764523

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

• Synonyme(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
• Formule empirique (notation de Hill): C₁₃H₁₇NO₅
• Numéro CAS: 1191901-33-3
• Poids moléculaire : 267.28
• Code UNSPSC : 12352200
• ID de substance PubChem : 329767127
• Nomenclature NACRES : NA.22

Propriétés

• Forme: solid
• Niveau de qualité: 100
• Capacité de réaction: reaction type: click chemistry
• Pertinence de la réaction: reagent type: linker
• Pf: 90-105 °C
• Groupe fonctionnel: NHS ester
• Température de stockage: −20°C
• Chaîne SMILES: 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
• Clé InChI: OUGQJOKGFAIFAQ-TXXBHVLJSA-N

Description

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable