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790435

Sigma-Aldrich

TCO PEG4 succinimidyl ester

Synonym(s):

trans-Cyclooctene-PEG4-NHS

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About This Item

Empirical Formula (Hill Notation):
C24H38N2O10
Molecular Weight:
514.57
MDL number:
MFCD28118912
UNSPSC Code:
12352108
PubChem Substance ID:
329768214
NACRES:
NA.22
Pricing and availability is not currently available.

form

liquid

Quality Level

100

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

NHS ester

storage temp.

−20°C

SMILES string

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+

InChI key

ZKPMRASGLDBKPF-OWOJBTEDSA-N

Related Categories

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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV7994
MKCQ2539
MKCP0138
MKCH3643
MKCB6989

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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
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

Questions

  1. 790435 This material can exist as both the axial and equatorial isomer. Please indicate which isomer this product represents. Thanks.

    1 answer

    1. This product is sold as a racemate. Unfortunately, there is no indication of its preferred conformation. Product 764523 is an enantiopure compound supplied as a single equatorial diastereomer (major, rel-(1S-2S-5E-pR)). Please see the link below to review this product:
      https://www.sigmaaldrich.com/US/en/product/aldrich/764523

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