scholarly journals Highly Norbornylated Cellulose and Its “Click” Modification by an Inverse-Electron Demand Diels–Alder (iEDDA) Reaction

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1358
Author(s):  
Christina Wappl ◽  
Viktor Schallert ◽  
Christian Slugovc ◽  
Astrid-Caroline Knall ◽  
Stefan Spirk
Keyword(s):  
Reaction Kinetics ◽  
Acid Chloride ◽  
Click Reaction ◽  
Diels Alder ◽  
Dipolar Cycloaddition ◽  
Direct Reaction ◽  
Cellulosic Material ◽  
Inverse Electron Demand ◽  
High Degree ◽  
Electron Demand

A facile, catalyst-free synthesis of a norbornylated cellulosic material (NC) with a high degree of substitution (2.9) is presented by direct reaction of trimethylsilyl cellulose with norbornene acid chloride. The resulting NC is highly soluble in organic solvents and its reactive double bonds were exploited for the copper-free inverse-electron demand Diels–Alder (iEDDA) “click” reaction with 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine. Reaction kinetics are comparable to the well-known Huisgen type 1,3-dipolar cycloaddition of azide with alkynes, while avoiding toxic catalysts.

scholarly journals Bio-orthogonal “click-and-release” donation of caged carbonyl sulfide (COS) and hydrogen sulfide (H2S)

2017 ◽  
Vol 53 (8) ◽  
pp. 1378-1380 ◽  
Author(s):  
Andrea K. Steiger ◽  
Yang Yang ◽  
Maksim Royzen ◽  
Michael D. Pluth
Keyword(s):  
Hydrogen Sulfide ◽  
Click Reaction ◽  
Carbonyl Sulfide ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
New Strategy ◽  
Electron Demand

The inverse-electron demand Diels–Alder (IEDDA) click reaction between thiocarbamate-functionalized trans-cyclooctenes and tetrazines provides a new strategy for bio-orthogonal COS/H2S delivery.

Monochromophoric iridium(iii) pyridyl–tetrazine complexes as a unique design strategy for bioorthogonal probes with luminogenic behavior

2017 ◽  
Vol 53 (23) ◽  
pp. 3299-3302 ◽  
Author(s):  
Tommy Siu-Ming Tang ◽  
Hua-Wei Liu ◽  
Kenneth Kam-Wing Lo
Keyword(s):  
Reaction Kinetics ◽  
Design Strategy ◽  
Alder Reaction ◽  
Diels Alder ◽  
Metal Coordination ◽  
Coordination Property ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

This is the first reported use of the metal-coordination property of tetrazine in the construction of luminogenic bioorthogonal probes and modulation of the inverse electron-demand Diels–Alder reaction kinetics.

Fast-forming BMSC-encapsulating hydrogels through bioorthogonal reaction for osteogenic differentiation

2018 ◽  
Vol 6 (10) ◽  
pp. 2578-2581 ◽  
Author(s):  
Yajie Zhang ◽  
Hong Chen ◽  
Tingting Zhang ◽  
Yue Zan ◽  
Tianyu Ni ◽  
...  
Keyword(s):  
Hyaluronic Acid ◽  
Osteogenic Differentiation ◽  
Click Reaction ◽  
Diels Alder ◽  
Bioorthogonal Reaction ◽  
Inverse Electron Demand ◽  
Electron Demand

An injectable in situ fast-forming hydrogel was fabricated to encapsulate BMSCs for osteogenic differentiation through the inverse electron demand Diels–Alder click reaction between trans-cyclooctene-modified PEG and tetrazine-modified hyaluronic acid.

ChemInform Abstract: The Diels-Alder-Reaction with Inverse-Electron-Demand - A Review of an Efficient & Attractive Click-Reaction Concept

ChemInform ◽  
2014 ◽  
Vol 45 (41) ◽  
pp. no-no
Author(s):  
Manfred Wiessler ◽  
Waldemar Waldeck ◽  
Ruediger Pipkorn ◽  
Peter Lorenz ◽  
Juergen Debus ◽  
...  
Keyword(s):  
Click Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
Electron Demand

Highly Electron-Deficient Pyridinium-Nitrones for Rapid and Tunable Inverse-Electron-Demand Strain-Promoted Alkyne-Nitrone Cycloaddition to Bicyclo[6.1.0]nonyne

2019 ◽  
Author(s):  
Praveen Gunawardene ◽  
Wilson Luo ◽  
Alexander M. Polgar ◽  
John F. Corrigan ◽  
Mark Workentin
Keyword(s):  
Density Functional Theory ◽  
Reaction Kinetics ◽  
Density Functional ◽  
Functional Theory ◽  
X Ray ◽  
Inverse Electron Demand ◽  
X Ray Crystallography ◽  
Electron Demand

<div> <div> <p>Highly accelerated inverse-electron-demand strain-promoted alkyne-nitrone cycloaddition (IED SPANC) between a sta- ble cyclooctyne (bicyclo[6.1.0]nonyne (BCN)) and nitrones delocalized into a Cα-pyridinium functionality is reported, with the most electron-deficient “pyridinium-nitrone” displaying among the most rapid cycloadditions to BCN that is currently reported. Density functional theory (DFT) and X-ray crystallography are explored to rationalize the effects of N- and Cα-substituent modifications at the nitrone on IED SPANC reaction kinetics and the overall rapid reactivity of pyridinium-delocalized nitrones.</p> </div> </div>

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

2019 ◽  
Author(s):  
Zijian Guo ◽  
Bruno Oliveira ◽  
Claudio D. Navo ◽  
Pedro M. S. D. Cal ◽  
Francisco Corzana ◽  
...  
Keyword(s):  
Protein Modification ◽  
Cross Reactivity ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
On Demand ◽  
Strained Alkenes ◽  
Electron Demand

<p>Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (<i>t</i><sub>1/2</sub>≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.</p>

Potassium Arylethynyltrifluoroborate as an Unstrained Dienophile for Ultrafast and On Demand Activation of Bioorthogonal IEDDA Reactions

2019 ◽  
Author(s):  
Zijian Guo ◽  
Bruno Oliveira ◽  
Claudio D. Navo ◽  
Pedro M. S. D. Cal ◽  
Francisco Corzana ◽  
...  
Keyword(s):  
Protein Modification ◽  
Cross Reactivity ◽  
Diels Alder ◽  
Inverse Electron Demand ◽  
On Demand ◽  
Strained Alkenes ◽  
Electron Demand

<p>Strained alkenes and alkynes are the predominant dienophiles used in inverse electron-demand Diels-Alder (IEDDA) reactions, however, their instability, cross-reactivity and accessibility are problematic. Unstrained dienophiles, although physiologically stable and synthetically accessible, react with tetrazines significantly slower relative to strained variants. Here we report the development of potassium arylethynyltrifluoroborates as unstrained dienophiles for ultrafast, chemically triggered IEDDA reactions. By varying the substituents on the tetrazine (e.g. pyridyl- to benzyl-substituents), cycloaddition rates can vary from nearly spontaneous (<i>t</i><sub>1/2</sub>≈ 9 s) to no reaction with the unstrained alkyne-BF3 dienophile. The reported system was applied to protein modification and enabled mutually orthogonal labelling of two distinct proteins.</p>

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