TCO-NHS ester

Names

[ CAS No. ]:
1191901-33-3

[ Name ]:
TCO-NHS ester

[Synonym ]:
1-({[(4Z)-4-Cycloocten-1-yloxy]carbonyl}oxy)-2,5-pyrrolidinedione
2,5-Pyrrolidinedione, 1-[[[(4Z)-4-cycloocten-1-yloxy]carbonyl]oxy]-

Biological Activity

[Description]:

TCO-NHS ester is an alkyl/ether-based PROTAC linker that can be used in the synthesis of PROTACs[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> PROTAC >> PROTAC Linker

[Target]

Alkyl/ether

[In Vitro]

PROTACs contain two different ligands connected by a linker; one is a ligand for an E3 ubiquitin ligase and the other is for the target protein. PROTACs exploit the intracellular ubiquitin-proteasome system to selectively degrade target proteins[1].

[References]

[1]. An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
369.1±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₃H₁₇NO₅

[ Molecular Weight ]:
267.278

[ Flash Point ]:
177.0±28.7 °C

[ Exact Mass ]:
267.110687

[ LogP ]:
1.45

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.540

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Articles

Synthesis and evaluation of a series of 1,2,4,5-tetrazines for bioorthogonal conjugation.

Bioconjug. Chem. 22 , 2263-2270, (2011)

1,2,4,5-Tetrazines have been established as effective dienes for inverse electron demand [4 + 2] Diels-Alder cycloaddition reactions with strained alkenes for over 50 years. Recently, this reaction pa...

Tetrazine-based cycloadditions: application to pretargeted live cell imaging.

Bioconjug. Chem. 19 , 2297-2299, (2008)

Bioorthogonal tetrazine cycloadditions have been applied to live cell labeling. Tetrazines react irreversibly with the strained dienophile norbornene forming dihydropyrazine products and dinitrogen. T...

Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity.

J. Am. Chem. Soc. 130 , 13518-13519, (2008)

Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tol...