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761982

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-alcohol

for Copper-free Click Chemistry

Sinônimo(s):

Polyethylene glycol, DBCO-PEG4-OH

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About This Item

Fórmula empírica (Notação de Hill):
C29H36N2O6
Peso molecular:
508.61
Código UNSPSC:
51171641
ID de substância PubChem:
329766594
NACRES:
NA.22

Nível de qualidade

100

forma

solid

adequação da reação

reaction type: click chemistry
reagent type: linker

pf

50-60 °C

grupo funcional

hydroxyl

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

InChI

1S/C29H36N2O6/c32-16-18-36-20-22-37-21-19-35-17-15-30-28(33)11-5-6-12-29(34)31-23-26-9-2-1-7-24(26)13-14-25-8-3-4-10-27(25)31/h1-4,7-10,32H,5-6,11-12,15-23H2,(H,30,33)

chave InChI

ZZXWONCQAFVJHM-UHFFFAOYSA-N

Aplicação

Alcohol functionalized cyclooctyne derivative. 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. The PEG spacer adds hydrophilicity to the product to decrease aggregation.

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
MKCM9863
MKCL9444
MKCL0627
MKCH2294
MKBX7305V

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Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions.
Xinghai Ning et al.
Angewandte Chemie (International ed. in English), 47(12), 2253-2255 (2008-02-16)
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
Jeremy M Baskin et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(43), 16793-16797 (2007-10-19)
Dynamic imaging of proteins in live cells is routinely performed by using genetically encoded reporters, an approach that cannot be extended to other classes of biomolecules such as glycans and lipids. Here, we report a Cu-free variant of click chemistry
John C Jewett et al.
Journal of the American Chemical Society, 132(11), 3688-3690 (2010-03-02)
Bioorthogonal chemical reactions, those that do not interact or interfere with biology, have allowed for exploration of numerous biological processes that were previously difficult to study. The reaction of azides with strained alkynes, such as cyclooctynes, readily forms a triazole

Artigos

Copper-Free Click Chemistry

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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