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Documenti fondamentali

760749

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-biotin conjugate

for Copper-free Click Chemistry

Sinonimo/i:

Polyethylene glycol, DBCO-PEG4-biotin

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About This Item

Formula empirica (notazione di Hill):
C39H51N5O8S
Numero CAS:
Peso molecolare:
749.92
Numero MDL:
Codice UNSPSC:
12352003
ID PubChem:
NACRES:
NA.22

Stato

solid

Impiego in reazioni chimiche

reaction type: click chemistry

Temperatura di conservazione

−20°C

Stringa SMILE

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
LNHSQAOQVNHUGL-QRBHCBQLSA-N

Descrizione generale

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.

Applicazioni

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

Caratteristiche e vantaggi

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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Ning, X., et al.
Angewandte Chemie (International Edition in English), 47, 2253-2255 null
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
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
Daniela C Dieterich et al.
Nature protocols, 2(3), 532-540 (2007-04-05)
A major aim of proteomics is the identification of proteins in a given proteome at a given metabolic state. This protocol describes the step-by-step labeling, purification and detection of newly synthesized proteins in mammalian cells using the non-canonical amino acid
Nicholas J Agard et al.
ACS chemical biology, 1(10), 644-648 (2006-12-19)
Detection of metabolites and post-translational modifications can be achieved using the azide as a bioorthogonal chemical reporter. Once introduced into target biomolecules, either metabolically or through chemical modification, the azide can be tagged with probes using one of three highly

Articoli

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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