis of molecules with central axial chirality. However, exploration new types chirality largely stagnant more than half century, likely due to complexity challenges inherent field. In work, we present novel type chirality—staircase inspired design unnatural amino acid derivatives. The architecture staircase is characterized 2 symmetrical phenyl rings anchored naphthyl pier, asymmetrically displaced influence chiral auxiliaries at their para positions. This unique framework thoroughly using spectroscopic techniques, absolute configuration definitively confirmed x-ray diffraction analysis. Remarkably, one exhibits 4 distinct chirality: central, orientational, turbo, combination that not previously documented literature. Computational studies density functional theory (DFT) calculations were conducted analyze relative energies individual isomers, results are agreement our experimental findings. We believe will open up research frontier catalysis, potential make substantial fields chemistry, medicine, science.

Язык: Английский

Процитировано

2