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790435

Sigma-Aldrich

TCO PEG4 succinimidyl ester

Synonyme(s) :

trans-Cyclooctene-PEG4-NHS

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About This Item

Formule empirique (notation de Hill):
C24H38N2O10
Poids moléculaire :
514.57
Numéro MDL:
MFCD28118912
Code UNSPSC :
12352108
ID de substance PubChem :
329768214
Nomenclature NACRES :
NA.22

Forme

liquid

Capacité de réaction

reaction type: click chemistry

Pertinence de la réaction

reagent type: linker

Groupe fonctionnel

NHS ester

Température de stockage

−20°C

Chaîne 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+

Clé InChI

ZKPMRASGLDBKPF-OWOJBTEDSA-N

Application

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.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

924083

TAMRA-a-TCO

924091

Alkyne-a-TCO

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Dave Lumen et al.
Pharmaceutics, 11(12) (2019-12-22)
Polyethylene glycol (PEG) has been successfully used for improving circulation time of several nanomaterials but prolonging the circulation of porous silicon nanoparticles (PSi NPs) has remained challenging. Here, we report a site specific radiolabeling of dual-PEGylated thermally oxidized porous silicon
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
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
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

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