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759902

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-acid

for Copper-free Click Chemistry

Synonym(s):

Polyethylene glycol, DBCO-PEG4-Acid

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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)

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Bioorthogonal Reaction Pairs Enable Simultaneous, Selective, Multi?Target Imaging
Karver MR, et al.
Angewandte Chemie (International Edition in English), 51(4), 920-922 (2012)
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)
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
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)
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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

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