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Literature DB >> 25005038

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne.

Lucie Plougastel¹, Oleksandr Koniev, Simon Specklin, Elodie Decuypere, Christophe Créminon, David-Alexandre Buisson, Alain Wagner, Sergii Kolodych, Frédéric Taran.

Abstract

New sydnone derivatives have been synthesized and screened for their capacity to undergo fast copper-free cycloaddition reaction with bicyclo-[6.1.0]-nonyne. The influences of substitution in positions N-3 and C-4 of sydnones have been particularly studied leading to the identification of highly reactive partners for bio-orthogonal ligation reactions.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2014 PMID： 25005038 DOI： 10.1039/c4cc03816a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

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Cited

10 in total

Review 1. Click chemistry in complex mixtures: bioorthogonal bioconjugation.

Authors: Craig S McKay; M G Finn
Journal: Chem Biol Date: 2014-09-18

2. Developing bioorthogonal probes to span a spectrum of reactivities.

Authors: Sean S Nguyen; Jennifer A Prescher
Journal: Nat Rev Chem Date: 2020-07-21 Impact factor: 34.035

3. Synthesis of [¹⁸ F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones.

Authors: Maruthi Kumar Narayanam; Gaoyuan Ma; Pier Alexandre Champagne; Kendall N Houk; Jennifer M Murphy
Journal: Angew Chem Int Ed Engl Date: 2017-09-07 Impact factor: 15.336

4. Origins of halogen effects in bioorthogonal sydnone cycloadditions.

Authors: Huimin Tao; Fang Liu; Ruxin Zeng; Zhuzhou Shao; Lufeng Zou; Yang Cao; Jennifer M Murphy; K N Houk; Yong Liang
Journal: Chem Commun (Camb) Date: 2018-05-15 Impact factor: 6.222

5. Superfast Tetrazole-BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells.

Authors: Gangam Srikanth Kumar; Stefano Racioppi; Eva Zurek; Qing Lin
Journal: J Am Chem Soc Date: 2021-12-29 Impact factor: 15.419

6. Clickable Albumin Nanoparticles for Pretargeted Drug Delivery toward PD-L1 Overexpressing Tumors in Combination Immunotherapy.

Authors: Christoph Gerke; Irene Zabala Gutierrez; Diego Méndez-González; M Carmen Iglesias-de la Cruz; Francisca Mulero; Daniel Jaque; Jorge Rubio-Retama
Journal: Bioconjug Chem Date: 2022-04-28 Impact factor: 6.069

Review 7. Light-Triggered Click Chemistry.

Authors: Gangam Srikanth Kumar; Qing Lin
Journal: Chem Rev Date: 2020-10-26 Impact factor: 72.087

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne.

Review 1. Click chemistry in complex mixtures: bioorthogonal bioconjugation.

2. Developing bioorthogonal probes to span a spectrum of reactivities.

3. Synthesis of [¹⁸ F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones.

4. Origins of halogen effects in bioorthogonal sydnone cycloadditions.

5. Superfast Tetrazole-BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells.

6. Clickable Albumin Nanoparticles for Pretargeted Drug Delivery toward PD-L1 Overexpressing Tumors in Combination Immunotherapy.

Review 7. Light-Triggered Click Chemistry.

Review 8. Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides.

Review 9. [3 + 2]-Cycloaddition reaction of sydnones with alkynes.

10. Fast and Efficient Postsynthetic DNA Labeling in Cells by Means of Strain-Promoted Sydnone-Alkyne Cycloadditions.

4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne.

Review 1. Click chemistry in complex mixtures: bioorthogonal bioconjugation.

2. Developing bioorthogonal probes to span a spectrum of reactivities.

3. Synthesis of [18 F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones.

4. Origins of halogen effects in bioorthogonal sydnone cycloadditions.

5. Superfast Tetrazole-BCN Cycloaddition Reaction for Bioorthogonal Protein Labeling on Live Cells.

6. Clickable Albumin Nanoparticles for Pretargeted Drug Delivery toward PD-L1 Overexpressing Tumors in Combination Immunotherapy.

Review 7. Light-Triggered Click Chemistry.

Review 8. Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides.

Review 9. [3 + 2]-Cycloaddition reaction of sydnones with alkynes.

10. Fast and Efficient Postsynthetic DNA Labeling in Cells by Means of Strain-Promoted Sydnone-Alkyne Cycloadditions.

3. Synthesis of [¹⁸ F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones.