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762040

Sigma-Aldrich

Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Sinonimo/i:

DBCO-sulfo-NHS ester, DBCO-sulfo-SE

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About This Item

Formula empirica (notazione di Hill):
C25H21N2NaO8S
Peso molecolare:
532.50
Numero MDL:
Codice UNSPSC:
12352108
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

≥90.0 %

Stato

solid

Impiego in reazioni chimiche

reaction type: click chemistry
reagent type: linker

P. ebollizione

30 -100 °C

Punto di fusione

240-260 °C

Solubilità

water: soluble at 20 °C

Temperatura di conservazione

−20°C

Stringa SMILE

O=C(CCCCC(ON(C(CC1S(=O)(O[Na])=O)=O)C1=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C25H22N2O8S.Na/c28-22(11-5-6-12-24(30)35-27-23(29)15-21(25(27)31)36(32,33)34)26-16-19-9-2-1-7-17(19)13-14-18-8-3-4-10-20(18)26;/h1-4,7-10,21H,5-6,11-12,15-16H2,(H,32,33,34);/q;+1/p-1
QXKHPYSXPCJSPR-UHFFFAOYSA-M

Applicazioni

Water soluble succinimidyl ester/NHS functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This dibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage.
Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester may be used for the covalent modification of nano-sized metal-organic frameworks (NMOFs) with nucleic acids via click chemistry during the synthesis stimuli-responsive DNA-gated NMOFs. These NMOFs can act as carriers of a fluorescent agent or anticancer drug, making them highly useful in targeted drug release system.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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Hyun Jong Lee et al.
Advanced healthcare materials, 7(19), e1800560-e1800560 (2018-08-15)
In this study, an in situ forming corneal stromal substitute based on collagen type I crosslinked by bio-orthogonal strain-promoted azide-alkyne cycloaddition (SPAAC) is presented. The crosslinked collagen gel has greater transparency compared to non-crosslinked collagen gels. The mechanical properties of
Switchable supramolecular catalysis using DNA-templated scaffolds.
Garcia MAA, et al.
Chemical Communications (Cambridge, England), 52(10), 2153-2156 (2016)
Optically Transparent Dense Colloidal Gels.
Zupkauskas M, et al.
Chemical Science (2017)
ATP?Responsive Aptamer?Based Metal?Organic Framework Nanoparticles (NMOFs) for the Controlled Release of Loads and Drugs.
Chen WH, et al.
Advances in Functional Materials (2017)
Ning, X., et al.
Angewandte Chemie (International Edition in English), 47, 2253-2255 null

Articoli

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.

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