Method Of Synthesizing Tetrazines
Researchers at the University of California have discovered that Lewis acid metal catalysts, most notably divalent nickel and zinc salts, can catalyze the one-pot synthesis of 1,2,4,5-tetrazines directly from commercially available starting materials. The reaction is a single step process with a high yield. This methodology should greatly improve the accessibility of tetrazines, allowing the synthesis of compounds previously unobtainable in useful quantities, and lead to further exploration of their applications.
Inventor: DEVARAJ, Neal, K. | YANG, Jun | SECKUTE, Jolita
Priority Number: WO2013152359A1
IPC Current: C07D023726 | C07D025708 | C07H000902
Assignee Applicant: The Regents of the University of California
Title: NOVEL TETRAZINES AND METHOD OF SYNTHESIZING THE SAME | NOUVELLES TÉTRAZINES ET LEUR PROCÉDÉ DE SYNTHÈSE
Usefulness: NOVEL TETRAZINES AND METHOD OF SYNTHESIZING THE SAME | NOUVELLES TÉTRAZINES ET LEUR PROCÉDÉ DE SYNTHÈSE
Summary: For synthesizing diazonorcaradiene compound; for synthesizing 3,6-disubstituted 1,2,4,5-tetrazine compound; for synthesizing compound comprising cyclopropene-amino hexanose; for detecting presence of compound in cell; and for ligating first nucleic acid and second nucleic acid (all claimed) such as for detecting single nucleotide polymorphism (SNP) discrimination.
Novelty: New substituted diazonorcaradiene useful compounds for detecting presence of compound in cell, and for ligating first nucleic acid and second nucleic acid such as for detecting single nucleotide polymorphism discrimination
化工/材料
化工/材料应用
9533957
State Of Development A direct demonstration of the process has been published using a variety of reactants and catalysts. Additional studies with the technique show how bioorthogonal conjugations may be performed in labeling reactions to synthesize cyclopropene tags useful for live-cell imaging. More recently, studies have examined applications for agricultural chemistry with the synthesis of cyclopropenes capable of delaying the ripening of fruits, vegetables, and ornamental flowers. More details are available at; J. Yang, M. R. Karver, W. Li, S. Sagu, N. K. Devaraj "Metal-Catalyzed One-Pot Synthesis of Tetrazines Directly from Aliphatic Nitriles and Hydrazine" Angew. Chem. Int. Ed., 2012, 51(21), 5222-5225. A demonstration of using the technique to make cyclopropene tags is available at; J. Yang, J. Šečkutė, C. M. Cole, N. K. Devaraj "Live-Cell Imaging of Cyclopropene Tags with Fluorogenic Tetrazine Cycloadditions" Angew. Chem. Int. Ed., 2012, 51(30), 7476-7479 Other Information http://devarajgroup.ucsd.edu/index.html Intellectual Property Info U.S. rights available. A published patent application detailing this technology is available (hyperlink below under Patent Status). Related Materials Šeckute J., Devaraj N.K. “Expanding room for tetrazine ligations in the in vivo chemistry toolbox” Curr Opin Chem Biol. 2013 Oct;17(5):761-7. doi: 10.1016/j.cbpa.2013.08.004 Tech ID/UC Case 22813/2012-252-0 Related Cases 2012-252-0
Šeckute J., Yang J., Devaraj N.K. “Rapid oligonucleotide-templated fluorogenic tetrazine ligations” Nucleic Acids Res. 2013 Aug;41(15):e148. doi: 10.1093/nar/gkt540
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