761982

Dibenzocyclooctyne-PEG4-alcohol

Name: Dibenzocyclooctyne-PEG4-alcohol
Brand: ALDRICH
Price: 78 USD
Availability: InStock

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

Key Documents

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Product Name

Dibenzocyclooctyne-PEG4-alcohol, for Copper-free Click Chemistry

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

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

50-60 °C

functional group

hydroxyl

storage temp.

−20°C

Quality Level

100

Related Categories

Chemical Biology

Click Chemistry Reagents Overview

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Show Differences

1 of 4

This Item	759902	760676	764019
Sigma-Aldrich 761982 Dibenzocyclooctyne-PEG4-alcohol	Sigma-Aldrich 759902 Dibenzocyclooctyne-PEG4-acid	Sigma-Aldrich 760676 Dibenzocyclooctyne-PEG4-maleimide	Sigma-Aldrich 764019 Dibenzocyclooctyne-PEG4-N-hydroxysuccinimidyl ester
form solid	form solid	form solid	form paste
functional group hydroxyl	functional group carboxylic acid	functional group maleimide	functional group NHS ester
Quality Level 100	Quality Level 100	Quality Level -	Quality Level 100
reaction suitability reaction type: click chemistry, reagent type: linker	reaction suitability reaction type: click chemistry, reagent type: linker	reaction suitability reaction type: click chemistry, reagent type: cross-linking reagent	reaction suitability reaction type: click chemistry, reagent type: linker
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
mp 50-60 °C	mp -	mp -	mp -

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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A comparative study of bioorthogonal reactions with azides.

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)

Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones.

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

Copper-free click chemistry for dynamic in vivo imaging.

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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Dibenzocyclooctyne-PEG4-alcohol