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Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

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Synonym(s):
DBCO-sulfo-NHS ester, DBCO-sulfo-SE
Empirical Formula (Hill Notation):
C25H21N2NaO8S
Molecular Weight:
532.50
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

240-260 °C

storage temp.

−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

Application

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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