Data sheet TCO-NHS ester - Jena Bioscience

Data sheet
TCO-NHS ester
Trans-Cyclooctene-NHS ester
TCO-Carbonate; (E)-Cyclooct-4-enyl-2,5-dioxo-1-pyrrolidinyl carbonate
Cat. No.
CLK-1016-25
CLK-1016-100
CLK-1016-1G
Amount
25 mg
100 mg
1 g
Applications
Protein-protein conjugates
Protein-antibody conjugates
O
Protein-small molecule conjugates
O
O
N
18F radiolabelling
Protein-oligonucleotide conjugates
O
O
Surface modification
Molecular Formula: C 13 H 17 NO 5
Molecular Weight: 267.28 g/mol
CAS number: 1191901-33-3
Purity: > 95 % (functionalization with DBCO-amine
followed by HPLC)
Appearance: solid
Solubility: Chloroform, DCM, DMF, DMSO
Storage conditions: store at -20 °C
Shelf life: 12 months
For research use only!
Description
The inverse-electron demand Diels-Alder cycloaddition reaction
of Trans-Cyclooctenes (TCO) with tetrazines is a
bioorthogonal reaction that possesses exceptional kinetics
(k > 800 M -1 s -1 ) and selectivity. Such excellent reaction
rate constants are unparalleled by any other bioorthogonal
reaction pair described to date.
The extremely fast kinetics and selectivity enables the
conjugation of two low abundance biopolymers in an
aqueous and otherwise complex chemical environment
through the formation of a stable dihydropyridazine. This
bioorthogonal reaction possesses extreme selectivity and
biocompatibility, such that the complimentary reagents
can form covalent bonds within richly functionalized
biological systems, in some cases, living organisms. The
TCO-tetrazine click reaction is a very powerful tool in
catalyst-free protein-protein bioconjugation.
Advanced Features
• By far, the fastest kinetics among any other
bioorthogonal reaction pairs
• Reactions complete in 30-60 minutes at low protein
concentrations (5-10 µM)
• TCO functional group remains stable in aqueous
buffered media (weeks at 4°C, pH 7.5)
• Conjugation efficiency > 99 % without requiring a
toxic catalyst (e.g. Cu(I))
Jena Bioscience GmbH | Löbstedter Str. 80 | 07749 Jena, Germany | Tel.:+49-3641-6285 000 | Fax:+49-3641-6285 100
http://www.jenabioscience.com
Last update: Jun 14, 2013

Data sheet
TCO-NHS ester
Trans-Cyclooctene-NHS ester
TCO-Carbonate; (E)-Cyclooct-4-enyl-2,5-dioxo-1-pyrrolidinyl carbonate
Important Product Information
• TCO-NHS ester is not soluble in aqueous buffers.
• Not recommended for labeling biopolymers in aqueous
media due to very poor labeling efficiency.
Selected References:
Karver et al. (2012) Bioorthogonal Reaction Pairs Enable Simultaneous,
Selective, Multi-Target Imaging. Angew. Chem. Int. Ed. 51:920.
Devaraj et al. (2009) Fast and Sensitive Pre-Targeted Labeling of
Cancer Cells through a Tetrazine/trans-Cyclooctene Cycloaddition.
Angew. Chem. Int. Ed. 48:7013.
Haun et al. (2009) Probing Intracellular Biomarkers and Mediators of
Cell Activation Using Nanosensor and Bioorthogonal Chemistry. ACS
Nano. 5:3204.
Blackman et al. (2008) Tetrazine Ligation: Fast Bioconjugation Based
on Inverse-Electron-Demand Diels-Alder Reactivity. J. Am. Chem. Soc.
130:13518.
Devaraj et al. (2008) Tetrazine-Based Cycloadditions: Application to
Pretargeted Live Cell Imaging. Bioconjugate Chem. 19:2297.
Jena Bioscience GmbH | Löbstedter Str. 80 | 07749 Jena, Germany | Tel.:+49-3641-6285 000 | Fax:+49-3641-6285 100
http://www.jenabioscience.com
Last update: Jun 14, 2013