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760676

Dibenzocyclooctyne-PEG4-maleimide

for Copper-free Click Chemistry

Synonym(s):

Polyethylene glycol, DBCO-PEG4-maleimide

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About This Item

Empirical Formula (Hill Notation):
C36H42N4O9
Molecular Weight:
674.74
NACRES:
NA.22
PubChem Substance ID:
329766888
UNSPSC Code:
12161502
MDL number:
MFCD22572659
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form

solid

reaction suitability

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

functional group

maleimide

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

Storage Class

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
MKCV6020
MKCT3586
MKCS5655
MKCN2592
MKCR1149

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Articles

Click Chemistry in Drug Discovery

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

Click Chemistry in Drug Discovery

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

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.

View All Articles
Ning, X., et al.
Angewandte Chemie (International Edition in English), 47, 2253-2255 null
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
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Global Trade Item Number

SKUGTIN
760676-50MG04061832918037
760676-5MG04061833230480
760676-1MG04061826701591