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764248

Sigma-Aldrich

Amino-PEG4-alkyne

Synonym(s):

3,6,9,12-Tetraoxapentadec-14-yn-1-amine, Acetylene-PEG4-amine, H2N-PEG4-propyne, Triethylene glycol 2-aminoethyl propargyl ether

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About This Item

Empirical Formula (Hill Notation):
C11H21NO4
CAS Number:
1013921-36-2
Molecular Weight:
231.29
MDL number:
MFCD22380736
UNSPSC Code:
12352106
PubChem Substance ID:
329767109
NACRES:
NA.22

form

liquid

reaction suitability

reaction type: click chemistry
reagent type: cross-linking reagent

functional group

alkyne
amine

storage temp.

−20°C

SMILES string

NCCOCCOCCOCCOCC#C

InChI

1S/C11H21NO4/c1-2-4-13-6-8-15-10-11-16-9-7-14-5-3-12/h1H,3-12H2

InChI key

QDLPAHLHHBCWOW-UHFFFAOYSA-N

Application

Heterobifunctional linker enabling the connection of an azide containing compound or biomolecule to one with a carboxylic acid. The amine group can be linked to a carboxylic acid through standard coupling procedures (EDC, product #39391, etc...) and the terminal alkyne will react with azides via copper-catalyzed 1,3-dipolar cycloaddition click chemistry. The hydrophilic PEG spacer adds to the water solubility of this reagent, allowing for easy modification of carboxylic acid containing biomolecules such as antibodies, proteins and peptides with the terminal alkyne. The PEG spacer also reduces aggregation of modified proteins stored in solution by adding hydrophilic character.
Amino-PEG4-alkyne may be used to synthesize alkynyl-functionalized iron oxide nanoparticles (IONPs) for preparing glycopolymer-based iron oxide nanoparticles (GIONs) for potential bioscience applications.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Strain-promoted azide?alkyne cycloaddition for protein?protein coupling in the formation of a bis-hemoglobin as a copper-free oxygen carrier
Singh S, et al.
Organic & Biomolecular Chemistry (2016)
Facile fabrication of glycopolymer-based iron oxide nanoparticles and their applications in the carbohydrate?lectin interaction and targeted cell imaging.
Shao C, et al.
Polym. Chem., 7(6), 1337-1344 (2016)

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