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790443

Sigma-Aldrich

TCO-PEG3-maleimide

Synonym(s):

trans-Cyclooctene-maleimide

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About This Item

Empirical Formula (Hill Notation):
C26H41N3O8
Molecular Weight:
523.62
UNSPSC Code:
12352111
PubChem Substance ID:
329768215
NACRES:
NA.22

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

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.

related product

Product No.
Description
Pricing

924083

TAMRA-a-TCO

924091

Alkyne-a-TCO

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
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
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

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