A strained alkyne-containing bipyridine reagent; synthesis, reactivity and fluorescence properties

Forshaw, Sam; Knighton, Richard C.; Reber, Jami D; Parker, Jeremy S.; Chmel, Nikola Paul; Wills, Martin

doi:10.1039/c9ra06866j

Cited by 4 publications

References 36 publications

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Multifluorinated Aryl Azides for the Development of Improved H₂S Probes, and Fast Strain‐promoted Azide‐Alkyne Cycloaddition and Staudinger Reactions

Kang

Cai

et al. 2020

Chemistry An Asian Journal

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The development of advanced bioorthogonal reactions for detection and labeling of biomolecules is significant in chemical biology. Recently, researchers have found that multifluorinated aryl azides hold great potential for the development of improved bioorthogonal reactions. The fluorine atom can be a perfect substituent group because of its properties of excellent electronegativity and small steric hindrance. In this Minireview, we discuss recent developments of improved hydrogen sulfide (H 2 S) fluorescence probes, fast strain-promoted azide-alkyne cycloaddition (SPAAC) and nonhydrolysis Staudinger reactions based on the use of multifluorinated aryl azides. Additionally, kinetic studies and biological applications of these reactions are also presented. 2 3 4 5 6 7 8

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Multifluorinated Aryl Azides for the Development of Improved H₂S Probes, and Fast Strain‐promoted Azide‐Alkyne Cycloaddition and Staudinger Reactions

Kang

Cai

et al. 2020

Chemistry An Asian Journal

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Fluorescent probes based on bioorthogonal reactions: Construction strategies and applications

Zhao,

He,

et al. 2023

TrAC Trends in Analytical Chemistry

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4.1 Strain-Promoted Azide–Alkyne Cycloaddition (SPAAC): Background, Substrate Preparation, and Reactivity

Harris¹,

Alabugin²

2022

Click Chemistry

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This chapter discusses the creative synthetic approaches to azides and cycloalkynes, provides the rationale for controlling SPAAC reactivity through tuning cycloalkyne and azide backbone modifications, and highlights research on nitrone cycloadditions with cycloalkynes. This synthetic and knowledge toolset will help in the design of better cycloalkynes and their partners to answer challenging research questions and aid the development of new applications.

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A strained alkyne-containing bipyridine reagent; synthesis, reactivity and fluorescence properties

Abstract: A bipyridyl reagent containing a strained alkyne 7, reacts with benzyl azide to give a significantly more flexible product 10 and an increase in fluorescence is observed. Upon addition of Zn(ii), the fluorescence is enhanced further.

Cited by 4 publications

References 36 publications

Multifluorinated Aryl Azides for the Development of Improved H₂S Probes, and Fast Strain‐promoted Azide‐Alkyne Cycloaddition and Staudinger Reactions

Multifluorinated Aryl Azides for the Development of Improved H₂S Probes, and Fast Strain‐promoted Azide‐Alkyne Cycloaddition and Staudinger Reactions

Fluorescent probes based on bioorthogonal reactions: Construction strategies and applications

4.1 Strain-Promoted Azide–Alkyne Cycloaddition (SPAAC): Background, Substrate Preparation, and Reactivity

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A strained alkyne-containing bipyridine reagent; synthesis, reactivity and fluorescence properties

Abstract: A bipyridyl reagent containing a strained alkyne 7, reacts with benzyl azide to give a significantly more flexible product 10 and an increase in fluorescence is observed. Upon addition of Zn(ii), the fluorescence is enhanced further.

Cited by 4 publications

References 36 publications

Multifluorinated Aryl Azides for the Development of Improved H2S Probes, and Fast Strain‐promoted Azide‐Alkyne Cycloaddition and Staudinger Reactions

Multifluorinated Aryl Azides for the Development of Improved H2S Probes, and Fast Strain‐promoted Azide‐Alkyne Cycloaddition and Staudinger Reactions

Fluorescent probes based on bioorthogonal reactions: Construction strategies and applications

4.1 Strain-Promoted Azide–Alkyne Cycloaddition (SPAAC): Background, Substrate Preparation, and Reactivity

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Product

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About

Multifluorinated Aryl Azides for the Development of Improved H₂S Probes, and Fast Strain‐promoted Azide‐Alkyne Cycloaddition and Staudinger Reactions

Multifluorinated Aryl Azides for the Development of Improved H₂S Probes, and Fast Strain‐promoted Azide‐Alkyne Cycloaddition and Staudinger Reactions