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761532 Sigma-Aldrich

Dibenzocyclooctyne-S-S-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym: DBCO-S-S-succinimidyl ester, DBCO-S-S-NHS ester, DBCO-S-S-SE

  • Empirical Formula (Hill Notation) C28H27N3O6S2

  • Molecular Weight 565.66

  •  MDL number MFCD22380758

  •  PubChem Substance ID 329766556

  •  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   192-197 °C
storage temp.   −20°C
SMILES string   O=C(CCC(=O)N1Cc2ccccc2C#Cc3ccccc13)NCCSSCCC(=O)ON4C(=O)CCC4=O
InChI   1S/C28H27N3O6S2/c32-24(29-16-18-39-38-17-15-28(36)37-31-26(34)13-14-27(31)35)11-12-25(33)30-19-22-7-2-1-5-20(22)9-10-21-6-3-4-8-23(21)30/h1-8H,11-19H2,(H,29,32)
InChI key   RPNGUSKTYYIUDE-UHFFFAOYSA-N

Description

Application

Cleavable 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. The disulfide present can be readily cleaved using mild reducing conditions (10-50 mM DTT at 37°C for 30 min or 5% ß-mercaptoethanol in SDS-PAGE sample buffer at 100°C for 5 minutes).

Caution: Please avoid reducing agents and amine or azide containing buffers during coupling/labeling reactions. Only use reducing agents when cleavage of the disulfide is desired.

Packaging

1 mg in amber 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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Certificate of Origin (COO)

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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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