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Merck
CN

760749

Dibenzocyclooctyne-PEG4-biotin conjugate

for Copper-free Click Chemistry

Synonym(s):

Polyethylene glycol, DBCO-PEG4-biotin

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About This Item

Empirical Formula (Hill Notation):
C39H51N5O8S
CAS Number:
Molecular Weight:
749.92
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352003
MDL number:
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Quality Level

form

solid

reaction suitability

reaction type: click chemistry

storage temp.

−20°C

SMILES string

O=C(CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12)NCCOCCOCCOCCOCCC(=O)NCCC(=O)N3Cc4ccccc4C#Cc5ccccc35

InChI

1S/C39H51N5O8S/c45-35(12-6-5-11-34-38-32(28-53-34)42-39(48)43-38)41-18-20-50-22-24-52-26-25-51-23-21-49-19-16-36(46)40-17-15-37(47)44-27-31-9-2-1-7-29(31)13-14-30-8-3-4-10-33(30)44/h1-4,7-10,32,34,38H,5-6,11-12,15-28H2,(H,40,46)(H,41,45)(H2,42,43,48)/t32-,34-,38-/m0/s1

InChI key

LNHSQAOQVNHUGL-QRBHCBQLSA-N

General description

This azadibenzocyclooctyne-biotin derivative is a versatile biotinylation reagent for labeling azide containing molecules or compounds. 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. Subsequent labeled molecules can be purified using streptavidin or avidin affinity reagents. The PEG spacer makes the overall compound more hydrophilic and allows for greater distance between the reaction site with the azide and the biotin detecting group.

Application

Automate your Biotin tagging with Synple Automated Synthesis Platform (SYNPLE-SC002)

Features and Benefits

More efficient labeling will occur at higher temperatures and with greater excess of biotin reagent. Typical reaction times are up to 4 hours, but longer incubation periods should be used if concentration is low or if low labeling is observed. Product is most efficient when first dissolved in a water miscible organic solvent and then diluted in aqueous reaction buffer when needed. DBCO-PEG4-Biotin is soluble in aqueous buffers up to 0.35 mM.


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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Articles

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

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 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
Guillaume Charron et al.
Journal of the American Chemical Society, 131(13), 4967-4975 (2009-03-14)
Fatty-acylation of proteins in eukaryotes is associated with many fundamental cellular processes but has been challenging to study due to limited tools for rapid and robust detection of protein fatty-acylation in cells. The development of azido-fatty acids enabled the nonradioactive
Andrew Vila et al.
Chemical research in toxicology, 21(2), 432-444 (2008-02-01)
Polyunsaturated fatty acids (PUFA) are primary targets of free radical damage during oxidative stress. Diffusible electrophilic alpha,beta-unsaturated aldehydes, such as 4-hydroxynonenal (HNE), have been shown to modify proteins that mediate cell signaling (e.g., IKK and Keap1) and alter gene expression



Global Trade Item Number

SKUGTIN
760749-5MG04061833565254