764523

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

• Synonym(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
• CAS Number: 1191901-33-3
• Molecular Weight: 267.28
• PubChem Substance ID: 329767127
• NACRES: NA.22

Properties

• form: solid
• Quality Level: 100
• reaction suitability: reaction type: click chemistry; reagent type: cross-linking reagent
• mp: 90-105 °C
• functional group: NHS ester
• storage temp.: −20°C
• 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

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.

Packaging

1, 5, 25 mg in amber glass bottle

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable