Merck
All Photos(3)

760676

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-maleimide

for Copper-free Click Chemistry

Synonym(s):
DBCO-PEG4-maleimide
Empirical Formula (Hill Notation):
C36H42N4O9
Molecular Weight:
674.74
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

solid

reaction suitability

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

storage temp.

−20°C

SMILES string

O=C(CCNC(CCOCCOCCOCCOCCNC(CCN1C(C=CC1=O)=O)=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

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

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

Ning, X., et al.
Angewandte Chemie (International Edition in English), 47, 2253-2255 null
Efficient cargo delivery into adult brain tissue using short cell-penetrating peptides
Kizil C, et al.
PLoS ONE, 10(4), e0124073-e0124073 (2015)
Nano-scale alignment of proteins on a flexible DNA backbone.
Nojima T, et al.
PLoS ONE, 7(12), e52534-e52534 (2012)
Xiaowen Liu et al.
Biomacromolecules, 17(1), 173-182 (2015-12-15)
Intracellularly-acting therapeutic proteins are considered promising alternatives for the treatment of various diseases. Major limitations of their application are low efficiency of intracellular delivery and possible reduction of protein activity during derivatization. Herein, we report pH-sensitive covalent modification of proteins
Lutz Nuhn et al.
Bioconjugate chemistry, 29(7), 2394-2405 (2018-06-12)
Tumor-associated macrophages (TAMs) with high expression levels of the Macrophage Mannose Receptor (MMR, CD206) exhibit a strong angiogenic and immune suppressive activity. Thus, they are a highly attractive target in cancer immunotherapy, with the aim to modulate their protumoral behavior.

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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