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761516

Sigma-Aldrich

Dibenzocyclooctinsäure

95%, storage temp.:-20°C

Synonym(e):

DBCO-Säure

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About This Item

Empirische Formel (Hill-System):
C21H19NO3
Molekulargewicht:
333.38
MDL-Nummer:
UNSPSC-Code:
12352106
PubChem Substanz-ID:
NACRES:
NA.22

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Qualitätsniveau

Assay

95%

Form

solid

Eignung der Reaktion

reaction type: click chemistry
reagent type: linker

mp (Schmelzpunkt)

118-125 °C

Funktionelle Gruppe

carboxylic acid

Lagertemp.

−20°C

SMILES String

O=C(CCCCC(O)=O)N1CC2=C(C=CC=C2)C#CC3=C1C=CC=C3

InChI

1S/C21H19NO3/c23-20(11-5-6-12-21(24)25)22-15-18-9-2-1-7-16(18)13-14-17-8-3-4-10-19(17)22/h1-4,7-10H,5-6,11-12,15H2,(H,24,25)

InChIKey

NIRLBCOFKPVQLM-UHFFFAOYSA-N

Allgemeine Beschreibung

Azid-funktionalisiertes Cyclooctin-Derivat. Cyclooctine sind nützlich bei Stamm-vermittelten kupferfreien Azid-Alkin-Click-Chemie-Reaktionen. Dieses Azadibenzocyclooktin reagiert ohne Cu(I)-Katalysator mit Azid-funktionalisierten Verbindungen oder Biomolekülen, um eine stabile Triazolverbindung zu erzeugen.

Anwendung

Dibenzocyclooctinsäure kann zur Oberflächenmodifizierung von achtarmigem Poly(ethylenglycol) eingesetzt werden, um es empfänglich für Stamm-vermittelte Alkin-Azid-Cycloaddition (SPAAC) zu machen, wobei PEG-bis-Azid zur Bildung von Hydrogelen führt. Diese Hydrogele sind nützlich für die Proteinimmobilisierung.[1]

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

Chen Guo et al.
Acta biomaterialia, 56, 80-90 (2017-04-10)
Hydrogels are facile architectures for the controlled presentation of proteins with far-reaching applications, from fundamental biological studies in three-dimensional culture to new regenerative medicine and therapeutic delivery strategies. Here, we demonstrate a versatile approach for spatially-defined presentation of engineered proteins
Ratiometric Fluorescence Azide?Alkyne Cycloaddition for Live Mammalian Cell Imaging.
Fu H, et al.
Analytical Chemistry, 87(22), 11332-11336 (2015)
Seyed Mohammad Mahdi Dadfar et al.
Small (Weinheim an der Bergstrasse, Germany), 14(21), e1800131-e1800131 (2018-04-24)
Different types of click chemistry reactions are proposed and used for the functionalization of surfaces and materials, and covalent attachment of organic molecules. In the present work, two different catalyst-free click approaches, namely azide-alkyne and thiol-alkyne click chemistry are studied
Flexible synthesis of cationic peptide?porphyrin derivatives for light-triggered drug delivery and photodynamic therapy.
Dondi R, et al.
Organic & Biomolecular Chemistry, 14(48), 11488-11501 (2016)
Bio-orthogonal conjugation and enzymatically triggered release of proteins within multi-layered hydrogels.
Guo C, et al.
Acta Biomaterialia (2017)

Questions

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  1. 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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  2. 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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