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
• UNSPSC Code: 12352200
• PubChem Substance ID: 329767127
• NACRES: NA.22

Properties

• form: solid
• reaction suitability: reaction type: click chemistry; reagent type: linker
• 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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable