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TCO(trans-Cyclooctene) Derivatives:The Fastest Click Reaction Reagents

작성자 : 관리자 작성일 : 2024.03.26 17:59




The TCO (trans-cyclooctene) moiety is known for its high internal strain on the double bond, facilitating the Strain-Promoted Inverse Electron-Demand Diels-Alder Reaction (SPIEDAC) with tetrazine derivatives. This reaction proceeds selectively even in the presence of various functional groups, making it applicable as a click chemistry tool. Click chemistry utilizing TCO does not require metal catalysts and exhibits rapid reaction rates as its primary feature. This click chemistry meets the criteria for bioorthogonal reactions (fast, selective, biocompatible, metal-free) and finds applications in a wide range of uses such as protein labeling and imaging.1,2,3,4)



The reaction rate between TCO and tetrazine derivatives is described as [TCO > TCO*] and [axial > equatorial]. However, in biological environments, especially in the presence of thiols, the stability is characterized as [TCO* > TCO].5)


Furthermore, recent reports have indicated that the reaction between 2-TCO derivatives and tetrazine derivatives can exhibit "click-to-release" reactions under metal catalyst-free conditions, showing promise for their role as prodrugs.6,7,8,9)



Based on these characteristics, we offer a variety of TCO derivatives useful for synthesis, including 4-nitrophenyl carbonate (NPC) esters, amines elongated with PEG, biotins, DBCOs, NHS esters, maleimide derivatives, and more.




  Products   

TCO-4-Nitrophenyl Carbonate (NPC) Esters

TCO-NPC equatorial isomerTCO-NPC axial isomerTCO*-NPC axial isomerTCO*-NPC equatorial isomer


* 해당 구조식 클릭 시 제품 상세페이지로 이동됩니다.


  Product   

  T4212   TCO-NPC equatorial isomer

  T4213   TCO-NPC axial isomer

  T4218   TCO*-NPC axial isomer

  T4219   TCO*-NPC equatorial isomer


TCO-PEG-Amines

TCO-PEG3-amine equatorial isomerTCO-PEG3-amine axial isomerTCO*-PEG3-amine equatorial isomer

  Product   

  T4234   TCO-PEG3-amine equatorial isomer

  T4233   TCO-PEG3-amine axial isomer

  T4258   TCO*-PEG3-amine equatorial isomer


TCO-PEG-DBCOs

TCO-PEG3-DBCO axial isomer
TCO-PEG3-DBCO equatorial isomer
TCO*-PEG3-DBCO equatorial isomer


  Product   

  T4238   TCO-PEG3-DBCO axial isomer

  T4239   TCO-PEG3-DBCO equatorial isomer

  T4260   TCO*-PEG3-DBCO equatorial isomer


TCO-PEG-Biotins

TCO-PEG3-Biotin axial isomer
TCO-PEG3-Biotin equatorial isomer
TCO*-PEG3-Biotin equatorial isomer

  Product   

  T4236   TCO-PEG3-Biotin axial isomer

  T4237   TCO-PEG3-Biotin equatorial isomer

  T4259   TCO*-PEG3-Biotin equatorial isomer


TCO-PEG-NHS Esters

TCO-PEG4-NHS
TCO*-PEG3-NHS equatorial isomer

  Product   

  T3949   TCO-PEG4-NHS

  T4262   TCO*-PEG3-NHS equatorial isomer


TCO-PEG-Maleimides

TCO-PEG3-Maleimide
TCO*-PEG3-Maleimide equatorial isomer

  Product   

  T3948   TCO-PEG3-Maleimide

  T4261   TCO*-PEG3-Maleimide equatorial isomer



TCO-Amino Acid

N-(4E)-TCO-L-lysine

  Product   

  T4126   N-(4E)-TCO-L-lysine




* 해당 구조식 클릭 시 제품 상세페이지로 이동됩니다.




  Related Products   

  B6273   b-TzC3744Clofentezine

  D3175   3,6-Diphenyl-1,2,4,5-tetrazine

  D3211   3,6-Di(4-pyridyl)-1,2,4,5-tetrazine

  D3640   3,6-Di(2-pyridyl)-1,2,4,5-tetrazine

  T4125   Tetrazine-NHS Ester

  M3494   Methyltetrazine-NHS Ester

  M3558   [4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl]methanamine Hydrochloride


    References



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