Strain-Promoted Cycloaddition of Cyclopropenes with O-Quinones: A Rapid Click Reaction

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2018 Mar 16

PMID 29542846

Citations 18

Authors

Digvijay Gahtory

Rickdeb Sen

Andriy R Kuzmyn

Jorge Escorihuela

Han Zuilhof

Affiliations

Soon will be listed here.

Abstract

Novel click reactions are of continued interest in fields as diverse as bio-conjugation, polymer science and surface chemistry. Qualification as a proper "click" reaction requires stringent criteria, including fast kinetics and high conversion, to be met. Herein, we report a novel strain-promoted cycloaddition between cyclopropenes and o-quinones in solution and on a surface. We demonstrate the "click character" of the reaction in solution and on surfaces for both monolayer and polymer brush functionalization.

Citing Articles

Click Chemistry for Biofunctional Polymers: From Observing to Steering Cell Behavior.

Ghosal K, Bhattacharyya S, Mishra V, Zuilhof H Chem Rev. 2024; 124(23):13216-13300.

PMID: 39621547 PMC: 11638903. DOI: 10.1021/acs.chemrev.4c00251.

Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents.

Takeda N, Akasaka S, Kawauchi S, Michinobu T Beilstein J Org Chem. 2024; 20:2234-2241.

PMID: 39286793 PMC: 11403804. DOI: 10.3762/bjoc.20.191.

Photo-cycloaddition reactions of vinyldiazo compounds.

Bao M, Luczak K, Chaladaj W, Baird M, Gryko D, Doyle M Nat Commun. 2024; 15(1):4574.

PMID: 38811537 PMC: 11137122. DOI: 10.1038/s41467-024-48274-5.

SI-PET-RAFT in flow: improved control over polymer brush growth.

Kuzmyn A, van Galen M, van Lagen B, Zuilhof H Polym Chem. 2023; 14(29):3357-3363.

PMID: 37497044 PMC: 10367056. DOI: 10.1039/d3py00488k.

Sulfur-Phenolate Exchange: SuFEx-Derived Dynamic Covalent Reactions and Degradation of SuFEx Polymers.

Chao Y, Krishna A, Subramaniam M, Liang D, Pujari S, Sue A Angew Chem Int Ed Engl. 2022; 61(36):e202207456.

PMID: 35819248 PMC: 9540147. DOI: 10.1002/anie.202207456.

References

Tornoe C, Christensen C, Meldal M . Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem. 2002; 67(9):3057-64. DOI: 10.1021/jo011148j. View

Liu F, Liang Y, Houk K . Bioorthogonal Cycloadditions: Computational Analysis with the Distortion/Interaction Model and Predictions of Reactivities. Acc Chem Res. 2017; 50(9):2297-2308. PMC: 5675536. DOI: 10.1021/acs.accounts.7b00265. View

Laughlin S, Baskin J, Amacher S, Bertozzi C . In vivo imaging of membrane-associated glycans in developing zebrafish. Science. 2008; 320(5876):664-7. PMC: 2701225. DOI: 10.1126/science.1155106. View

Castro V, Rodriguez H, Albericio F . CuAAC: An Efficient Click Chemistry Reaction on Solid Phase. ACS Comb Sci. 2015; 18(1):1-14. DOI: 10.1021/acscombsci.5b00087. View

Borrmann A, Fatunsin O, Dommerholt J, Jonker A, Lowik D, van Hest J . Strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) for fast and activatable protein conjugation. Bioconjug Chem. 2014; 26(2):257-61. DOI: 10.1021/bc500534d. View

Bruins J, Westphal A, Albada B, Wagner K, Bartels L, Spits H . Inducible, Site-Specific Protein Labeling by Tyrosine Oxidation-Strain-Promoted (4 + 2) Cycloaddition. Bioconjug Chem. 2017; 28(4):1189-1193. PMC: 5399473. DOI: 10.1021/acs.bioconjchem.7b00046. View

Yang J, Liang Y, Seckute J, Houk K, Devaraj N . Synthesis and reactivity comparisons of 1-methyl-3-substituted cyclopropene mini-tags for tetrazine bioorthogonal reactions. Chemistry. 2014; 20(12):3365-75. PMC: 4020353. DOI: 10.1002/chem.201304225. View

Bruins J, Albada B, van Delft F . ortho-Quinones and Analogues Thereof: Highly Reactive Intermediates for Fast and Selective Biofunctionalization. Chemistry. 2017; 24(19):4749-4756. PMC: 5900998. DOI: 10.1002/chem.201703919. View

Barner-Kowollik C, Du Prez F, Espeel P, Hawker C, Junkers T, Schlaad H . "Clicking" polymers or just efficient linking: what is the difference?. Angew Chem Int Ed Engl. 2010; 50(1):60-2. DOI: 10.1002/anie.201003707. View

10.

Gahtory D, Sen R, Pujari S, Li S, Zheng Q, Moses J . Quantitative and Orthogonal Formation and Reactivity of SuFEx Platforms. Chemistry. 2018; 24(41):10550-10556. PMC: 6099289. DOI: 10.1002/chem.201802356. View

11.

Escorihuela J, Das A, Looijen W, van Delft F, Aquino A, Lischka H . Kinetics of the Strain-Promoted Oxidation-Controlled Cycloalkyne-1,2-quinone Cycloaddition: Experimental and Theoretical Studies. J Org Chem. 2017; 83(1):244-252. PMC: 5759032. DOI: 10.1021/acs.joc.7b02614. View

12.

Kolb H, Finn M, Sharpless K . Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew Chem Int Ed Engl. 2001; 40(11):2004-2021. DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5. View

13.

Kim H, Sachin K, Jeong H, Choi W, Lee H, Kim D . F-18 Labeled RGD Probes Based on Bioorthogonal Strain-Promoted Click Reaction for PET Imaging. ACS Med Chem Lett. 2015; 6(4):402-7. PMC: 4394342. DOI: 10.1021/ml500464f. View

14.

Patterson D, Nazarova L, Xie B, Kamber D, Prescher J . Functionalized cyclopropenes as bioorthogonal chemical reporters. J Am Chem Soc. 2012; 134(45):18638-43. DOI: 10.1021/ja3060436. View

15.

Li S, Wu P, Moses J, Sharpless K . Multidimensional SuFEx Click Chemistry: Sequential Sulfur(VI) Fluoride Exchange Connections of Diverse Modules Launched From An SOF Hub. Angew Chem Int Ed Engl. 2017; 56(11):2903-2908. PMC: 5434761. DOI: 10.1002/anie.201611048. View

16.

Knall A, Slugovc C . Inverse electron demand Diels-Alder (iEDDA)-initiated conjugation: a (high) potential click chemistry scheme. Chem Soc Rev. 2013; 42(12):5131-42. DOI: 10.1039/c3cs60049a. View

17.

Thirumurugan P, Matosiuk D, Jozwiak K . Click chemistry for drug development and diverse chemical-biology applications. Chem Rev. 2013; 113(7):4905-79. DOI: 10.1021/cr200409f. View

18.

Spate A, Busskamp H, Niederwieser A, Schart V, Marx A, Wittmann V . Rapid labeling of metabolically engineered cell-surface glycoconjugates with a carbamate-linked cyclopropene reporter. Bioconjug Chem. 2013; 25(1):147-54. DOI: 10.1021/bc4004487. View

19.

Gao B, Zhang L, Zheng Q, Zhou F, Klivansky L, Lu J . Bifluoride-catalysed sulfur(VI) fluoride exchange reaction for the synthesis of polysulfates and polysulfonates. Nat Chem. 2017; 9(11):1083-1088. PMC: 5972039. DOI: 10.1038/nchem.2796. View

20.

Gahtory D, Sen R, Kuzmyn A, Escorihuela J, Zuilhof H . Strain-Promoted Cycloaddition of Cyclopropenes with o-Quinones: A Rapid Click Reaction. Angew Chem Int Ed Engl. 2018; 57(32):10118-10122. PMC: 6099469. DOI: 10.1002/anie.201800937. View