Complex Functional Systems with Three Different Types of Dynamic Covalent Bonds

Zhang, Kang‐Da; Matile, Stefan

doi:10.1002/ange.201503033

Cited by 21 publications

(3 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…10 The evolution of constitutional dynamic networks would allow access to structural diversity and emerging properties. Among elegant examples, three orthogonal DCRs (disulfide exchange, hydrazone exchange, and boronic ester exchange) were employed for programmed assembly of templated chromophores 11 and surface architectures, 12 respectively. In another case with thiols as shared inputs, exchanges of disulfide, thioester, and dithioacetal were able to selectively intercommunicate to achieve multilayer networks.…”

Section: ■ Introductionmentioning

confidence: 99%

Dynamic Covalent Switches and Communicating Networks for Tunable Multicolor Luminescent Systems and Vapor-Responsive Materials

Zou

Yun

et al. 2019

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Molecular switches are an intensive area of research, and in particular, the control of multistate switching is challenging. Herein we introduce a general and versatile strategy of dynamic covalent switches and communicating networks, wherein distinct states of reversible covalent systems can induce addressable fluorescence switching. The regulation of intramolecular ring/chain equilibrium, intermolecular dynamic covalent reactions (DCRs) with amines, and both permitted the activation of optical switches. The variation in electronwithdrawing competition between the fluorophore and 2formylbenzenesulfonyl unit afforded diverse signaling patterns. The combination of switches in situ further enabled the creation of communicating networks for multistate color switching, including white emission, through the delicate control of DCRs in complex mixtures. Finally, reversible and recyclable multiresponsive luminescent materials were achieved with molecular networks on the solid support, allowing visualization of different types of vapors and quantification of primary amine vapors with high sensitivity and wide detection range. The results reported herein should be appealing for future studies of dynamic assemblies, molecular sensing, intelligent materials, and biological labeling.

show abstract

Section: ■ Introductionmentioning

confidence: 99%

Dynamic Covalent Switches and Communicating Networks for Tunable Multicolor Luminescent Systems and Vapor-Responsive Materials

Zou

Yun

et al. 2019

J. Am. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…This growing toolbox includes chemoselective reactions at cysteine residues such as disulfide exchanges, alkylation, native chemical ligation (NCL) with thioester reagents, Michael addition with maleimides or thiol‐ene components following a free‐radical or Michael addition mechanism . In contrast to NCL, thiol‐ene and maleimide coupling strategies, which operate efficiently but yield irreversible bonds, disulfides can be considered as dynamic‐covalent bonds . Upon a redox environment present in an extracellular setting, disulfide bonds are stable, unless subject to disulfide exchange, and are cleaved intracellularly due to the more potent redox environment .…”

Section: Introductionmentioning

confidence: 99%

“…[8,15] In contrast to NCL, [16,17] thiol-ene [18] and maleimide coupling strategies, [19,20] which operate efficiently but yield irreversible bonds, disulfides can be considered asdynamic-covalent bonds. [21][22][23] Upon ar edoxe nvironment present in an extracellular setting, disulfide bonds are stable, unless subject to disulfide exchange, and are cleaved intracellularly due to the more potent redox environment. [24,25] Especially in the development of vaccines, drug, or gene delivery systems, this bioreversibility of disulfides provides enormousb enefits.…”

Section: Introductionmentioning

confidence: 99%

Of Thiols and Disulfides: Methods for Chemoselective Formation of Asymmetric Disulfides in Synthetic Peptides and Polymers

Schäfer

Barz

2018

Chemistry A European J

View full text Add to dashboard Cite

In protein or peptide chemistry, thiols are frequently chosen as a chemical entity for chemoselective modification reactions. Although it is a well-established methodology to address cysteines and homocysteines in aqueous media to form S-C bonds, possibilities for the chemoselective formation of asymmetric disulfides have been less approached. Focusing on bioreversibility in conjugation chemistry, the formation of disulfide bonds is highly desirable for the attachment of thiol-containing bioactive agents to proteins or in cross-linking reactions, because disulfide bonds can combine stability in blood with degradability inside cells. In this Concept article, recent approaches in the field of activating groups for thiol moieties incorporated in peptide and polymer materials are highlighted. Advantageous combinations of stability during synthesis of the material with high reactivity towards thiols are explored focusing on simplification and prevention of side reactions as well as additional deprotection and activation steps prior to disulfide formation. Moreover, applications of this chemistry are highlighted and future perspectives are envisioned.

show abstract

Templated Chromophore Assembly by Dynamic Covalent Bonds

et al. 2015

View full text Add to dashboard Cite

Through the simultaneous use of three orthogonal dynamic covalent reactions,n amely disulfide,b oronate,a nd acyl hydrazone formation, we conceived af acile and versatile protocol to spatially organizet ailored chromophores,w hich absorb in the blue,r ed, and yellow regions,o napreprogrammed a-helix peptide.This approach allowed the assembly of the dyes in the desired ratio and spacing, as dictated by both the relative positioning and distribution of the recognition units on the peptide scaffold. Steady-state UV/Vis absorption and emission studies suggest an energy transfer from the yellowand red donors to the blue acceptor.Am olecular dynamics simulation supports the experimental findings that the helical structure is maintained after the assembly and the three dyes are confined in defined conformational spaces.Natural photosynthesis is initiated by the absorption of sunlight by al arge number of light-harvesting pigments that funnel the excitation energy to areaction center where energy conversion takes place.The efficiencyofthis process relies on aparticular organization and ratio of selected chromophores that enables maximum light absorption and energy conversion.[1]

show abstract

Complex Functional Systems with Three Different Types of Dynamic Covalent Bonds

Cited by 21 publications

References 44 publications

Dynamic Covalent Switches and Communicating Networks for Tunable Multicolor Luminescent Systems and Vapor-Responsive Materials

Dynamic Covalent Switches and Communicating Networks for Tunable Multicolor Luminescent Systems and Vapor-Responsive Materials

Of Thiols and Disulfides: Methods for Chemoselective Formation of Asymmetric Disulfides in Synthetic Peptides and Polymers

Templated Chromophore Assembly by Dynamic Covalent Bonds

Contact Info

Product

Resources

About