790443
TCO-PEG3-maleimide
Synonym(s):
trans-Cyclooctene-maleimide
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About This Item
Empirical Formula (Hill Notation):
C26H41N3O8
Molecular Weight:
523.62
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22
eCl@ss:
32150917
form
liquid
Quality Segment
reaction suitability
reaction type: click chemistry, reagent type: linker
technique(s)
targeted protein degradation: suitable
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
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.
Storage Class
10 - Combustible liquids
WGK
WGK 3
Flash Point (°F)
Not applicable
Flash Point (°C)
Not applicable
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