824426-32-6

Basic information

• Product Name: Azidoacetic acid NHS ester
• Synonyms: Azidoacetic acid NHS ester;(2,5-dioxopyrrolidin-1-yl) 2-azidoacetate
• CAS NO: 824426-32-6
• Molecular Formula: C6H6N4O4
• Molecular Weight: 198.13624
• Mol File: 824426-32-6.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly)
• CAS DataBase Reference: Azidoacetic acid NHS ester(CAS DataBase Reference)
• NIST Chemistry Reference: Azidoacetic acid NHS ester(824426-32-6)
• EPA Substance Registry System: Azidoacetic acid NHS ester(824426-32-6)

Safety Data

• Hazardous Substances Data: 824426-32-6(Hazardous Substances Data)

Usage

Description

Azidoacetic acid NHS ester is a versatile chemical compound that contains both an azide group and an N-hydroxysuccinimide (NHS) ester. This unique structure allows it to participate in click chemistry reactions, specifically with alkyne or cyclooctyne groups, to form stable triazole linkages. Additionally, the NHS ester enables the compound to label primary amines, such as those found in proteins, amine-modified oligonucleotides, and other amine-containing molecules.

Uses

Used in Click Chemistry Applications:
Azidoacetic acid NHS ester is used as a simple azido-containing reagent for click chemistry, a set of reactions that are highly efficient, modular, and tolerant of a wide range of conditions. Azidoacetic acid NHS ester's azide group allows for chemoselective ligation with alkyne or cyclooctyne groups, resulting in the formation of a stable triazole linkage. This makes it a valuable tool for the synthesis of complex molecules and the study of molecular interactions.
Used in Bioconjugation:
In the field of bioconjugation, Azidoacetic acid NHS ester is used as a labeling agent for primary amines. The NHS ester reacts with primary amines to form stable amide bonds, allowing for the attachment of various functional groups to proteins, amine-modified oligonucleotides, and other amine-containing molecules. This is particularly useful in the development of bioconjugates for applications such as drug delivery, diagnostics, and therapeutics.
Used in Chemical Synthesis:
Azidoacetic acid NHS ester is also used in chemical synthesis as a building block for the creation of various azido-containing compounds. The azide group can be further modified or used as a handle for the attachment of other functional groups, making it a valuable intermediate in the synthesis of complex organic molecules.
Used in Materials Science:
In materials science, Azidoacetic acid NHS ester can be used to functionalize surfaces or create self-assembling materials. The azide group can be used to attach the compound to surfaces or other molecules, allowing for the creation of novel materials with unique properties.
Overall, Azidoacetic acid NHS ester is a multifaceted compound with a wide range of applications in various fields, including click chemistry, bioconjugation, chemical synthesis, and materials science. Its ability to form stable linkages and label primary amines makes it a valuable tool for researchers and scientists working with amine-containing molecules.

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 18523-48-3 2-azidoacetic acid 
• 105832-38-0 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 

Downstream Products

• 1534328-73-8 C₂₃H₃₁BN₆O₈ 

Relevant articles and documents

Click chemistry in the synthesis of the first glycoconjugates of bacteriochlorin series

A regioselective synthesis of glycoconjugates based on bacteriochlorophyll a and lactose derivatives has been carried out. The conjugation was achieved via 1,3-dipolar cycloaddition of bacteriochlorins containing a terminal triple bond and a lactose azide derivative. The conjugates obtained in this way had one or two disaccharide fragments attached to pyrrol A, the exocyclic imide ring of the tetrapyrrolyc macrocycle, or to both positions. Exhaustive NMR analysis by 1D and 2D NMR experiments (1H-1H COSY, TOCSY, ROESY, 1H-13C HSQC, HMBC, and 1H-15N HMBC) allowed us to determine the structures and configurations of the glycoconjugates obtained. A bioassay of the glycoconjugates using the Hep2 cell line showed that the highest efficiency was observed for the glycosylated bacteriopurpurinimide containing a lactose residue at pyrrole ring A.

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

The synthesis of a sulfate-modified dendritic peptide amphiphile and its self-assembly into one-dimensional rod-like architectures in aqueous medium is reported. The influence of the ionic strength on the supramolecular polymerization was probed via circular dichroism spectroscopy and cryogenic transmission electron microscopy. Physiological salt concentrations efficiently screen the charges of the dendritic building block equipped with eight sulfate groups and trigger the formation of rigid supramolecular polymers. Since multivalent sulfated supramolecular structures mimic naturally occurring L-selectin ligands, the corresponding affinity was evaluated using a competitive SPR binding assay and benchmarked to an ethylene glycol-decorated supramolecular polymer.

Design, synthesis and antibacterial activity evaluation of moxifloxacin-amide-1,2,3-triazole-isatin hybrids

In this work, a series of novel moxifloxacin-amide-1,2,3-triazole-isatin hybrids 7a-l were designed and synthesized. The in vitro antibacterial activity against a panel of clinically important Gram-positive and Gram-negative bacteria including drug-resistant pathogens was also evaluated. All hybrids showed considerable activity against the tested pathogens with MIC values of ≤0.03 to 128 μg/mL, and some of them such as hybrids 7e, 7g and 7j were comparable to or better than the parent moxifloxacin (MIC: ≤0.03–8 μg/mL). Moreover, hybrids 7e, 7g and 7j also demonstrated low cytotoxicity towards CHO cells. However, the in vivo pharmacokinetic profiles of these three hybrids were generally far inferior to the parent moxifloxacin. The structure-activity relationship and structure-cytotoxicity relationship were also studied and discussed which may help with the identification of new chemical entities as potent antibacterial agents.