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761516

Sigma-Aldrich

Dibenzocyclooctyne-acid

95%, storage temp.:-20°C

Synonym(s):

DBCO-Acid

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About This Item

Empirical Formula (Hill Notation):
C21H19NO3
Molecular Weight:
333.38
MDL number:
MFCD22380737
UNSPSC Code:
12352106
PubChem Substance ID:
329766553
NACRES:
NA.22

CN¥3,913.36

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Assay

95%

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

118-125 °C

functional group

carboxylic acid

storage temp.

−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)

InChI key

NIRLBCOFKPVQLM-UHFFFAOYSA-N

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shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

shipped in

-

storage temp.

−70°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100, 200

General description

Acid functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne click chemistry reactions. This azadibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage.

Application

Dibenzocyclooctyne-acid may be used for the surface modification of eight-arm poly(ethylene glycol), to make it susceptible to strain promoted alkyne-azide cycloaddition (SPAAC) with PEG-bis-azide leading to the formation of hydrogels. These hydrogels are useful for protein immobilization.[1]

Storage Class Code

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
    MKCW1169
    MKCV8729
    MKCT5198
    MKCS1612
    MKCQ4866

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    Ratiometric Fluorescence Azide?Alkyne Cycloaddition for Live Mammalian Cell Imaging.
    Fu H, et al.
    Analytical Chemistry, 87(22), 11332-11336 (2015)
    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
    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)
    View All Related Papers

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