cycloaddition reaction


Summary: Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products.

Top Publications

  1. Aioub A, Dahora L, Gamble K, Finn M. Selection of Natural Peptide Ligands for Copper-Catalyzed Azide-Alkyne Cycloaddition Catalysis. Bioconjug Chem. 2017;28:1693-1701 pubmed publisher
  2. Jana S, Iram S, Thomas J, Liekens S, Dehaen W. Synthesis and anticancer activity of novel aza-artemisinin derivatives. Bioorg Med Chem. 2017;25:3671-3676 pubmed publisher
    ..92 and 1.2µM, respectively. ..
  3. Sang X, Chen S, Tang M, Wang H, An X, Lu X, et al. ?-Pyrone derivatives with cytotoxic activities, from the endophytic fungus Phoma sp. YN02-P-3. Bioorg Med Chem Lett. 2017;27:3723-3725 pubmed publisher
    ..The structure-activity relationships of these phomones were also reported. ..
  4. Dasari R, La Clair J, Kornienko A. Irreversible Protein Labeling by Paal-Knorr Conjugation. Chembiochem. 2017;18:1792-1796 pubmed publisher
    ..Although these are fundamental tools, there is a need for the discovery of reactions that can label native proteins. We report herein the adaptation of the Paal-Knorr reaction to label lysine residues in proteins via pyrrole linkages. ..
  5. Yang Z, Abdellaoui H, He W, Xu J. Ortho-Nitro Effect on the Diastereoselective Control in Sulfa-Staudinger and Staudinger Cycloadditions. Molecules. 2017;22: pubmed publisher
    ..The current research provides further insights into the diastereoselective control in sulfa-Staudinger and Staudinger cycloadditions. ..
  6. Sipthorp J, Lebraud H, Gilley R, Kidger A, Okkenhaug H, Saba El Leil M, et al. Visualization of Endogenous ERK1/2 in Cells with a Bioorthogonal Covalent Probe. Bioconjug Chem. 2017;28:1677-1683 pubmed publisher
  7. Jeon B, Wang S, Ruszczycky M, Liu H. Natural [4 + 2]-Cyclases. Chem Rev. 2017;117:5367-5388 pubmed publisher
    ..While mechanistic investigation of these enzymes is just beginning, recent studies have provided new insights with implications for understanding their biosynthetic roles, mechanisms of catalysis, and evolutionary origin. ..
  8. Lin B, Zhou G, Gong Y, Wei Q, Tian M, Liu X, et al. Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3'-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction. Molecules. 2017;22: pubmed publisher
  9. Lu T, Lu Z, Ma Z, Zhang Y, Hsung R. Allenamides: a powerful and versatile building block in organic synthesis. Chem Rev. 2013;113:4862-904 pubmed publisher

More Information


  1. Jiang X, Wang R. Recent developments in catalytic asymmetric inverse-electron-demand Diels-Alder reaction. Chem Rev. 2013;113:5515-46 pubmed publisher
  2. Prier C, Rankic D, MacMillan D. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem Rev. 2013;113:5322-63 pubmed publisher
  3. Hamadani K, Howe J, Jensen M, Wu P, Cate J, Marqusee S. An in vitro tag-and-modify protein sample generation method for single-molecule fluorescence resonance energy transfer. J Biol Chem. 2017;292:15636-15648 pubmed publisher
  4. Sherratt A, Rouleau Y, Luebbert C, Strmiskova M, Veres T, Bidawid S, et al. Rapid Screening and Identification of Living Pathogenic Organisms via Optimized Bioorthogonal Non-canonical Amino Acid Tagging. Cell Chem Biol. 2017;24:1048-1055.e3 pubmed publisher
    ..The methods reported allow for the very rapid screening and identification of living pathogenic organisms. ..
  5. Longin O, van de Langemheen H, Liskamp R. An orthogonally protected CycloTriVeratrylene (CTV) as a highly pre-organized molecular scaffold for subsequent ligation of different cyclic peptides towards protein mimics. Bioorg Med Chem. 2017;25:5008-5015 pubmed publisher
    ..This approach may find wide applications for development of protein-protein interaction disruptors as well as synthetic vaccines. ..
  6. Song M, Cao C, He Q, Dong Q, Li D, Tang J, et al. Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions. Bioorg Med Chem. 2017;25:5290-5302 pubmed publisher
    ..In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin. ..
  7. Yakushiji F, Muguruma K, Hayashi Y, Shirasaka T, Kawamata R, Tanaka H, et al. Click strategy using disodium salts of amino acids improves the water solubility of plinabulin and KPU-300. Bioorg Med Chem. 2017;25:3623-3630 pubmed publisher
    ..With this flexibility, we are approaching to the in vivo study using water-soluble derivative. ..
  8. Kalaoglu Altan O, Kirac Aydin A, Sümer Bolu B, Sanyal R, Sanyal A. Diels-Alder "Clickable" Biodegradable Nanofibers: Benign Tailoring of Scaffolds for Biomolecular Immobilization and Cell Growth. Bioconjug Chem. 2017;28:2420-2428 pubmed publisher
  9. Zhong W, Bobbink F, Fei Z, Dyson P. Polyimidazolium Salts: Robust Catalysts for the Cycloaddition of Carbon Dioxide into Carbonates in Solvent-Free Conditions. ChemSusChem. 2017;10:2728-2735 pubmed publisher
    ..The polymer catalysts exhibit long-term stability and may be recycled and reused at least 10?times. ..
  10. Kitamura Y, Asakura R, Terazawa K, Shibata A, Ikeda M, Kitade Y. Nucleobase azide-ethynylribose click chemistry contributes to stabilizing oligonucleotide duplexes and stem-loop structures. Bioorg Med Chem Lett. 2017;27:2655-2658 pubmed publisher
  11. Ylijoki K, Stryker J. [5 + 2] cycloaddition reactions in organic and natural product synthesis. Chem Rev. 2013;113:2244-66 pubmed publisher
  12. Ghannay S, Bakari S, Ghabi A, Kadri A, Msaddek M, Aouadi K. Stereoselective synthesis of enantiopure N-substituted pyrrolidin-2,5-dione derivatives by 1,3-dipolar cycloaddition and assessment of their in vitro antioxidant and antibacterial activities. Bioorg Med Chem Lett. 2017;27:2302-2307 pubmed publisher
    ..Finally, the preliminary results obtained from this investigation attempted to clarify if the structurally different side chains of active compounds interfere with their biological properties. ..
  13. Singh A, Viljoen A, Kremer L, Kumar V. Azide-alkyne cycloaddition en route to 4-aminoquinoline-ferrocenylchalcone conjugates: synthesis and anti-TB evaluation. Future Med Chem. 2017;9:1701-1708 pubmed publisher
    ..of a series of 4-aminoquinoline-ferrocenylchalcone conjugates via Cu-promoted Huisgen's azide-alkyne cycloaddition reaction and evaluation of their antitubercular activities against mc26230 strain of Mycobacterium ..
  14. Mali P, Shirsat P, Khomane N, Nayak L, Nanubolu J, Meshram H. 1,3-Dipolar Cycloaddition Reactions for the Synthesis of Novel Oxindole Derivatives and Their Cytotoxic Properties. ACS Comb Sci. 2017;19:633-639 pubmed publisher
    ..Most of the compounds showed moderate to potent cytotoxic activity against the tested cell lines. ..
  15. Yamamura H. Chemical Modification of Cyclodextrin and Amylose by Click Reaction and Its Application to the Synthesis of Poly-alkylamine-Modified Antibacterial Sugars. Chem Pharm Bull (Tokyo). 2017;65:312-317 pubmed publisher
    ..This review will describe the results of our microwave-assisted click reaction for the poly-modification of CD and amylose molecules, and its application to the study of synthetic membrane active antibacterial derivatives. ..
  16. Pan T, Xia C, Jiang H, Zhang Z, Zhu X, Yang Y. Chemical Synthesis of the ODM-201's Diastereomers through an Efficient Intramolecular 1,3-Dipolar Cycloaddition. Chem Pharm Bull (Tokyo). 2017;65:582-585 pubmed publisher
  17. Bjerknes M, Cheng H, McNitt C, Popik V. Facile Quenching and Spatial Patterning of Cylooctynes via Strain-Promoted Alkyne-Azide Cycloaddition of Inorganic Azides. Bioconjug Chem. 2017;28:1560-1565 pubmed publisher
    ..The facile quenching of cyclooctynes demonstrated here should be useful in other bioorthogonal ligation techniques in which cyclooctynes are employed, including SPANC, Diels-Alder, and thiol-yne...
  18. Xu Z, Song X, Hu Y, Qiang M, Lv Z. Azide-alkyne cycloaddition towards 1H-1,2,3-triazole-tethered gatifloxacin and isatin conjugates: Design, synthesis and in vitro anti-mycobacterial evaluation. Eur J Med Chem. 2017;138:66-71 pubmed publisher
    ..0->128 ?g/mL) against MDR-TB. Unfortunately, both of the two hybrids (CC50: 7.8 ?g/mL) were much more cytotoxic than the other derivatives, need to be further optimized. ..
  19. Raddaoui N, Stazzoni S, Möckl L, Viverge B, Geiger F, Engelke H, et al. Dendrimer-Based Signal Amplification of Click-Labelled DNA in Situ. Chembiochem. 2017;18:1716-1720 pubmed publisher
  20. Swiderska K, Szlachcic A, Czyrek A, Zakrzewska M, Otlewski J. Site-specific conjugation of fibroblast growth factor 2 (FGF2) based on incorporation of alkyne-reactive unnatural amino acid. Bioorg Med Chem. 2017;25:3685-3693 pubmed publisher
    ..The detergent-based optimization approach may help overcome problems with the CuAAC reaction yield for protein modification with hydrophobic compounds, such as MMAE. ..
  21. Liu X, Qin Y. Enabling syntheses of diterpenoid alkaloids and related diterpenes by an oxidative dearomatization/Diels-Alder cycloaddition strategy. Nat Prod Rep. 2017;34:1044-1050 pubmed publisher
    ..This powerful strategy has recently been utilized in the syntheses of diverse diterpenoid alkaloids and their biogenetically relevant diterpenes, which is the subject of this Highlight. ..
  22. Dovgan I, Ursuegui S, Erb S, Michel C, Kolodych S, Cianférani S, et al. Acyl Fluorides: Fast, Efficient, and Versatile Lysine-Based Protein Conjugation via Plug-and-Play Strategy. Bioconjug Chem. 2017;28:1452-1457 pubmed publisher
    ..This translates into better control of the DoC and enables the efficient and fast functionalization of delicate biomolecules at low temperature...
  23. Wu N, Ma W, Mao S, Wu Y, Jin H. Total Synthesis of Tanshinone I. J Nat Prod. 2017;80:1697-1700 pubmed publisher
  24. Farzan V, Ulashchik E, Martynenko Makaev Y, Kvach M, Aparin I, Brylev V, et al. Automated Solid-Phase Click Synthesis of Oligonucleotide Conjugates: From Small Molecules to Diverse N-Acetylgalactosamine Clusters. Bioconjug Chem. 2017;28:2599-2607 pubmed publisher
    ..The approach is suitable for high-throughput synthesis of oligonucleotide conjugates ranging from fluorescent DNA probes to various multi-GalNAc derivatives of 2'-modified siRNA...
  25. Alim N, Miyazaki S, Shimoda Y, Sugiura M, Nakajima M, Kotani S. Asymmetric Aldol/Vinylogous Aldol/Cyclization Reaction Using Phosphine Oxide Catalysts. Chem Pharm Bull (Tokyo). 2017;65:989-993 pubmed publisher
  26. Chen S, Li Q, Liu X, Wu J, Zhang S, Wang H. Polycyclization Enabled by Relay Catalysis: One-Pot Manganese-Catalyzed C-H Allylation and Silver-Catalyzed Povarov Reaction. ChemSusChem. 2017;10:2360-2364 pubmed publisher
    ..process is described for the one-pot synthesis of polycyclic products by a formal [3+2] and [4+2] cycloaddition reaction cascade...
  27. Thapa B, Munk B, Burrows C, Schlegel H. Computational Study of Oxidation of Guanine by Singlet Oxygen (1 Δg ) and Formation of Guanine:Lysine Cross-Links. Chemistry. 2017;23:5804-5813 pubmed publisher
    ..These results are in good agreement with the experimental results for the formation of guanine-lysine cross-links by oxidation by type II photosensitizers. ..