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761982

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-alcohol

for Copper-free Click Chemistry

Synonym(s):

Polyethylene glycol, DBCO-PEG4-OH

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About This Item

Empirical Formula (Hill Notation):
C29H36N2O6
Molecular Weight:
508.61
UNSPSC Code:
51171641
PubChem Substance ID:
329766594
NACRES:
NA.22

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

50-60 °C

functional group

hydroxyl

storage temp.

−20°C

SMILES string

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)

InChI key

ZZXWONCQAFVJHM-UHFFFAOYSA-N

Application

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
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)
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
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

Articles

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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