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760749

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-biotin conjugate

for Copper-free Click Chemistry

Synonym(e):

Polyethylene glycol, DBCO-PEG4-biotin

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About This Item

Empirische Formel (Hill-System):
C39H51N5O8S
CAS-Nummer:
Molekulargewicht:
749.92
MDL-Nummer:
UNSPSC-Code:
12352003
PubChem Substanz-ID:
NACRES:
NA.22

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Qualitätsniveau

Form

solid

Eignung der Reaktion

reaction type: click chemistry

Lagertemp.

−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

InChIKey

LNHSQAOQVNHUGL-QRBHCBQLSA-N

Allgemeine Beschreibung

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.

Anwendung

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

Leistungsmerkmale und Vorteile

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Die Dokumentenbibliothek aufrufen

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
Ning, X., et al.
Angewandte Chemie (International Edition in English), 47, 2253-2255 null
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

Artikel

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.

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

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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