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761524 Sigma-Aldrich

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym: DBCO-NHS ester, DBCO-SE

  • Empirical Formula (Hill Notation) C23H18N2O5

  • Molecular Weight 402.40

  •  MDL number MFCD24386367

  •  PubChem Substance ID 329766555

  •  NACRES NA.22

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Properties

Related Categories Chemical Biology, Chemical Synthesis, Conjugation Chemistry: Azides, Alkynes and Other Reagents, Copper-Free Click Chemistry, Crosslinkers,
Quality Level   100
mp   149-157 (decomposition)
storage temp.   −20°C
SMILES string   O=C(CCC(=O)N1Cc2ccccc2C#Cc3ccccc13)ON4C(=O)CCC4=O
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

Description

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

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Copper-Free Click Chemistry

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.1 The absence of exogenous me...
Keywords: 1,3-Dipolar cycloaddition, Catalysis, Click chemistry, Cycloadditions, Pharmaceutical, Positron Emission Tomography

Peer-Reviewed Papers
15

References

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