Skip to Content
Merck
All Photos(1)

Documents

759902

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-acid

for Copper-free Click Chemistry

Synonym(s):

Polyethylene glycol, DBCO-PEG4-Acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C32H40N2O8
Molecular Weight:
580.67
MDL number:
MFCD22380749
UNSPSC Code:
12352106
PubChem Substance ID:
329766822
NACRES:
NA.22

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

carboxylic acid

storage temp.

−20°C

SMILES string

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

InChI

1S/C32H40N2O8/c35-30(33-16-18-40-20-22-42-24-23-41-21-19-39-17-15-32(37)38)11-5-6-12-31(36)34-25-28-9-2-1-7-26(28)13-14-27-8-3-4-10-29(27)34/h1-4,7-10H,5-6,11-12,15-25H2,(H,33,35)(H,37,38)

InChI key

RMYANOWYMFCGGS-UHFFFAOYSA-N

Application

Acid 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.
Dibenzocyclooctyne-PEG4-acid may be used as a substrate in azide-cyclooctyne cycloaddition reactions.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Bioorthogonal Reaction Pairs Enable Simultaneous, Selective, Multi?Target Imaging
Karver MR, et al.
Angewandte Chemie (International Edition in English), 51(4), 920-922 (2012)
Selvanathan Arumugam et al.
Bioorganic & medicinal chemistry letters, 21(23), 6987-6991 (2011-10-26)
N-Terminally azido-modified peptides were labeled with the novel prosthetic labeling synthon [(18)F]azadibenzocyclooctyne ([(18)F]ADIBO) using copper-free azide-alkyne [3+2]-dipolar cycloaddition in high radiochemical yields (RCYs). (18)F-Labeled [(18)F]ADIBO was prepared by nucleophilic substitution of the corresponding tosylate in 21% overall RCY (EOB) in
Jianwen Xu et al.
Chemistry, an Asian journal, 6(10), 2730-2737 (2011-09-29)
Strategies to encapsulate cells in cytocompatible three-dimensional hydrogels with tunable mechanical properties and degradability without harmful gelling conditions are highly desired for regenerative medicine applications. Here we reported a method for preparing poly(ethylene glycol)-co-polycarbonate hydrogels through copper-free, strain-promoted azide-alkyne cycloaddition
A Versatile Monomer for Preparing Well-Defined Functional Polycarbonates and Poly(estercarbonates)
Xu J.; et al.
Macromolecules, 44, 2260-2267 (2011)
Strain-promoted copper-free "click" chemistry for 18F radiolabeling of bombesin.
Lachlan S Campbell-Verduyn et al.
Angewandte Chemie (International ed. in English), 50(47), 11117-11120 (2011-10-01)
View All Related Papers

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.

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.

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.

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service