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760676 Sigma-Aldrich

Dibenzocyclooctyne-PEG4-maleimide

for Copper-free Click Chemistry

Synonym: DBCO-PEG4-maleimide

  • Empirical Formula (Hill Notation) C36H42N4O9

  • Molecular Weight 674.74

  •  MDL number MFCD22572659

  •  PubChem Substance ID 329766888

  •  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,
storage temp.   −20°C
SMILES string   O=C(CCOCCOCCOCCOCCNC(=O)CCN1C(=O)C=CC1=O)NCCC(=O)N2Cc3ccccc3C#Cc4ccccc24
InChI   1S/C36H42N4O9/c41-32(14-18-39-34(43)11-12-35(39)44)38-17-20-47-22-24-49-26-25-48-23-21-46-19-15-33(42)37-16-13-36(45)40-27-30-7-2-1-5-28(30)9-10-29-6-3-4-8-31(29)40/h1-8,11-12H,13-27H2,(H,37,42)(H,38,41)
InChI key   VVFZXPZWVJMYPX-UHFFFAOYSA-N

Description

Application

Maleimide functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into thiol 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 PEG lipophilic spacer helps to reduce aggregation and precipitation problems when labeling biomolecules.
Applications Include:
• Protein-peptide conjugates
• Antibody-enzyme or antibody-drug conjugates
• Protein or peptide-oligonucleotide conjugates
• Surface modification

Packaging

1, 5, 50 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

Polyethylene Glycol (PEG) Selection Guide

Poly(ethylene glycol) (PEG) is a synthetic, hydrophilic, biocompatible polymer with widespread use in biomedical and other applications. PEGs are synthesized using a ring-opening polymerization of et...
Keywords: Adhesion, Bacterial conjugations, Click chemistry, Molecular biology, PEGylations, Polymerization reactions, Ring-opening polymerization

Peer-Reviewed Papers
15

References

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