882518-90-3

Basic information

• Product Name: Azido-PEG2-CH2CO2H
• Synonyms: Azido-PEG2-CH2CO2H;Azido-PEG2-CH2COOH;N3-PEG2-CH2COOH;2-[2-(2-Azidoethoxy)ethoxy]acetic acid
• CAS NO: 882518-90-3
• Molecular Formula: C₆H₁₁N₃O₄
• Molecular Weight: 189.16924
• Mol File: 882518-90-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Solubility: Soluble in Water
• CAS DataBase Reference: Azido-PEG2-CH2CO2H(CAS DataBase Reference)
• NIST Chemistry Reference: Azido-PEG2-CH2CO2H(882518-90-3)
• EPA Substance Registry System: Azido-PEG2-CH2CO2H(882518-90-3)

Safety Data

• Hazardous Substances Data: 882518-90-3(Hazardous Substances Data)

Usage

Description

Azido-PEG2-CH2CO2H is a water-soluble click chemistry reagent that features an azide group with a terminal carboxylic acid. This unique structure allows the azide group to engage in Click Chemistry reactions with alkyne, BCN, and DBCO, resulting in the formation of a stable triazole linkage. Additionally, the terminal carboxylic acid can react with primary amine groups in the presence of activators such as EDC or HATU, leading to the formation of a stable amide bond.

Uses

Used in Bioconjugation:
Azido-PEG2-CH2CO2H is used as a bioconjugation agent for the attachment of biomolecules to various surfaces or other molecules. The reason for its use in this application is its ability to form stable triazole linkages through Click Chemistry, which allows for the efficient and specific attachment of biomolecules.
Used in Drug Delivery Systems:
In the pharmaceutical industry, Azido-PEG2-CH2CO2H is used as a component in drug delivery systems for the targeted delivery of therapeutic agents. The stable amide bond formation with primary amine groups enables the conjugation of drugs to carriers or nanoparticles, improving the drug's solubility, stability, and targeted delivery to specific cells or tissues.
Used in Materials Science:
Azido-PEG2-CH2CO2H is utilized as a building block in the synthesis of functional materials, such as hydrogels, polymers, and surfaces with specific properties. The versatility of the azide group and terminal carboxylic acid allows for the creation of materials with tailored characteristics, such as biocompatibility, stimuli-responsiveness, and self-healing properties.
Used in Chemical Biology:
In the field of chemical biology, Azido-PEG2-CH2CO2H is employed as a tool for the study of biological processes and the development of probes. The ability to form stable linkages with a variety of molecules enables the investigation of protein-protein interactions, enzyme activity, and the development of molecular imaging agents.

Upstream product

• 86520-52-7 2-[2-(2-azidoethoxy)ethoxy]ethanol 
• 35718-08-2 propargyl chloroformate 
• 169396-89-8 tert-butyl N-(2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl)glycinate 

Downstream Products

• 945550-23-2 succinimidyl 8-azido-3,6-dioxaoctanoate 
• 134978-97-5 [2-(N-2-amino ethoxy)ethoxy] acetic acid 
• 1254054-66-4 C₁₉H₂₈N₄O₇ 

Relevant articles and documents

Template-directed synthesis of a small molecule-antisense conjugate targeting an mRNA structure

The targeting of structural features in mRNA with specificity remains a great chemical challenge. A hairpin structure near exon 10 in the pre-mRNA encoding the tau protein controls its splicing, and dementia-causing mutations that disrupt this structure increase exon 10 splicing. We previously reported the discovery of small molecules, mitoxantrone (MTX) and analogs, which bind to the tau RNA hairpin structure and the design of bipartite antisense oligonucleotides (ASOs) that simultaneously bind to the discontinuous sequences that flank this hairpin. Herein we report the synthesis of a bipartite ASO conjugated to MTX using the tau RNA hairpin and flanking sequences as a template. A set of six MTX analogs, each containing a linker-azide, and a set of ten bipartite ASOs, each containing a branched linker-alkyne, were synthesized and tested in combinatorial fashion for their ability to conjugate in the presence or absence of template RNA. A single template-dependent MTX-ASO conjugate was identified from among the 60 reaction mixtures, demonstrating that the MTX and ASO precursors could simultaneously bind the RNA template and allow proper positioning of azide and alkyne for 1,3-cycloaddition. While the MTX-ASO conjugate proved too cytotoxic for cell-based assays, the conjugate inhibited tau exon 10 splicing under cell-free conditions more effectively than MTX or bipartite ASO alone.

Ultra-Fast Synthesis of Multivalent Radical Nanoparticles by Ring-Opening Metathesis Polymerization-Induced Self-Assembly

We report the straightforward, time-efficient synthesis of radical core–shell nanoparticles (NPs) by polymerization-induced self-assembly. A nitroxide-containing hydrophilic macromolecular precursor was prepared by ring-opening metathesis copolymerization of norbornenyl derivatives of TEMPO and oligoethylene glycol and was chain-extended in situ with norbornene in ethanolic solution, leading to simultaneous amphiphilic block copolymer formation and self-assembly. Without any intermediate purification from the monomers to the block copolymers, radical NPs with tunable diameters ranging from 10 to 110 nm are obtained within minutes at room temperature. The high activity of the radical NPs as chemoselective and homogeneous, yet readily recyclable catalysts is demonstrated through oxidation of a variety of alcohols and recovery by simple centrifugation. Furthermore, the NPs show biocompatibility and antioxidant activity in vitro.

A novel heterotrifunctional peptide-based cross-linking reagent for facile access to bioconjugates. Applications to peptide fluorescent labelling and immobilisation

A convenient, versatile and straightforward synthesis of a novel heterotrifunctional peptide-based linker molecule is described. This generic bio-labelling reagent contains an amine-reactive N-hydroxysuccinimidyl carbamate moiety, an aldehyde/ketone-reactive aminooxy group and a thiol group with a propensity to form urea, oxime and thioether linkages respectively. The full chemical orthogonality between the free aminooxy and thiol functionalities was demonstrated through the preparation of a fluorescent reagent suitable for the selective staining of a carboxaldehyde-modified surface by means of oxime ligation. The absence of reactivity of these two functions toward the nucleophile-sensitive active carbamate was obtained by using temporary aminooxy- and thiol-protecting groups removable under mild conditions. The utility of the linker molecule to cross-link three different molecular partners has been illustrated by the preparation of fluorescent tripod-functionalised surfaces which may be useful in developing new peptide microarrays and related immunosensors.