Synonym: (E)-4-Cycloocten-1-yl 2,5-dioxo-1-pyrrolidinyl ester carbonic acid; trans-4-Cycloocten-1-yl 2,5-dioxo-1-pyrrolidinyl carbonate; TCO-N-hydroxysuccinimidyl carbonate; TCO-NHS; TCO-carbonate
CAS Number: 1191901-33-3
Empirical Formula (Hill Notation): C13H17NO5
Molecular Weight: 267.28
Linear Formula: C13H17NO5
Product Type: Chemical
| form |
solid |
| functional group |
NHS ester |
| InChI |
1S/C13H17NO5/c15-11-8-9-12(16)14(11)19-13(17)18-10-6-4-2-1-3-5-7-10/h1-2,10H,3-9H2/b2-1+/t10-/m1/s1 |
| InChI key |
OUGQJOKGFAIFAQ-TXXBHVLJSA-N |
| mp |
90-105 °C |
| Quality Level |
100  |
| reaction suitability |
reaction type: click chemistry |
| |
reagent type: linker |
| SMILES string |
O=C(ON1C(CCC1=O)=O)O[C@@H]2CC/C=C/CCC2 |
| storage temp. |
−20°C |
| Application: |
(E)-Cyclooct-4-enyl 2,5-dioxo-1-pyrrolidinyl carbonate may be used in the synthesis of vancomycin-TCO that can bind to the cell wall of gram-positive bacteria, which can subsequently react with tetrazine (Tz) decorated magneto-fluorescent nanoparticles orthogonally. This bioorthogonal labeling method is useful for the detection of gram-positive bacteria. |
| Application: |
Succinimidyl carbonate/NHS functionalized cyclooctene derivative for incorporation of the cyclooctene moiety into amine containing compounds or biomolecules. Cyclooctenes are useful in strain-promoted copper-free click chemistry cycloaddition reactions with 1,2,4,5-tetrazines. This cyclooctene will react with tetrazine functionalized compounds or biomolecules without the need for a catalyst to result in a stable covalent linkage. The 4+2 inverse electron demand Diels-Alder cycloaddition between trans-cyclooctene and tetrazines is the fastest biologically compatible ligation technology reported and has had many applications in biological labeling and imaging. |
| Packaging: |
1, 5, 25 mg in amber glass bottle |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| mp |
90-105 °C |
| Storage Temp. |
−20°C |
| UNSPSC |
12352200 |
