790443

TCO-PEG3-maleimide

• Synonym(s): trans-Cyclooctene-maleimide
• Empirical Formula (Hill Notation): C₂₆H₄₁N₃O₈
• Molecular Weight: 523.62
• UNSPSC Code: 12352111
• PubChem Substance ID: 329768215
• NACRES: NA.22

Properties

• form: liquid
• reaction suitability: reaction type: click chemistry; reagent type: linker
• functional group: maleimide
• storage temp.: −20°C
• SMILES string: O=C(NCCCOCCOCCOCCCNC(CCN1C(C=CC1=O)=O)=O)OC2CCC/C=C/CC2
• InChI: 1S/C26H41N3O8/c30-23(12-15-29-24(31)10-11-25(29)32)27-13-6-16-34-18-20-36-21-19-35-17-7-14-28-26(33)37-22-8-4-2-1-3-5-9-22/h1-2,10-11,22H,3-9,12-21H2,(H,27,30)(H,28,33)/b2-1+
• InChI key: BJZRPWAVCDJCTC-OWOJBTEDSA-N

Description

Biochem/physiol Actions

Maleimide (thiol reactive) functionalized trans-cyclooctene derivative for incorporation of the cyclooctene moiety into thiol containing compounds or biomolecules. Trans-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. The PEG spacer allows for increased water solubility; less aggregation and an increased distance between the thiol to be modified and the reactive alkene.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable