761524

Sigma-Aldrich

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym(s):
DBCO-SE, DBCO-NHS ester
Empirical Formula (Hill Notation):
C23H18N2O5
Molecular Weight:
402.40
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

reaction suitability

reaction type: click chemistry
reagent type: cross-linking reagent

mp

149-157 (decomposition)

storage temp.

−20°C

SMILES string

O=C(CCC(ON(C(CC1)=O)C1=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C23H18N2O5/c26-20(13-14-23(29)30-25-21(27)11-12-22(25)28)24-15-18-7-2-1-5-16(18)9-10-17-6-3-4-8-19(17)24/h1-8H,11-15H2

InChI key

XCEBOJWFQSQZKR-UHFFFAOYSA-N

Application

Succinimidyl ester (NHS, amine reactive) functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. Cyclooctynes are useful in strain-promoted copper-free click chemistry 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.

Applications Include:
  • Protein-peptide conjugates
  • Antibody-enzyme or antibody-drug conjugates
  • Protein or peptide-oligonucleotide conjugates
  • Surface modification

Packaging

1, 5, 50 mg in clear glass bottle

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

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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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