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Sigma-Aldrich

Dibenzocyclooctyne-maleimide

for Copper-free Click Chemistry

Synonym(s):

DBCO-maleimide

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About This Item

Empirical Formula (Hill Notation):
C25H21N3O4
Molecular Weight:
427.45
MDL number:
MFCD22380750
UNSPSC Code:
12352111
PubChem Substance ID:
329766887
NACRES:
NA.22

Quality Level

100

form

solid

reaction suitability

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

functional group

maleimide

storage temp.

−20°C

SMILES string

O=C(N1CCC(NCCC(N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4)=O)=O)C=CC1=O

InChI

1S/C25H21N3O4/c29-22(14-16-27-23(30)11-12-24(27)31)26-15-13-25(32)28-17-20-7-2-1-5-18(20)9-10-19-6-3-4-8-21(19)28/h1-8,11-12H,13-17H2,(H,26,29)

InChI key

NHFQNAGPXIVKND-UHFFFAOYSA-N

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.

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

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H400

Precautionary Statements

P273

Hazard Classifications

Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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A comparative study of bioorthogonal reactions with azides
Agard, N.; et al.
ACS Chemical Biology, 10, 644-648 (2006)
Highly robust and optimized conjugation of antibodies to nanoparticles using quantitatively validated protocols.
Jeong S, et al.
Nanoscale, 9(7), 2548-2555 (2017)
Site-selective installation of BASHY fluorescent dyes to Annexin V for targeted detection of apoptotic cells
Cal PM, et al.
Chemical Communications (Cambridge, England), 53(2), 368-371 (2017)
Hansjörg Götzke et al.
Nature communications, 10(1), 4403-4403 (2019-09-29)
Specialized epitope tags are widely used for detecting, manipulating or purifying proteins, but often their versatility is limited. Here, we introduce the ALFA-tag, a rationally designed epitope tag that serves a remarkably broad spectrum of applications in life sciences while
Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions.
Xinghai Ning et al.
Angewandte Chemie (International ed. in English), 47(12), 2253-2255 (2008-02-16)
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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.

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