790435
TCO PEG4 succinimidyl ester
Sinônimo(s):
trans-Cyclooctene-PEG4-NHS
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About This Item
Fórmula empírica (Notação de Hill):
C24H38N2O10
Peso molecular:
514.57
Número MDL:
Código UNSPSC:
12352108
ID de substância PubChem:
NACRES:
NA.22
Produtos recomendados
Formulário
liquid
adequação da reação
reaction type: click chemistry
reagent type: linker
grupo funcional
NHS ester
temperatura de armazenamento
−20°C
cadeia de caracteres SMILES
O=C(NCCOCCOCCOCCOCCC(ON1C(CCC1=O)=O)=O)OC2CCC/C=C/CC2
InChI
1S/C24H38N2O10/c27-21-8-9-22(28)26(21)36-23(29)10-12-31-14-16-33-18-19-34-17-15-32-13-11-25-24(30)35-20-6-4-2-1-3-5-7-20/h1-2,20H,3-19H2,(H,25,30)/b2-1+
chave InChI
ZKPMRASGLDBKPF-OWOJBTEDSA-N
Aplicação
Succinimidyl ester/NHS (amine reactive) functionalized trans-cyclooctene derivative for incorporation of the cyclooctene moiety into amine 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 amine to be modified and the reactive alkene.
Código de classe de armazenamento
10 - Combustible liquids
Classe de risco de água (WGK)
WGK 3
Ponto de fulgor (°F)
Not applicable
Ponto de fulgor (°C)
Not applicable
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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
Melissa L Blackman et al.
Journal of the American Chemical Society, 130(41), 13518-13519 (2008-09-19)
Described is a bioorthogonal reaction that proceeds with unusually fast reaction rates without need for catalysis: the cycloaddition of s-tetrazine and trans-cyclooctene derivatives. The reactions tolerate a broad range of functionality and proceed in high yield in organic solvents, water
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