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
form
liquid
Quality Level
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
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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René Platzer et al.
Nature communications, 11(1), 4993-4993 (2020-10-07)
Determining nanoscale protein distribution via Photoactivated Localization Microscopy (PALM) mandates precise knowledge of the applied fluorophore's blinking properties to counteract overcounting artifacts that distort the resulting biomolecular distributions. Here, we present a readily applicable methodology to determine, optimize and quantitatively
Mark R Karver et al.
Bioconjugate chemistry, 22(11), 2263-2270 (2011-09-29)
1,2,4,5-Tetrazines have been established as effective dienes for inverse electron demand [4 + 2] Diels-Alder cycloaddition reactions with strained alkenes for over 50 years. Recently, this reaction pair combination has been applied to bioorthogonal labeling and cell detection applications; however
Neal K Devaraj et al.
Bioconjugate chemistry, 19(12), 2297-2299 (2008-12-05)
Bioorthogonal tetrazine cycloadditions have been applied to live cell labeling. Tetrazines react irreversibly with the strained dienophile norbornene forming dihydropyrazine products and dinitrogen. The reaction is high yielding, selective, and fast in aqueous media. Her2/neu receptors on live human breast
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 790443-25MG | 04061833231982 |
| 790443-5MG | 04061833231999 |