Unraveling the Cleavage Reaction of Hydroxylamines with Cyclopropenones Considering Biocompatibility DOI

Tianying Zeng,

Qian Wu, Yongjie Liu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 11, 2024

We develop a latent biocompatible cleavage reaction involving the hitherto unexplored interaction between hydroxylamines and cyclopropenones. Our study addresses regioselectivity challenges commonly observed in asymmetric cyclopropenone transformations, substantiated by variations substrate, Density Functional Theory calculations,

Language: Английский

Expedient Access to Polysubstituted Acrylamides via Strain-Release-Driven Dual Phosphine and Palladium Catalysis DOI

Yuxiang Yao,

Jing Zhang,

Xuehong Min

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(51), P. 6532 - 6535

Published: Jan. 1, 2024

Polysubstituted acrylamides are ubiquitous in bioactive molecules and natural products. However, synthetic methods for the assembly of these important motifs remain underdeveloped. Herein, we report expedient synthesis structurally diverse synthetically challenging polysubstituted from readily available aromatic amines, cyclopropenones (CpOs), aryl halides

Language: Английский

Citations

0

Bioorthogonal cyclopropenones for investigating RNA structure DOI Creative Commons
Wen Chen,

Christopher D. Sibley,

Brandon Latifi

et al.

bioRxiv (Cold Spring Harbor Laboratory), Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 24, 2024

Abstract RNA sequences encode secondary and tertiary structures that impact protein production other cellular processes. Misfolded RNAs can also potentiate disease, but the complete picture is lacking. To establish more comprehensive accurate structure-function relationships, new methods are needed to interrogate trap native conformations in environments. Existing tools primarily rely on electrophiles constitutively “on” or triggered by UV light, often resulting high background reactivity. We developed an alternative, chemically approach crosslink using bioorthogonal cyclopropenones (CpOs). These reagents selectively react with phosphines provide ketenes—electrophiles neighboring nucleophiles forge covalent crosslinks. As proof-of-concept, we synthesized a panel of CpOs appended them thiazole orange (TO-1). The TO-1 conjugates bound model aptamer (Mango) nanomolar affinity, confirmed fluorescence turn-on. After phosphine administration, crosslinks were formed between CpO probes RNA. degree crosslinking was both time dose-dependent. further applied biologically relevant conditions. Collectively, this work expands toolkit for studying its conformations.

Language: Английский

Citations

0

Autocatalysis‐Integrated Bioorthogonal (Poly)Catalyst‐Linked Immunosorbent Assay for Living Cell Membrane Antigens DOI

Xuepu Feng,

Guoming Tong, Z. Y. Ran

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract Immunoassay methods, notably enzyme‐linked immunosorbent assays (ELISAs), renowned for their signal amplification capabilities, are extensively employed in scientific research and clinical diagnostics. However, the instability of enzymes sensitivity to cellular environments present significant challenges broad application ELISA living cells. In this work, we a bioorthogonal (poly)catalysis‐linked assay (BCLISA) designed detection cell membrane antigens, which involves coupling catalysts based on small molecules or polymers antibodies. After screening, opted copper(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC) as core reaction system. The polymer‐based exhibit enhanced reactivity at same molecular concentration due multiple catalytic sites. Polytriazoles formed during CuAAC have ability chelate Cu(I), thereby promoting faster catalysis. By harnessing autocatalytic feature, successfully increased potential BCLISA. Ultimately, autocatalysis‐integrated BCLISA technique was antigen imaging both vitro membranes. This approach offers new method low‐abundance antigens

Language: Английский

Citations

0

Autocatalysis‐Integrated Bioorthogonal (Poly)Catalyst‐Linked Immunosorbent Assay for Living Cell Membrane Antigens DOI

Xuepu Feng,

Guoming Tong,

Zengwei Ran

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract Immunoassay methods, notably enzyme‐linked immunosorbent assays (ELISAs), renowned for their signal amplification capabilities, are extensively employed in scientific research and clinical diagnostics. However, the instability of enzymes sensitivity to cellular environments present significant challenges broad application ELISA living cells. In this work, we a bioorthogonal (poly)catalysis‐linked assay (BCLISA) designed detection cell membrane antigens, which involves coupling catalysts based on small molecules or polymers antibodies. After screening, opted copper(I)‐catalyzed azide‐alkyne cycloaddition (CuAAC) as core reaction system. The polymer‐based exhibit enhanced reactivity at same molecular concentration due multiple catalytic sites. Polytriazoles formed during CuAAC have ability chelate Cu(I), thereby promoting faster catalysis. By harnessing autocatalytic feature, successfully increased potential BCLISA. Ultimately, autocatalysis‐integrated BCLISA technique was antigen imaging both vitro membranes. This approach offers new method low‐abundance antigens

Language: Английский

Citations

0

Unraveling the Cleavage Reaction of Hydroxylamines with Cyclopropenones Considering Biocompatibility DOI

Tianying Zeng,

Qian Wu, Yongjie Liu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 11, 2024

We develop a latent biocompatible cleavage reaction involving the hitherto unexplored interaction between hydroxylamines and cyclopropenones. Our study addresses regioselectivity challenges commonly observed in asymmetric cyclopropenone transformations, substantiated by variations substrate, Density Functional Theory calculations,

Language: Английский

Citations

0