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759902

Dibenzocyclooctyne-PEG4-acid

Name: Dibenzocyclooctyne-PEG4-acid
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

329766822

UNSPSC Code:

12352106

MDL number:

MFCD22380749

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Properties

Quality Level

100

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

Description

Application

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

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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.

无铜点击化学

无铜点击化学是点击化学的一种替代方法，可在较低的活化屏障下进行，且没有细胞毒性过渡金属催化剂。

Bioorthogonal Reaction Pairs Enable Simultaneous, Selective, Multi?Target Imaging

Karver MR, et al.

Angewandte Chemie (International Edition in English), 51(4), 920-922 (2012)

[18F]azadibenzocyclooctyne ([18F]ADIBO): a biocompatible radioactive labeling synthon for peptides using catalyst free [3+2] cycloaddition.

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

Cytocompatible poly(ethylene glycol)-co-polycarbonate hydrogels cross-linked by copper-free, strain-promoted click chemistry.

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

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Global Trade Item Number

SKU	GTIN
759902-50MG	04061833230435
759902-5MG	04061833230442