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Merck
CN

760668

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

Key Documents

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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

Related Categories

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW1170
MKCW5477
MKCT1472
MKCR9310
MKCR5605

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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)
A comparative study of bioorthogonal reactions with azides
Agard, N.; et al.
ACS Chemical Biology, 10, 644-648 (2006)
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
Sebastian Strauss et al.
Nature methods, 17(8), 789-791 (2020-07-01)
DNA-PAINT's imaging speed has recently been significantly enhanced by optimized sequence design and buffer conditions. However, this implementation has not reached an ultimate speed limit and is only applicable to imaging of single targets. To further improve acquisition speed, we
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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.

无铜点击化学

无铜点击化学是点击化学的一种替代方法，可在较低的活化屏障下进行，且没有细胞毒性过渡金属催化剂。

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