764523

(E)-Cyclooct-4-enyl 2,5-dioxo-1-pyrrolidinyl carbonate

• Sinonimo/i: (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
• Formula empirica (notazione di Hill): C₁₃H₁₇NO₅
• Numero CAS: 1191901-33-3
• Peso molecolare: 267.28
• Codice UNSPSC: 12352200
• ID PubChem: 329767127
• NACRES: NA.22

Proprietà

• Stato: solid
• Livello qualitativo: 100
• Impiego in reazioni chimiche: reaction type: click chemistry; reagent type: linker
• Punto di fusione: 90-105 °C
• Gruppo funzionale: NHS ester
• Temperatura di conservazione: −20°C
• Stringa SMILE: 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; OUGQJOKGFAIFAQ-TXXBHVLJSA-N

Descrizione

Applicazioni

(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.

Informazioni sulla sicurezza

• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable