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760706 Sigma-Aldrich

Sulfo-dibenzocyclooctyne-biotin conjugate

for Copper-free Click Chemistry

Synonym: Sulfo-DBCO-biotin

  • Empirical Formula (Hill Notation) C37H50N6O7S2

  • Molecular Weight 754.96

  •  PubChem Substance ID 329766890

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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
storage temp.   −20°C
SMILES string   CC[NH+](CC)CC.[O-]S(=O)(=O)C(CNC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12)C(=O)NCCC(=O)N3Cc4ccccc4C#Cc5ccccc35
InChI   1S/C31H35N5O7S2.C6H15N/c37-27(12-6-5-11-25-29-23(19-44-25)34-31(40)35-29)33-17-26(45(41,42)43)30(39)32-16-15-28(38)36-18-22-9-2-1-7-20(22)13-14-21-8-3-4-10-24(21)36;1-4-7(5-2)6-3/h1-4,7-10,23,25-26,29H,5-6,11-12,15-19H2,(H,32,39)(H,33,37)(H2,34,35,40)(H,41,42,43);4-6H2,1-3H3/t23-,25-,26?,29-;/m0./s1
InChI key   RACLEVCKGUBCTH-GESOYTMLSA-N

Description

General description

This sulfonated azadibenzocyclooctyne-biotin derivative is a highly water soluble and versatile biotinylation reagent for labeling azide containing molecules or compounds. 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. Subsequent labeled molecules can be purified using streptavidin or avidin affinity reagents.

Packaging

5 mg in amber glass bottle

Application

• activity-based protein profiling
• detection of newly synthesized proteins
• immobilization of azide-labeled biomolecules

Features and Benefits

More efficient labeling will occur at higher temperatures and with greater excess of biotin reagent. Typical reaction times are up to 4 hours, but longer incubation periods should be used if concentration is low or if low labeling is observed. Product is most efficient when first dissolved in a water miscible organic solvent and then diluted in aqueous reaction buffer when needed. Stock solutions in DMSO have been shown to be stable in the freezer for up to 3 months.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
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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