Publication Cover
Catalysis Reviews
Science and Engineering
Volume 62, 2020 - Issue 4
911
Views
9
CrossRef citations to date
0
Altmetric
Research Article

Recent synthesis of functionalized s-tetrazines and their application in ligation reactions under physiological conditions: a concise overview

, , , , , & ORCID Icon show all

References

  • (a) Schreiber, S. L. Small Molecules: The Missing Link in the Central Dogma. Nat. Chem. Bio. 2005, 1, 64. DOI: 10.1038/nchembio0705-64. (b) L. Wang, P. G. Schultz. Angew. Chem. Int. Ed. 2005, 44, 34. (c) P. B. Dervan. Bioorg. Med. Chem. 2005, 9, 2215. (d) J. Clardy, C. Walsh. Nature. 2004, 432, 829. And references cited therein.
  • Hang, H. C.; Yu, C.; Kato, D. L.; Bertozzi, C. R. A Metabolic Labeling Approach toward Proteomic Analysis of Mucin-type O-linked Glycosylation. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 14846. DOI: 10.1073/pnas.2335201100.
  • (a) Lin, F. L.; Hoyt, H. M.; van Halbeek, H.; Bergman, R. G.; Bertozzi, C. R. Mechanistic Investigation of the Staudinger Ligation. J. Am. Chem. Soc. 2005, 127(8), 2686. DOI: 10.1021/ja044461m. (b) H. Staudinger; J. Meyer. Helv. Chim. Acta. 1919, 2, 635. (c) Y. G. Gololobov; I. N. Zhmurova; L. F. Kasukhin. Tetrahedron. 1981, 37, 437. (d) E. F. V. Scriven; K. Turnbull. Chem. Rev. 1988, 88, 297. (e) Y. G. Gololobov; L. F. Kasukhin. Tetrahedron. 1992, 48, 1353. (f) S. Shah; J. D. Protasiewicz. Coord. Chem. Rev. 2000, 210, 181. (g) M. Kohn; R. Breinbauer. Angew. Chem. Int. Ed. 2004, 43, 3106. (h) E. Saxon; C. R. Bertozzi. Science. 2000, 287, 2007. (i) E. Saxon; C. R. Armstrong; C. R. Bertozzi. Org. Lett. 2000, 2, 2141. (j) B. L. Nilsson; L. L. Kiessling; R. T. Raines. Org. Lett. 2000, 2, 1939.
  • (a) Huisgen, R. 1,3-Dipolar Cycloadditions. Past and Future. Angew. Chem. Int. Ed. Engl. 1963, 2, 565. DOI: 10.1002/(ISSN)1521-3773. (b) P. Wu; V. V. Fokin. Aldrichimica Acta. 2007, 40, 7.
  • (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chem. Int. Ed. 2001, 40, 2004. DOI: 10.1002/(ISSN)1521-3773. (b) V. V. Rostovtsev; L. G. Green; V. V. Fokin; K. B. Sharpless. Angew. Chem., Int. Ed. 2002, 41, 2596. (c) W. G. Lewis; L. G. Green; F. Grynszpan; Z. Radić; P. R. Carlier; P. Taylor; M. G. Finn; K. B. Sharpless. Angew. Chem. Int. Ed. 2002, 41, 1053. (d) T. R. Chan; R. Hilgraf; K. B. Sharpless; V. V. Fokin. Org. Lett. 2004, 6, 2853. (e) A. Krasiński; Z. Radić; R. Manetsch; J. Raushel; P. Taylor; K. B. Sharpless; H. C. Kolb. J. Am. Chem. Soc. 2005, 127(18), 6686.
  • (a) Saxon, E.; Bertozzi, C. R. Cell Surface Engineering by a Modified Staudinger Reaction. Sci.. 2000, 287, 2007. DOI: 10.1126/science.287.5460.2007. (b) J. A. Prescher and C. R. Bertozzi. Nat. Chem. Biol. 2005, 1, 13. (c) E. M. Sletten and C. R. Bertozzi. Angew. Chem. Int. Ed. 2009, 48, 6974. (d) E. M. Sletten and C. R. Bertozzi. Acc. Chem. Res. 2011, 44, 666.
  • (a) Blackman, M. L.; Royzen, M.; Fox, J. M. Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity. J. Am. Chem. Soc. 2008, 130, 13518. DOI: 10.1021/ja8053805. (b) M. T. Taylor; M. L. Blackman; O. Dmitrenko and J. M. Fox. J. Am. Chem. Soc. 2011, 133, 9646. (c) M. Royzen; G. P. A. Yap; J. M. Fox. J. Am. Chem. Soc. 2008, 130, 3760.
  • (a) McKay, C. S.; Finn, M. G. Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation. Chem. Biol. 2014, 21, 1075. DOI: 10.1016/j.chembiol.2014.09.002. (b) S. I. Presolski; D. D. Diaz; V. V. Fokin; M. G. Finn. J. Am. Chem. Soc. 2007, 129, 12705.
  • (a) Lim, R. K. V.; Lin, Q. Bioorthogonal Chemistry: Recent Progress and Future Directions. Chem. Commun. 2010, 46, 1589. DOI: 10.1039/b925931g. (b) C. P. Ramil and Q. Lin. Chem. Commun. 2013, 49, 11007. (c) Z.-P. Zhou; Q. Lin. J. Am. Chem. Soc. 2014, 136, 4153. And references cited therein.
  • (a) Patterson, D. M.; Nazarova, L. A.; Prescher, J. A. Finding the Right (Bioorthogonal) Chemistry. ACS Chem. Biol. 2014, 9, 592. DOI: 10.1021/cb400828a. (b) H.-W. Shih; D. N. Kamber and J. A. Prescher. Curr. Opin. Chem. Biol. 2014, 21, 103. (c) D. M. Patterson and J. A. Prescher. Curr. Opin. Chem. Biol. 2015, 28, 141.
  • (a) Devaraj, N. K.; Weissleder, R. Biomedical Applications of Tetrazine Cycloadditions. Acc. Chem. Res. 2011, 44, 816. DOI: 10.1021/ar200037t. (b) J. Šečkutė and N. K. Devaraj. Curr. Opin. Chem. Biol. 2013, 17, 761. (c) H. Wu and N. K. Devaraj. Top. Curr. Chem. 2016, 374, 1. (d) N. K. Devaraj; R. Weissleder and S. A. Hilderbrand. Bioconjugate Chem. 2008, 19, 2297. And references cited therein.
  • (a) Li, J.; Chen, P. R. Development and Application of Bond Cleavage Reactions in Bioorthogonal Chemistry. Nat. Chem. Biol. 2016, 12, 129. DOI: 10.1038/nchembio.2024. (b) J. Li; S. Jia; P. Chen. Nat. Chem. Biol. 2014, 10, 1003. (c) J. Li; J. Yu; J. Zhao; J. Wang; S. Zheng; S. Lin; L. Chen; M. Yang; S. Jia; X. Zhang and P. R. Chen. Nat. Chem. 2014, 6, 352.
  • (a) Lang, K.; Chin, J. W. Bioorthogonal Reactions for Labeling Proteins. ACS Chem. Biol. 2014, 9, 16. DOI: 10.1021/cb4009292. (b) M. King and A. Wagner. Bioconjugate Chem. 2014, 25, 825. (c) O. Boutureira and G. J. L. Bernardes. Chem. Rev. 2015, 115, 2174. (d) K. A. Mix; M. R. Aronoff; R. T. Raines. ACS Chem. Bio. 2016, 11(12), 3233. (e) C. W. Tornoe; C. Christensen; M. Meldal. J. Org. Chem. 2002, 67, 3057. (e) A. C. Knall and C. Slugovc. Chem. Soc. Rev. 2013, 42, 5131. (f) B. L. Oliveira; Z. Guo and G. J. L. Bernardes. Chem. Soc. Rev. 2017, 46, 4895. (g) W. Chen; D. Wang; C. Dai; D. Hamelberg and B. Wang. Chem. Commun. 2012, 48, 1736. (h) J.-B. Li; H. Kong; L. Huang; B. Cheng; K. Qin; M.-M. Zheng; Z. Yan and Y. Zhang. J. Am. Chem. Soc. 2016, 138, 15943.
  • (a) Schulz, D.; Rentmeister, A. Current Approaches for RNA Labeling in Vitro and in Cells Based on Click Reactions. Chembiochem. 2014, 15, 2342. DOI: 10.1002/cbic.201402240. (b) S. Kath-Schorr. Top. Curr. Chem. 2016, 374, 4. (c) K. Gutsmiedl; C. T. Wirges; V. Ehmke and T. Carell. Org. Lett. 2009, 11, 2405. (d). J. Schoch; S. Ameta and A. Jaschke. Chem. Commun. 2011, 47, 12536. (e) A. M. Pyka; C. Domnick; F. Braun and S. Kath-Schorr. Bioconjugate Chem. 2014, 25, 1438. (f) P. N. Asare-Okai; E. Agustin; D. Fabris and M. Royzen. Chem. Commun. 2014, 50, 7844. (g) J. M. Holstein; L. Anhauser and A. Rentmeister. Angew. Chem., Int. Ed. 2016, 55, 10899. (H) M. L. Winz; E. C. Linder; T. Andre; J. Becker and A. Jaschke. Nucleic Acids Res. 2015, 43, e110. And references cited therein.
  • (a) Liu, -C.-C.; Schultz, P. G. Adding New Chemistries to the Genetic Code. Annu. Rev. Biochem. 2010, 79, 413. DOI: 10.1146/annurev.biochem.052308.105824. (b) J. Xie and P. G. Schultz. Nat. Rev. Mol. Cell Biol. 2006, 7, 775. (c) L. Davis and J. W. Chin. Nat. Rev. Mol. Cell Biol. 2012, 13, 168. (d) A. Gautier; D. P. Nguyen; H. Lusic; W. An; A. Deiters and J. W. Chin. J. Am. Chem. Soc. 2010, 132, 4086. And references cited therein. Especially, the work has been extensively disclosed by Schultz, Wang, Chin, Deiters and Chen etc.
  • (a) Varki, A. Biological roles of glycans, Glycobiology. 2017, 27, 3. (b) K. Ohtsubo and J. D. Marth. Cell. 2006, 126, 855. (c) T. J. Sminia; H. Zuilhof and T. Wennekes. Carbohydr. Res. 2016, 435, 121. (d) A. A. Neves; H. Stöckmann; Y. A. Wainman; J. C. H. Kuo; S. Fawcett; F. J. Leeper and K. M. Brindle. Bioconjugate Chem. 2013, 24, 934. (e) P. Agarwal; B. J. Beahm; P. Shieh and C. R. Bertozzi. Angew. Chem., Int. Ed. 2015, 54, 11504.
  • (a) Hang, H. C.; Wilson, J. P.; Charron, G. Bioorthogonal Chemical Reporters for Analyzing Protein Lipidation and Lipid Trafficking. Acc. Chem. Res. 2011, 44, 699. DOI: 10.1021/ar200063v. (b) R. S. Erdmann; H. Takakura; A. D. Thompson; F. Rivera-Molina; E. S. Allgeyer; J. Bewersdorf; D. Toomre and A. Schepartz. Angew. Chem., Int. Ed. 2014, 53, 10242.
  • Li, Z.; Wang, D.; Li, L.; Pan, S.; Na, Z.; Tan, C. Y.; Yao, S. Q. “Minimalist” Cyclopropene-Containing Photo-Cross-Linkers Suitable for Live-Cell Imaging and Affinity-Based Protein Labeling. J. Am. Chem. Soc. 2014, 136, 9990. DOI: 10.1021/ja502780z.
  • (a) Zeng, D.; Zeglis, B. M.; Lewis, J. S.; Anderson, C. J. The Growing Impact of Bioorthogonal Click Chemistry on the Development of Radiopharmaceuticals. J. Nucl. Med. 2013, 54, 829. DOI: 10.2967/jnumed.112.115550. (b) J. Y. Choi and B. C. Lee. Nucl. Med. Mol. Imaging. 2015, 49, 258. (c) J. Marik and J. L. Sutcliffe. Tetrahedron Lett. 2006, 47, 6681. (d) H. S. Gill and J. Marik. Nat. Protoc. 2011, 6, 1718. (e) S. Maschauer and O. Prante. Carbohydr. Res. 2009, 344, 753. (f) B. H. Rotstein; N. A. Stephenson; N. Vasdev and S. H. Liang. Nat. Commun. 2014, 5, 4365. (g) L. Mirfeizi; J. Walsh; H. Kolb; L. Campbell-Verduyn; R. A. Dierckx; B. L. Feringa; P. H. Elsinga; T. de Groot; I. Sannen; G. Bormans and S. Celen. Nucl. Med. Biol. 2013, 40, 710. (h) T. L. Mindt; H. Struthers; L. Brans; T. Anguelov; C. Schweinsberg; V. Maes; D. Tourwé and R. Schibli. J. Am. Chem. Soc. 2006, 128, 15096.
  • (a) Wang, K.; Sachdeva, A.; Cox, D. J.; Wilf, N. M.; Lang, K.; Wallace, S.; Mehl, R. A.; Chin, J. W. Optimized Orthogonal Translation of Unnatural Amino Acids Enables Spontaneous Protein Double-labelling and FRET. Nat. Chem. 2014, 6, 393. DOI: 10.1038/nchem.1919. (b) T. Peng and H. C. Hang. J. Am. Chem. Soc. 2016, 138, 14423. (c) C. Uttamapinant; J. D. Howe; K. Lang; V. Beranek; L. Davis; M. Mahesh; N. P. Barry and J. W. Chin. J. Am. Chem. Soc. 2015, 137, 4602. (d) J. Seckute; J. Yang and N. K. Devaraj. Nucleic Acids Res. 2013, 41, e148. (e) T. S. Elliott; F. M. Townsley; A. Bianco; R. J. Ernst; A. Sachdeva; S. J. Elsasser; L. Davis; K. Lang; R. Pisa; S. Greiss; K. S. Lilley and J. W. Chin. Nat. Biotechnol. 2014, 32, 465. (f) D. L. Alge; M. A. Azagarsamy; D. F. Donohue and K. S. Anseth. Biomacromolecules. 2013, 14, 949. (g) S. Hong; J. Carlson; H. Lee and R. Weissleder. Adv. Healthcare Mater. 2016, 5, 421. (h) V. X. Truong; M. P. Ablett; S. M. Richardson; J. A. Hoyland and A. P. Dove. J. Am. Chem. Soc. 2015, 137, 1618. (i) K. Kawamoto; S. C. Grindy; J. Liu; N. Holten-Andersen and J. A. Johnson. ACS Macro Lett. 2015, 4, 458. (j) H. Zhang; K. T. Dicker; X. Xu; X. Jia and J. M. Fox. ACS Macro Lett. 2014, 3, 727.
  • Carboni, R. A.; Lindsay, R. V. Reactions of Tetrazines with Unsaturated Compounds. A New Synthesis of Pyridazines. J. Am. Chem. Soc. 1959, 81, 4342. DOI: 10.1021/ja01525a060.
  • (a) Sauer, J. Eine Studie der Diels-Alder-Reaktion, III: Umsetzungen von 1.2.4.5-Tetrazinen mit Olefinen. Zur Struktur von Dihydropyridazinen. Chem. Ber. 1965, 98, 1435. DOI: 10.1002/(ISSN)1099-0682. (b) J. Sauer; G. Heinrichs. Tetrahedron Lett. 1966, 4979 and references cited therein. (c) D. R. Soenen; J. M. Zimpleman; D. L. Boger. J. Org. Chem. 2003, 68, 3593. (d) J. S. Oakdale; D. L. Boger. Org. Lett. 2010, 12, 1132. (e) K. Lee; Y. B. Poudel; C. M. Glinkerman; D. L. Boger. Tetrahedron. 2015, 71, 5897.
  • (a) Clavier, G.; Audebert, P. s-Tetrazines as Building Blocks for New Functional Molecules and Molecular Materials. Chem. Rev. 2010, 110(6), 3299. DOI: 10.1021/cr900357e. (b) N. K. Devaraj; R. Weissleder. Acc. Chem. Res. 2011, 44(9), 816. (c) Y. Kim; J. Do; E. Kim; G. Clavier; L. Galmiche; P. Audebert. J. Electroanal. Chem. 2009, 632(1–2), 201. (d) C. Quinton; V. Alain-Rizzo; C. Dumas-Verdes; G. Clavier; F. Miomandre; P. Audebert. Eur. J. Or.g Chem. 2012, 7, 1394. (f) C. Garau; D. Quinonero; A. Frontera; A. Costa; P. Ballester; P. M. Deya. Chem. Phys. Lett. 2003, 370(1–2), 7. (g) P. Hrdlovic; J. Donovalova; H. Stankovicova; A. Gaplovsky. Molecules. 2010, 15(12), 8915. (h) L. N. Bogdanova; N. O. Mchedlov-Petrossyan; N. A. Vodolazkaya; A. V. Lebed. Carbohyd. Res. 2010, 345(13), 1882. (i) N. Saracoglu. Tetrahedron. 2007, 63, 4199. (j) Qing Zhou. Synthesis of new tetrazines functionalized with photoactive and electroactive groups. Other. École normale supérieure de Cachan-ENS Cachan, 2012. English. NNT: 2012DENS0039.
  • Pioneering works: (a) Audebert, P. First Example of an Electroactive Polymer Issued from an Oligothiophene Substituted Tetrazine. Electrochem. Commun. 2004, 6, 144. DOI: 10.1016/j.elecom.2003.11.001. (b) P. Audebert; F. Miomandre; G. Clavier; M. C. Vernieres; S. Badre and R. Meallet-Renaud. Chem.-Eur. J. 2005, 11, 5667. (c) Y.-H. Gong; F. Miomandre; R. Meallet-Renault; S. Badre; L. Galmiche; J. Tang; P. Audebert and G. Clavier. Eur. J. Org. Chem. 2009, 6121. (d) D. E. Chavez; D. A. Parrish. J. Heterocyclic Chem. 2009, 46, 88. (e) D. E. Chavez; S. K. Hanson; J. M. Veauthier; D. A. Parrish. Angew. Chem. Int. Ed. 2013, 52, 6876. (f) D. E. Chavez; T. W. Myers; J. M. Veauthier; M. T. Greenfield; R. J. Scharff; D. A. Parrish. Synlett. 2013, 26, 2029. (g) D. E. Chavez; D. A. Parrish; L. Mitchell. Angew. Chem. Int. Ed. 2016, 55, 8666. (h) W. Kaim. Coord. Chem. Rev. 2002, 230, 127. (i) N. K. Deravaj. Synlett. 2012, 23, 2147. (j) N. K. Devaraj; R. Weissleder. Acc. Chem. Res. 2011, 44, 816. (k) A. M. Churakov; V. A. Tartakovsky. Chem. Rev. 2004, 104, 2601.
  • Pinner, A. Ueber die Einwirkung von Hydrazin auf Imidoäther. Ber. Dtsch. Chem. Ges. 1893, 26, 2126. DOI: 10.1002/(ISSN)1099-0682.
  • (a) Abdelrah, M.; Kira, M. A.; Tolba, M. N. A Direct Synthesis of Dihydrotetrazines. Tetrahedron Lett. 1968, 35, 3871. DOI: 10.1016/S0040-4039(01)99123-3. (b) D.-Z. Wang; W.-X. Chen; Y.-Q. Zheng; C.-F. Dai; K. Wang; B.-W. Ke and B.-H. Wang. Org. Biomol. Chem. 2014, 12, 3950. (c) D. Wang; W. Chen; Y. Zheng; C. Dai; L. Wang and B. Wang. Heterocycl. Commun. 2013, 19, 171. (d) D.-S. Liu; A. Tangpeerachaikul; R. Selvaraj; M. T. Taylor; J. M. Fox and A. -Y. Ting. J. Am. Chem. Soc. 2012, 134, 792.
  • (a) Larsen, C.; Binderup, E.; Moller, J. Mass Spectrometry of 1,2,4,5-Tetrazines. Acta. Chem. Scand. 1967, 21, 2855. DOI: 10.3891/acta.chem.scand.21-2855. (b) W. Skorianetz; E. S. Kovats. Hel. Chim. Acta. 1971, 54, 1922. (c) W. Skorianetz; E. S. Kovats. Hel. Chim. Acta. 1972, 55, 1404.
  • Junghahn, A. Neue Methode zur Darstellung von Tetrazinderivaten. Berichte der Deutschen Chemischen Gesellschaft. 1898, 31, 312. DOI: 10.1002/(ISSN)1099-0682.
  • (a) Lang, K.; Davis, L.; Torres-Kolbus, J.; Chou, C.; Deiters, A.; Chin, J. W. Genetically Encoded Norbornene Directs Site-specific Cellular Protein Labelling via a Rapid Bioorthogonal Reaction. Nat. Chem. 2012, 4, 298. DOI: 10.1038/nchem.1250. (b) J. Ding; Z. Li; Z. Cui; G. P. Robertson; N. Song; X. Du; L. J. Scoles. Poly. Sci. Part A (Polym. Sci.) 2011, 49, 3374. (c) G.-W. Rao; W.-X. Hu. Bioorg. Med. Chem. Lett. 2006, 16, 3702. (d) W. Kaim; Zeitschrift fuer Fees; J. B. Naturforschung. Chem. Sci. 1995, 50, 123. (e) M. L. Blackman; M. Royzen; J. M. Fox. J. Am. Chem. Soc. 2008, 130, 13518. (f) J. Sauer; G. R. Pabst; U. Holland; H.-S. Kim; S. Loebbecke. Eur. J. Org. Chem. 2001, 697. (g) M. D. Coburn; G. A. Buntain; B. W. Harris; M. A. Hiskey; K. Y. Lee; D. G. Ott. J. Heterocycl. Chem. 1991, 28, 2049. (h) C. M. Asselin; G. C. Fraser; H. K. Jr. Hall; W. E. Lindsell; A. B. Padias; P. N. Preston. J. Chem. Soc., Dalton Trans. 1997, 20, 3765.
  • Selvaraj, R.; Fox, J. M. An Efficient and Mild Oxidant for the Synthesis of S-tetrazines. Tetrahedron Lett. 2014, 55, 4795. DOI: 10.1016/j.tetlet.2014.07.012.
  • Yang, J.; Karver, M. R.; Li, W.; Sagu, S.; Devaraj, N. K. Metal-Catalyzed One-Pot Synthesis of Tetrazines Directly from Aliphatic Nitriles and Hydrazine. Angew. Chem. Int. Ed. 2012, 51, 5222. DOI: 10.1002/anie.201201117.
  • Mao, W.-Y.; Shi, W.; Li, J.; Su, D.-Y.; Wang, X.-M.; Zhang, L.-Y.; Pan, -L.-L.; Wu, X.-A.; Wu, H.-X. Organocatalytic and Scalable Syntheses of Unsymmetrical 1,2,4,5-Tetrazines by Thiol-Containing Promotors. Angew. Chem. Int. Ed. 2019, 58, 1106. DOI: 10.1002/anie.201812550.
  • (a) Qu, FranÅois-Xavier Sauvage, -Y.-Y.; Audebert, P.; Audebert, P.; Audebert, P. Metal-Free Synthetic Approach to 3-Monosubstituted Unsymmetrical 1,2,4,5-Tetrazines Useful for Bioorthogonal Reactions. Angew. Chem. Int. Ed. 2018, 57, 12057. DOI: 10.1002/anie.201804878. (b) C. Li; H.-X. Ge; B. Yin; M.-Y. She; P. Liu; X.-D. Lia and J.-L. Li. RSC Adv. 2015, 5, 12277.
  • (a) Wieczorek, A.; Werther, P.; Euchner, J.; Wombacher, R. Green- to Far-red-emitting Fluorogenic Tetrazine Probes – Synthetic Access and No-wash Protein Imaging inside Living Cells. Chem. Sci. 2017, 8, 1506. DOI: 10.1039/C6SC03879D. (b) Q. Zhou; P. Audebert; G. Clavier; F. Miomandre; J. Tang. RCS Adv. 2014, 4, 7193. (c) C. Quinton; V. Alain-Rizzo; C. Dumas-Verdes; G. Clavier; L. Vignau; P. Audebert. New J. Chem. 2015, 39, 9700. (d) A. Wieczorek; T. Buckup; R. Wombacher. Org. Biomol. Chem. 2014, 12, 4177.
  • Novák, Z.; Kotschy, A. First Cross-Coupling Reactions on Tetrazines. Org. Lett. 2003, 5, 3495. DOI: 10.1021/ol035312w.
  • Leconte, N.; Keromnes-Wuillaume, A.; Suzenet, F.; Guillaumet, G. Efficient Palladium-Catalyzed Synthesis of Unsymmetrical (Het)aryl-tetrazines. Synlett. 2007, 2007, 0204. DOI: 10.1055/s-2007-967991.
  • Bender, A. M.; Chopko, T. C.; Bridges, T. M.; Lindsley, C. W. Preparation of Unsymmetrical 1,2,4,5-Tetrazines via a Mild Suzuki Cross-Coupling Reaction. Org. Lett. 2017, 19, 5693. DOI: 10.1021/acs.orglett.7b02868.
  • Wu, H.; Yang, J.; Šečkutė, J.; Devaraj, N. K. In Situ Synthesis of Alkenyl Tetrazines for Highly Fluorogenic Bioorthogonal Live-Cell Imaging Probes. Angew. Chem. Int. Ed. 2014, 53, 5805. DOI: 10.1002/anie.201400135.
  • Lambert, W. D.; Fang, Y.-Z.; Mahapatra, S.; Huang, Z.; Am Ende, C. W.; Fox, J. M. Installation of Minimal Tetrazines through Silver-Mediated Liebeskind–Srogl Coupling with Arylboronic Acids. J. Am. Chem. Soc. 2019, 141, 17068–17074. DOI: 10.1021/jacs.9b08677.
  • (a) Coburn, M. D.; Buntain, G. A.; Harris, B. W.; Hiskey, M. A.; Lee, K. Y.; Ott, D. G. An Improved Synthesis of 3,6-diamino-1,2,4,5-tetrazine. II. From Triaminoguanidine and 2,4-pentanedione. J. Heterocyclic Chem. 1991, 28, 2049. DOI: 10.1002/jhet.v28:8. (b) F. Bentiss; M. Lagrenée; M. Traisnel; B. Mernari; H. Elattari. J. Heterocyclic Chem. 1999, 36, 149. (c) M. D. Coburn; M. A. Hiskey; K. Y. Lee; D. G. Ott; M. M. Stinecipher. J. Heterocyclic Chem. 1993, 30, 1593. (d) D. E. Chavez; M. A. Hiskey. J. Heterocyclic Chem. 1998, 35, 1329. (e) M. D. Helm; A. Plant; J. P. A. Harrity. Org. Biomol. Chem. 2006, 4, 4278.
  • (a) Boger, D. L.; Schaum, R. P.; Garbaccio, R. M. Regioselective Inverse Electron Demand Diels−Alder Reactions of N-Acyl 6-Amino-3-(methylthio)-1,2,4,5-tetrazines. J. Org. Chem. 1998, 63, 6329. DOI: 10.1021/jo980795g. (b) D. L. Boger, S. M. Sakya, J. Org Chem., 1988, 53, 1415; (c) S. C. Benson, L. Lee, L. Yang, J. K. Snyder, Tetrahedron, 2000, 56, 1165; (d) S. M. Sakya, K. K. Groskopf, D. L. Boger, Tetrahedron Lett., 1997, 38, 3805; (e) F. Neugebauer, Melliand Textil. Int., 1982, 63, 384; (f) P. Audebert, S. Sadki, F. Miomandre, G. Clavier, M. C. Vernieres, M. Saoud, P. Hapiot, New J. Chem., 2004, 28, 387; (g) N. I. Latosh, G. L. Rusinov, I. N. Ganebnykh, O. N. Chupakhin, Zh Org Khim+, 1999, 35, 1392; (h) C. Glidewell, P. Lightfoot, B. J. L. Royles, D. M. Smith, J. Chem. Soc.-Perkin Transactions 2, 1997, 6, 1167; (i) H. Yamanaka, S. Ohba, Heterocycles, 1990, 31, 895; (j) A. Counottepotman, H. C. Vanderplas, B. Vanveldhuizen, J. Org. Chem., 1981, 46, 2138; (k) Z. Novak, B. Bostai, M. Csekei, K. Lorincz, A. Kotschy, Heterocycles, 2003, 60, 2653; (l) Y. H. Gong, P. Audebert, J. Tang, F. Miomandre, G. Clavier, S. Badre, R. Meallet-Renault, J. Marrot, J. Electroanal. Chem., 2006, 592, 147; (m) Z. Qing, P. Audebert, G. Clavier, F. Miomandre, J. Tang, T. T. Vu, R. Meallet-Renault, J. Electroanal. Chem., 2009, 632, 39.
  • Sheremetev, A. B.; Palysaeva, N. V.; Struchkova, M. I.; Suponitsky, K. Y. A Mild and Efficient Synthesis of 3-Hetarylamino-s-Tetrazines. Medeleev Comm. 2012, 22, 302. DOI: 10.1016/j.mencom.2012.11.007.
  • (a) Stollé, R. 60. Über die Überführung von Hydrazinabkömmlingen in heterocyklische Verbindungen. J. Prakt. Chem. 1906, 73, 277. DOI: 10.1002/prac.19060730118. (b) D.-Z. Wang, W.-X. Chen, Y.-Q. Zheng, C.-F. Dai, L.-F. Wang, B.-H. Wang, Heterocycl. Commun., 2013, 19, 171.
  • Farago, J.; Novak, Z.; Schlosser, G.; Csampai, A.; Kotschy, A. The Azaphilic Addition of Organometallic Reagents on Tetrazines: Scope and Limitations. Tetrahedron. 2004, 60, 1991. DOI: 10.1016/j.tet.2004.01.013.
  • (a) Boger, D. L.; Panek, J. S. 1,2,4-triazine Preparation via Thermal Cycloaddition of Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with Aryl Thioimidates. Tetrahedron Lett. 1983, 24, 4511. DOI: 10.1016/S0040-4039(00)85941-9. (b) D. L. Boger, Chem. Rev., 1986, 86, 781.
  • Representative and references cited therein (a) Blackman, M. L.; Royzen, M.; Fox, J. M. Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels−Alder Reactivity. J. Am. Chem. Soc. 2008, 130, 13518. DOI: 10.1021/ja8053805. (b) E. M. Sletten and C. R. Bertozzi, Angew. Chem. Int. Ed., 2009, 48, 6974; (c) C. R. Bertozzi, Acc. Chem. Res., 2011, 44, 651; (d) B. L. Oliveira, Z. Guo and G. J. L. Bernardes, Chem. Soc. Rev., 2017, 46, 4895; (e) N. K. Devaraj, ACS Cent. Sci., 2018, 4, 952; (f) B. J. Levandowski, R. F. Gamache, J. M. Murphy, and K. N. Houk, J. Am. Chem. Soc., 2018, 140, 6426; (g) J. Li and P. Chen, Nat. Chem. Bio., 2016, 12, 129.
  • (a) Rossin, R.; van Duijnhoven, S. M. J.; Ten Hoeve, W.; Janssen, H. M.; Kleijn, L. H. J.; Hoeben, F. J. M.; Versteegen, R. M.; Robillard, M. S. Triggered Drug Release from an Antibody–Drug Conjugate Using Fast “Click-to-release” Chemistry in Mice. Bioconjugate Chem. 2016, 27, 1697. DOI: 10.1021/acs.bioconjchem.6b00231. (b) J. M. O. Mejia, I. Khan, L. Seebald, M. Royzen, ACS Cent. Sci., 2016, 2, 476; (c) M. Czuban, S. Srinivasan, N. A. Yee, E. Agustin, A. Koliszak, E. Miller, I. Khan, I. Qunones, H. Noory, C. Motola, R. Volkmer, M. Di Luka, A. Trampuz, M. Royzen, J. M. Mejia Oneto, ACS Cent. Sci., 2018, 4, 1624.
  • (a) Sauer, J.; Heldmann, D. K.; Hetzenegger, J.; Krauthan, J.; Sichert, H.; Schuster, J. 1,2,4,5-Tetrazine: Synthesis and Reactivity in [4+2] Cycloadditions. Eur. J. Org. Chem. 1998, 12, 2885. DOI: 10.1002/(ISSN)1099-0690. (b) F. Thalhammer, U. Wallfahrer, J. Sauer, Tetrahedron Lett., 1990, 31, 6851; (c) D. R. Soenen, J. M. Zimpleman, D. L. Boger, J. Org. Chem., 2003, 68, 3593; (d) D. L. Boger, R. S. Coleman, J. S. Panek, F. X. Huber, J. Sauer, J. Org. Chem., 1985, 50, 5377; (e) D. L. Boger, R. P. Schaum, R. M. Garbaccio, J. Org. Chem., 1998, 63, 6329.
  • (a) Royzen, M.; Yap, G. P. A.; Fox, J. M. A Photochemical Synthesis of Functionalized trans-Cyclooctenes Driven by Metal Complexation. J. Am. Chem. Soc. 2008, 130, 3760. DOI: 10.1021/ja8001919. (b) M. R. Karver, R. Weissleder, S. A. Hilderbrand, Bioconjugate Chem., 2011, 22, 2263; (c) I. A. Barker, D. J. Hall, C. F. Hansell, F. E. Du Prez, R. K. O’Reilly, A. P. Dove, Macromol. Rapid Comm., 2011, 32, 1362.
  • (a) Ehret, F.; Wu, H.; Alexander, S. C.; Devaraj, N. K. Electrochemical Control of Rapid Bioorthogonal Tetrazine Ligations for Selective Functionalization of Microelectrodes. J. Am. Chem. Soc. 2015, 137, 8876. DOI: 10.1021/jacs.5b03371. (b) X.-Y. Fan, Y. Ge, F. Lin, Y. Yang, G. Zhang, W. S. C. Ngai, Z. Lin, S.-Q. Zheng, J. Wang, J.-Y. Zhao, J. Li, P. R. Chen, Angew. Chem. Int. Ed., 2016, 55, 14046; (c) J. Li, S. Jia, P.-R. Chen, Nat. Chem. Bio., 2014, 10, 1003; (d) G. Zhang, J. Li, R. Xie, X. Fan, Y. Liu, S. Zheng, Y. Ge, P. R. Chen, ACS Cent. Sci., 2016, 2, 325; (e) Z. Li, H. Cai, M. Hassink, M. L. Blackman, R. C. D. Brown, P. S. Conti, J. M. Fox, Chem. Commun., 2010, 46, 8043; (f) M. T. Taylor, M. L. Blackman, O. Dmitrenko, and J. M. Fox, J. Am. Chem. Soc., 2011, 133, 9646; (g) J. L. Seitchik, J. C. Peeler, M. T. Taylor, M. L. Blackman, T. W. Rhoads, R. B. Cooley, C. Refakis, J. M. Fox, R. A. Mehl, J. Am. Chem. Soc., 2012, 134, 2898; (h) K. Lang, L. Davis, S. Wallace, M. Mahesh, D. J. Cox, M. L. Blackman, J. M. Fox, J. W. Chin, J. Am. Chem. Soc., 2012, 134, 10317; (i) S. Liu, M. Hassink, R. Selvaraj, L.-P. Yap, R. Park, H. Wang, X. Chen, J. Fox, Z. Li, P. S. Conti, Molecular Imaging, 2013, 12, 121; (j) Z. Wu, S. Liu, M. Hassink, I. Nair, R. Park, L. Li, I. Todorov, J. M. Fox, Z. Li, J. E. Shively, P. S. Conti, F. Kandeel, J. Nuclear Med., 2013, 54, 244; (k) H. Zhang, K. T. Dicker, X. Xu, X. Jia, J. M. Fox, ACS Macro Lett., 2014, 3, 727; (l) R. Selvaraj, B. Giglio, S. Liu, H. Wang, M. Wang, H. Yuan, S. R. Chintala, L.-P. Yap, P. S. Conti, J. M. Fox, Z. Li, Bioconjugate Chem., 2015, 26, 435; (m) S. Liu, H. Zhang, R. A. Remy, F. Deng, M. E. Mackay, J. M. Fox, X. Jia, Adv. Mater, 2015, 27, 2783; (n) H. E. Murrey, J. C. Judkins, C. W. am Ende, T. E. Ballard, Y. Fang, K. Riccardi, L. Di, E. R. Guilmette, J. W. Schwartz, J. M. Fox, D. S. Johnson, J. Am. Chem. Soc., 2015, 137, 11461; (o) M. Wang, D. Svatunek, K. Rohlfing, Y. Liu, H. Wang, B. Giglio, H. Yuan, Z. Wu, Z. Li, J. M. Fox, Theranostics 2016, 6, 887; (p) K. T. Dicker, J. Song, A. Moore, H. Zhang, Y. Li, D. L. Burris, X. Jia, J. M. Fox, Chem. Sci., 2018, 9, 5394; (q) R. J. Blizzard, D. R. Backus, W. Brown, C. G. Bazewicz, Y. Li, R. A. Mehl, J. Am. Chem. Soc., 2015, 137, 10044; (r) I. Nikic, T. Plass, O. Schraidt, J. Szymanski, J. A. Briggs, C. Schultz, E. A. Lemke, Angew. Chem. Int. Ed., 2014, 53, 2245; (s) A. Darko, S. Wallace, O. Dmitrenko, M. M. Machovina, R. A. Mehl, J. W. Chin, J. M. Fox, Chem. Sci., 2014, 5, 3770; (t) F. Muttach, N. Muthmann, D. Reichert, L. Anhäuser and A. Rentmeister, Chem. Sci., 2017, 8, 7947; (u) Y.-Y. Wu, J.-L. Hu, C. Sun, Y. Cao, Y.-Y. Li, F.-Y. Xie, T.-Y. Zeng, B. Zhou, J.-J. Du and Y.-F. Tang, Bioconjugate Chem., 2018, 29, 2287.
  • (a) Patterson, D. M.; Nazarova, L. A.; Xie, B.; Kamber, D. N.; Prescher, J. A. Functionalized Cyclopropenes As Bioorthogonal Chemical Reporters. J. Am. Chem. Soc. 2012, 134, 18638. DOI: 10.1021/ja3060436. (b) D. N. Kamber, L. A. Nazarova, Y. Liang, S. A. Lopez, D. M. Patterson, H.- W. Shih, K. N. Houk, and J. A. Prescher, J. Am. Chem. Soc., 2013, 135, 13680; (c) J. Yang, J. Seckute, C. M. Cole, N. K. Devaraj, Angew. Chem. Int. Ed., 2012, 51, 7476; (d) J. Yang, Y. Liang, J. ŠeČkutè, K. N. Houk, and N. K. Devaraj, Chem. Eur. J., 2014, 20, 3365; (e) B. Oller-Salvia, G. Kym, J. W. Chin. Angew. Chem.Int. Ed., 2018, 57, 2831.
  • (a) Ramil, C. P.; Dong, M.-Q.; An, P.; Lewandowski, T. M.; Yu, Z.-P.; Miller, L. J.; Lin, Q. Spirohexene-Tetrazine Ligation Enables Bioorthogonal Labeling of Class B G Protein-Coupled Receptors in Live Cells. J. Am. Chem. Soc. 2017, 139, 13376. DOI: 10.1021/jacs.7b05674. (b) Z. Yu, Q. Lin, J. Am. Chem. Soc., 2014, 136, 4153.
  • (a) Engelsma, S. B.; Willems, L. I.; van Paaschen, C. E.; van Kasteren, S. I.; van der Marel, G. A.; Overkleeft, H. S.; Filippov, D. V. Acylazetine as a Dienophile in Bioorthogonal Inverse Electron-Demand Diels–Alder Ligation. Org. Lett. 2014, 16, 2744. DOI: 10.1021/ol501049c. (b) U. Rieder and N. W. Luedtke, Angew. Chem. Int. Ed., 2014, 53, 9168; (c) A. Niederwieser, Anne-Katrin Späte, L. D. Nguyen, C. Jüngst, W. Reutter, and V. Wittmann, Angew. Chem. Int. Ed., 2013, 52, 4265; (d) S. Eising, F. Lelivelt, and K. M. Bonger, Angew. Chem. Int. Ed., 2016, 55, 12243; (e) B. L. Oliveira, Z.-J. Guo, O. Boutureira, A. Guerreiro, G. Jiménez‐Osés, G. J. L. Bernardes, Angew. Chem. Int. Ed., 2016, 55, 14683; (f) H.-X. Wu, S. C. Alexander, S.-J. Jin, and N. K. Devaraj, J. Am. Chem. Soc., 2016, 138, 11429; (g) J.-B. Li, H. Kong, L. Huang, B. Cheng, K. Qin, M.-M. Zheng, Z. Yan and Y. Zhang, J. Am. Chem. Soc., 2018, 140, 14542.
  • (a) Tu, J.-L.; Xu, M.-H.; Parvez, S.; Peterson, R. T.; Franzini, R. M. Bioorthogonal Removal of 3-Isocyanopropyl Groups Enables the Controlled Release of Fluorophores and Drugs in Vivo. J. Am. Chem. Soc. 2018, 140, 16793. DOI: 10.1021/jacs.8b05093. (b) Y. A. Wainman, A. A. Neves, S. Stairs, H. Stöckmann, H. Ireland-Zecchini, K. M. Brindle, F. J. Leeper, Org. Biomol. Chem., 2013, 11, 7297; (c) H. Stöckmann, A. A. Neves, S. Stairs, K. M. Brindle, F. J. Leeper, Org. Biomol. Chem., 2011, 9, 7303; (d) S. Stairs, A. A. Neves, H. Stöckmann, Y. A. Wainman, H. Ireland-Zecchini, K. M. Brindle, F. J. Leeper, ChemBioChem., 2013, 14, 1063; (e) A. A. Neves, H. Stöckmann, Y. A. Wainman, J. C. Kuo, S. Fawcett, F. J. Leeper, K. M. Brindle, Bioconjugate Chem., 2013, 24, 934.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.