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Merck
모든 사진(1)

주요 문서

762040

Sigma-Aldrich

Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

동의어(들):

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

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About This Item

실험식(Hill 표기법):
C25H21N2NaO8S
Molecular Weight:
532.50
MDL number:
UNSPSC 코드:
12352108
PubChem Substance ID:
NACRES:
NA.22

Quality Level

형태

solid

반응 적합성

reaction type: click chemistry
reagent type: linker

mp

240-260 °C

저장 온도

−20°C

SMILES string

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

InChI key

QXKHPYSXPCJSPR-UHFFFAOYSA-M

애플리케이션

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable


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문서 라이브러리 방문

Switchable supramolecular catalysis using DNA-templated scaffolds.
Garcia MAA, et al.
Chemical Communications (Cambridge, England), 52(10), 2153-2156 (2016)
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)
Optically Transparent Dense Colloidal Gels.
Zupkauskas M, et al.
Chemical Science (2017)
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
Instructing cells with programmable peptide DNA hybrids.
Freeman R, et al.
Nature Communications, 8 (2017)

문서

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.

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

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