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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
790435
TCO PEG4 succinimidyl ester
Synonym(s):
trans-Cyclooctene-PEG4-NHS
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5 MG
¥37,400
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¥90,600
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5 MG
¥37,400
25 MG
¥90,600
About This Item
Empirical Formula (Hill Notation):
C24H38N2O10
Molecular Weight:
514.57
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
form
liquid
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
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.
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Listings
Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.
JAN Code
790435-VAR:
790435-BULK:
790435-5MG:
790435-25MG:
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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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790435 This material can exist as both the axial and equatorial isomer. Please indicate which isomer this product represents. Thanks.
1 answer-
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