Cat#: CCR-0070
(E)-Cyclooct-4-enyl 2,5-dioxo-1-pyrrolidinyl carbonate
Synonyms (s): (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
Empirical Formula (Hill Notation): C13H17NO5
Size: 1 mg; 5 mg
Product Introduction
| Molecular Weight | 267.28 |
| NACRES | NA.22 |
| CAS Number | 1191901-33-3 |
| PubChem Substance ID | 329767127 |
| Form | Solid |
| Reaction Suitability | Reaction type: click chemistry |
| Smiles String | O=C(ON1C(CCC1=O)=O)O[C@@H]2CC/C=C/CCC2 |
| 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 |
| 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.
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.
Safety Information
| Storage Class Code | 11 - Combustible Solids |
| WGK | WGK 3 |
For research use only. Not for clinical use.
