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761524

Sigma-Aldrich

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Sinônimo(s):

DBCO-NHS ester, DBCO-SE

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About This Item

Fórmula empírica (Notação de Hill):
C23H18N2O5
Peso molecular:
402.40
Número MDL:
MFCD24386367
Código UNSPSC:
12352108
ID de substância PubChem:
329766555
NACRES:
NA.22

R$ 783,00

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Formulário

solid

adequação da reação

reaction type: click chemistry
reagent type: cross-linking reagent

pf

149-157 (decomposition)

grupo funcional

NHS ester

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

O=C(CCC(ON(C(CC1)=O)C1=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C23H18N2O5/c26-20(13-14-23(29)30-25-21(27)11-12-22(25)28)24-15-18-7-2-1-5-16(18)9-10-17-6-3-4-8-19(17)24/h1-8H,11-15H2

chave InChI

XCEBOJWFQSQZKR-UHFFFAOYSA-N

Categorias relacionadas

Descrição geral

DBCO-NHS ester is commonly used in bioconjugation. It consists of an NHS ester that reacts with primary amines on biomolecules and an alkyne group that allows for a specific reaction with molecules containing azides. This reaction is carried out through a copper-free click chemistry process called strain-promoted alkyne-azide cycloaddition.[1]

Aplicação

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester is commonly used:
  • In the modification and labeling of biomolecules such as antibodies and streptavidin by introducing DBCO groups onto their surfaces[2]
  • As a cross linker to conjugate peptide antigens onto the surface of poly(lactic-co-glycolic acid) (PLGA) nanoparticles[3]

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
MKCX5454
MKCX3186
MKCW7467
MKCV7905
MKCV7904

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Fleur Kleinpenning et al.
Nature communications, 11(1), 3244-3244 (2020-06-28)
Bioorthogonal chemistry introduces affinity-labels into biomolecules with minimal disruption to the original system and is widely applicable in a range of contexts. In proteomics, immobilized metal affinity chromatography (IMAC) enables enrichment of phosphopeptides with extreme sensitivity and selectivity. Here, we
Graphene Oxide Nanosheets Modified with Single-Domain Antibodies for Rapid and Efficient Capture of Cells.
Chen GY, et al.
Chemistry?A European Journal , 21(48), 17178-17183 (2015)
Hao Ma et al.
Biomaterials, 255, 120205-120205 (2020-06-24)
Three biorthogonal click reactions, a photoinitiated thiol-yne reaction, an azide-alkyne cycloaddition, and a methyltetrazine-transcyclooctene Diels Alder, were used to independently control the presentation of several bioactive proteins to valvular interstitial cells (VICs) in hydrogel scaffolds. Tethered fibroblast growth factor (FGF-2)
Preparation of single-and double-oligonucleotide antibody conjugates and their application for protein analytics
J Wiener, et al.
Scientific reports, 10, 1457-1457 (2020)
Investigating functional DNA grafted on nanodiamond surface using site-directed spin labeling and electron paramagnetic resonance spectroscopy.
Akiel RD., et al.
The Journal of Physical Chemistry B, 120(17), 4003-4008 (2016)
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    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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      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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