Lewis Acid Promotes Three-Component Cyclization to Construct Dithioxazole Derivatives DOI
Kai Zou,

Anquan Li,

Yitong Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 16, 2024

A simple and effective strategy for the construction of disulfide-substituted oxazole derivatives from amides, ynals, acetyl disulfides via a Lewis acid-promoted three-component reaction has been reported. In addition, this possesses other unique advantages, such as transition-metal-free catalysis, production disulfides, good functional group tolerance, regioselectivity.

Language: Английский

Mechanical Regulation of Polymer Gels DOI
Chenggong Xu,

Yi Chen,

Siyang Zhao

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(18), P. 10435 - 10508

Published: Sept. 16, 2024

The mechanical properties of polymer gels devote to emerging devices and machines in fields such as biomedical engineering, flexible bioelectronics, biomimetic actuators, energy harvesters. Coupling network architectures interactions has been explored regulate supportive characteristics gels; however, systematic reviews correlating mechanics interaction forces at the molecular structural levels remain absent field. This review highlights engineering gel a comprehensive mechanistic understanding regulation. Molecular alters architecture manipulates functional groups/moieties level, introducing various permanent or reversible dynamic bonds dissipative energy. usually uses monomers, cross-linkers, chains, other additives. Structural utilizes casting methods, solvent phase regulation, mechanochemistry, macromolecule chemical reactions, biomanufacturing technology construct tailor topological structures, heterogeneous modulus compositions. We envision that perfect combination may provide fresh view extend exciting new perspectives this burgeoning also summarizes recent representative applications with excellent properties. Conclusions are provided from five aspects concise summary, mechanism, biofabrication upgraded applications, synergistic methodology.

Language: Английский

Citations

13
Non-symmetric stapling of native peptides DOI
Fa‐Jie Chen, Wanzhen Lin, Fen‐Er Chen

et al.

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(5), P. 304 - 318

Published: April 4, 2024

Language: Английский

Citations

8
Recent advances in peptide macrocyclization strategies DOI Creative Commons

Pengyuan Fang,

W. PANG,

Shouhu Xuan

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Owing to their special spatial structures, peptide-based macrocycles have recently shown tremendous promise in multidisciplinary research ranging from potent antibiotics against resistant strains functional biomaterials with novel properties.

Language: Английский

Citations

6
Stabilized Carbon‐Centered Radical‐Mediated Carbosulfenylation of Styrenes: Modular Synthesis of Sulfur‐Containing Glycine and Peptide Derivatives DOI Creative Commons
Zihui Yang, Jia Liu, Lan‐Gui Xie

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 11(29)

Published: June 9, 2024

Abstract Sulfur‐containing amino acids and peptides play critical roles in organisms. Thiol‐ene reactions between the thiol residues of L ‐cysteine alkenyl fragments designed coupling partners serve as primary tools for constructing C─S bonds synthesis unnatural sulfur‐containing acid derivatives. These are favored due to preference hydrogen transfer from β‐sulfanyl carbon radical intermediates. In this paper, study proposes utilizing carbon‐centered radicals stabilized by capto‐dative effect, generated under photocatalytic conditions N –aryl glycine The aim is compete with hydrogen, enabling C─C bond formation radicals. This protocol robust presence air water, offers significant potential a modular efficient platform synthesizing modifying peptides, particularly abundant disulfides styrenes.

Language: Английский

Citations

5
Direct C−H Sulfuration: Synthesis of Disulfides, Dithiocarbamates, Xanthates, Thiocarbamates and Thiocarbonates DOI
Qiao Sun, Yuan Xu,

Liu Yang

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(9)

Published: Feb. 29, 2024

Abstract In light of the important biological activities and widespread applications organic disulfides, dithiocarbamates, xanthates, thiocarbamates thiocarbonates, continual persuit efficient methods for their synthesis remains crucial. Traditionally, preparation such compounds heavily relied on intricate multi‐step syntheses use highly prefunctionalized starting materials. Over past two decades, direct sulfuration C−H bonds has evolved into a straightforward, atom‐ step‐economical method organosulfur compounds. This review aims to provide an up‐to‐date discussion disulfuration, dithiocarbamation, xanthylation, thiocarbamation thiocarbonation, with special focus describing scopes mechanistic aspects. Moreover, synthetic limitations some these methodologies, along key unsolved challenges be addressed in future are also discussed. The majority examples covered this accomplished via metal‐free, photochemical or electrochemical approaches, which alignment overraching objectives green sustainable chemistry. comprehensive consolidate recent advancements, providing valuable insights dynamic landscape strategies crucial classes

Language: Английский

Citations

4
Redox-Regulated and Guest-Driven Transformations of Aromatic Oligoamide Foldamers in Advanced Structures DOI
Lu Yu, Dongyao Li, Chunmiao Ma

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(19), P. 12907 - 12912

Published: May 1, 2024

In this study, we demonstrate that an aromatic oligoamide sequence assembles into a trimeric helix-turn-helix architecture with disulfide linkage, and upon cleavage of it reconstructs antiparallel double helix. The helix is accessible to encapsulate diacid guest within its cavity, forming 2:1 host–guest complex. contrast, hydrogen-bonding interactions between the trimeric-assembled structure guests induce conformational shift in helix, resulting cross-shaped double-helix complex at 2:2 ratio. Interconversions along their respective complexes, can be initiated through thiol/disulfide redox-mediated regulation.

Language: Английский

Citations

4
Recent Advances in Metal-Free Peptide Stapling Strategies DOI Creative Commons

Wanglin Zhan,

Hongliang Duan, Chengxi Li

et al.

Chem & Bio Engineering, Journal Year: 2024, Volume and Issue: 1(7), P. 593 - 605

Published: June 11, 2024

Protein–protein interactions (PPIs) pose challenges for intervention through small molecule drugs, protein and linear peptides due to inherent limitations such as inappropriate size, poor stability, limited membrane penetrance. The emergence of stapled α-helical presents a promising avenue potential competitors inhibiting PPIs, demonstrating enhanced structural stability increased tolerance proteolytic enzymes. This review aims provide an overview metal-free stapling strategies involving two identical natural amino acids, different non-natural multicomponent reactions. primary objective is delineate comprehensive peptide approaches foster innovative ideation among readers by accentuating methodologies published within the past five years elucidating evolving trends in peptides.

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
Phosphine-promoted Thiol-Specific Bioconjugation with Allylic Acetates DOI Creative Commons
Teck‐Peng Loh, Xiaohong Li, Tao Xu

et al.

Research Square (Research Square), Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

Abstract Thiol-specific modification of proteins through conjugation with small molecules represents a critical advancement in biological research and therapeutic development, particularly the context antibody-drug conjugates (ADCs) for targeted cancer therapy. Despite widespread use maleimide-based linkers, their stability under physiological conditions remains major limitation, often compromising efficacy. In this investigation, we developed novel efficient thiol-specific bioconjugation strategy that employs allylic acetate, activated by recyclable solid phosphine catalyst. This approach achieves high yields demonstrates robust bio-compatible, room-temperature conditions. Notably, it sets new record fastest cysteine-conjugation reaction rate reported to date, constant k2 = 1.49 × 106 M− 1s− 1. The method expands substrate scope introduces sustainable, environmentally friendly ADC linker design, offering significant creation stable, biocompatible, therapeutically effective compounds.

Language: Английский

Citations

0
SO2F2 mediated click chemistry enables modular disulfide formation in diverse reaction media DOI Creative Commons
Hengzhao Li, Mengqi Peng, Junyu Li

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Sept. 27, 2024

Language: Английский

Citations

1