The inverse electron demand diels-alder (IEDDA): A facile bioorthogonal click reaction for development of injectable polysaccharide-based hydrogels for biomedical applications DOI
Lihua Yan, Zhenzhen Zhao, Yuqian Liu

et al.

Carbohydrate Polymers, Journal Year: 2024, Volume and Issue: 352, P. 123142 - 123142

Published: Dec. 16, 2024

Language: Английский

Copper-Catalyzed Intermolecular [2 + 2 + 2] Annulation of Diynes with Alkynes: Construction of Carbazoles DOI
Zhentao Zhang,

Chen Luo,

Zhiyong Yu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

Transition-metal-catalyzed [2 + 2 2] annulation of alkynes is an efficient pathway for the synthesis aromatic compounds. However, most established methods require noble metal catalysts. Herein, we report a copper-catalyzed intermolecular diynes with through vinyl cation intermediates, enabling atom-economical preparation biologically important carbazole skeletons. The reaction shows good regioselectivity in aryl(alkyl)alkynes. Moreover, preliminary results have also been obtained related catalytic atroposelective transformation. This represents rare example non-noble-metal-catalyzed ynamides pathway.

Language: Английский

Citations

1

Lewis acid-catalyzed (3+2) annulation of bicyclobutanes with ynamides: Access to 2-amino bicyclo[2.1.1]hexenes DOI Creative Commons

Deeptanu Sarkar,

Shiksha Deswal,

Rohan Chandra Das

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Strain-release driven annulations with bicyclo[1.1.0]butanes (BCBs) have become an attractive area of research for the synthesis bioisosteric bicyclohexane derivatives, which play a vital role in drug discovery. Interestingly, utilization inherent strain BCBs functionalized amino-bicyclo[2.1.1]hexenes, may spatially mimic substituted benzenes and anilines, has received only scant attention. Herein, we report Sc(OTf)

Language: Английский

Citations

7

Recent progress of chemical methods for lysine site-selective modification of peptides and proteins DOI
Jian Li, Jinjin Chen, Qi-Long Hu

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110126 - 110126

Published: June 1, 2024

Language: Английский

Citations

4

Peptide and Protein Cysteine Modification Enabled by Hydrosulfuration of Ynamide DOI Creative Commons
Changliu Wang, Zhenguang Zhao,

Reem Ghadir

et al.

ACS Central Science, Journal Year: 2024, Volume and Issue: 10(9), P. 1742 - 1754

Published: Aug. 21, 2024

Efficient functionalization of peptides and proteins has widespread applications in chemical biology drug discovery. However, the chemoselective site-selective modification remains a daunting task. Herein, highly efficient chemo-, regio-, stereoselective hydrosulfuration ynamide was identified as an method for precise by uniquely targeting thiol group cysteine (Cys) residues. This novel could be facilely operated aqueous buffer fully compatible with wide range proteins, including small model large full-length antibodies, without compromising their integrity functions. Importantly, this reaction provides Z-isomer corresponding conjugates exclusively superior stability, offering approach to peptide protein therapeutics. The potential application further exemplified Cys-bioconjugation variety ynamide-bearing functional molecules such molecule drugs, fluorescent/affinity tags, PEG polymers. It also proved redox proteomic analysis through Cys-alkenylation. Overall, study bioorthogonal tool Cys-specific functionalization, which will find broad synthesis peptide/protein conjugates.

Language: Английский

Citations

4

Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement DOI

Ji‐Jia Zhou,

Li‐Gao Liu, Zhentao Zhang

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110870 - 110870

Published: Jan. 1, 2025

Language: Английский

Citations

0

Chiral Phosphoric Acid-Catalyzed Kinetic Resolution of Tertiary Alcohol-Tethered Ynamides via Controllable Hydroalkoxylation DOI

Da-Qiu Cui,

Gan-Lu Qian,

Hongxing Zheng

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 2424 - 2433

Published: Jan. 27, 2025

Language: Английский

Citations

0

Isoxazoles as efficient alkyne amination reagents in divergent heterocycle synthesis DOI Creative Commons
Xiao-Kang Zhu, Zhe Meng, Bo Zhou

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review summarizes the latest trends and developments of isoxazole-enabled alkyne amination reactions their applications in divergent heterocycle synthesis.

Language: Английский

Citations

0

Copper-Catalyzed Triyne Cyclization via Vinyl Cations DOI
Chen Luo,

Yan-Xin Zheng,

Sheng-Biao Ji

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Herein, we describe an efficient copper-catalyzed cyclization of triynes via vinyl cation intermediates. The reaction leads to the practical and atom-economical synthesis valuable polycyclic pyrroles by constructing three new rings in one step under mild conditions. proposed mechanism shows ordered regioselective alkynes. Moreover, possibility such asymmetric triyne also emerges.

Language: Английский

Citations

0

Copper-Catalyzed and 1,3-Sulfonyl Migration Enabled Installation of Azaindoles in the Periphery of Aryl Rings: Synthesis of Sulfonylated Pyrrolo[2,3-b]quinolines and Investigation of Antimalarial Potency DOI
Shivani Choudhary,

Gayyur,

Siddhant

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 24, 2025

Herein, an atom efficient and one-pot protocol, offering a series of sulfonylated pyrrolo[2,3-b]quinolines via C-N, C-C, C-S bond formation, has been developed with inexpensive copper catalyst. Notably, the reaction proceeds double-annulation followed by 1,3-sulfonyl migration sequence. Moreover, method is applicable to broad range 2-carbonylanilines. Furthermore, synthetic applications scale-up highlight utility potential this protocol. In addition, antimalarial property showed parasite inhibition without cytotoxic effects in mammalian cells.

Language: Английский

Citations

0

N‐ to C‐Peptide Synthesis, Arguably the Future for Sustainable Production DOI Creative Commons

Kinshuk Ghosh,

William D. Lubell

Journal of Peptide Science, Journal Year: 2025, Volume and Issue: 31(6)

Published: May 1, 2025

A revolution in peptide production arrived from the innovation of carboxylate to amine C- N-direction solid-phase synthesis. This cornerstone modern science has enabled multiple academic and industrial applications; however, process N-solid phase synthesis (C-N-SPPS) extreme mass intensity poor atom economy. Notably, C-N-SPPS relies upon use atom-intensive protecting groups, such as fluorenylmethyloxycarbonyl (Fmoc) protection wasteful excess protected amino acids coupling agents. On other hand, N- C-direction offers potential minimize may arguably enable more efficient means for manufacturing peptides. For example, amide bond formation been accomplished using methods employing thioesters, vinyl esters, transamidation achieve with minimal epimerization. review aims provide an overview C-peptide indicating advantages taking this avenue sustainable production.

Language: Английский

Citations

0