165331-08-8

Basic information

• Product Name: 2-Azidoethyl beta-D-Glucopyranoside
• Synonyms: 2-Azidoethyl beta-D-Glucopyranoside;2-Azidoethyl β-D-Glucopyranoside;2-Azidoethyl &beta
• CAS NO: 165331-08-8
• Molecular Formula: C₈H₁₅N₃O₆
• Molecular Weight: 249.2212
• Mol File: 165331-08-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: <0°C
• CAS DataBase Reference: 2-Azidoethyl beta-D-Glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azidoethyl beta-D-Glucopyranoside(165331-08-8)
• EPA Substance Registry System: 2-Azidoethyl beta-D-Glucopyranoside(165331-08-8)

Safety Data

• Hazardous Substances Data: 165331-08-8(Hazardous Substances Data)

Usage

General Description

2-Azidoethyl beta-D-Glucopyranoside is a chemical compound that consists of a glucopyranoside molecule linked to an azidoethyl group. It is commonly used as a precursor in chemical reactions that involve the modification of carbohydrates. The azidoethyl group can undergo reactions such as click chemistry, which allows for the attachment of other molecules or compounds to the glucopyranoside. This chemical compound is often used in the synthesis of glycoconjugates, which are important in the fields of biochemistry, medicine, and materials science. Additionally, 2-Azidoethyl beta-D-Glucopyranoside has potential applications in the development of new pharmaceuticals and biomaterials due to its ability to be modified and conjugated with other molecules.

InChI:InChI=1/C8H15N3O6/c9-11-10-1-2-16-8-7(15)6(14)5(13)4(3-12)17-8/h4-8,12-15H,1-3H2/t4-,5+,6-,7-,8+/m0/s1

Upstream product

• 230286-11-0 2-azidoethyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 

Downstream Products

• 189758-87-0 Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 220689-77-0 2-aminoethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 1443234-37-4 2-azidoethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 1335002-97-5 2'-azidoethyl-6-O-trityl-2,3,4-tri-O-acetyl-β-D-glucopyranoside 
• 1383446-35-2 2'-azidoethyl 2,3-di-O-benzyl-6-O-p-methoxybenzyl-β-D-glucopyranoside 
• 1383446-36-3 C₃₈H₄₃NO₉ 
• 1386972-65-1 2'-(9H-fluoren-9-yl)methoxycarbonylaminoethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 1386972-62-8 2'-azidoethyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant articles and documents

Measuring Bacterial Glycosyl Hydrolase Activity with a Soluble Capture Probe by Mass Spectrometry

A solution-phase enzymatic assay has been developed to track bacterial glycosyl hydrolase activity by surface-assisted MALDI-TOF mass spectrometry. Lactose was equipped with an azide-functionalized linker and was supplemented to bacterial cultures as an artificial substrate for bacterial β-galactosidase enzyme. The azide linked glycoside probe was then covalently captured on an alkyne-functionalized indium tin oxide sample plate via a bio-orthogonal copper-catalyzed azide alkyne cycloaddition (CuAAC). The noncovalent immobilization of the alkyne capture tag via hydrophobic interactions on the ITO-sample plate allowed the analysis of the probe conjugate by surface-based mass spectrometry. The ratio of digested to nondigested lactose probe was then employed as a measure for bacterial hydrolase activity, which correlated well with bacterial growth measured by optical density. In addition, we established in a proof of concept experiment that the setup was well suited to identify antibiotic susceptibility of bacterial strains with a performance comparable to current state-of-the-art methods. While the proof of concept version is limited to the identification of a single enzyme activity, we envisage that the use of multiple substrate probes in a multiplexed version will allow the quantification of various glycosyl hydrolase activities with clinical relevance in a single experiment.