913074-13-2

Usage

Uses

Used in Enzyme Research:
Propargyl a-D-Galactopyranoside is used as a substrate for studying the activity and specificity of glycosidases, such as α-D-galactosidase. This allows researchers to gain insights into the enzyme's catalytic mechanism and its potential applications in biotechnology and medicine.
Used in Transglycosylation Reactions:
Propargyl a-D-Galactopyranoside is used as a donor substrate in unique transglycosylation reactions catalyzed by extracellular α-D-galactosidase from Talaromyces flavus. This process enables the synthesis of novel oligosaccharides and glycoconjugates with potential applications in various industries, such as pharmaceuticals, food, and cosmetics.
Used in Chemical Synthesis:
The presence of the alkyne group in Propargyl a-D-Galactopyranoside allows for its use in click chemistry reactions, such as copper-catalyzed azide-alkyne cycloaddition (CuAAC). This enables the synthesis of various bioconjugates and functional materials with potential applications in drug delivery, imaging, and materials science.
Used in Analytical Chemistry:
Propargyl a-D-Galactopyranoside can be used as a derivatizing agent for the analysis of carbohydrates and related compounds. Its unique chemical properties allow for selective detection and quantification of target molecules in complex biological samples.

Upstream product

• 10257-28-0 D-Galactose 
• 107-19-7 propargyl alcohol 
• 28244-97-5 phenyl-1-thio-α-D-galactopyranoside 
• 28512-68-7 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 59-23-4 D-Galactose 
• 106-96-7 propargyl bromide 

Downstream Products

• 1195960-03-2 C₁₆H₁₈O₆ 
• 1422352-00-8 C₂₉H₃₃N₃O₁₁ 
• 1422351-99-2 C₂₉H₃₃N₃O₁₁ 

Relevant academic research and scientific papers

Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions

A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.

Novel Glycoconjugate of 8-Fluoro Norfloxacin Derivatives as Gentamicin-resistant Staphylococcus aureus Inhibitors: Synthesis and Molecular Modelling Studies

Antibiotic resistance has been the subject of interest in clinical practice due to high prevalence of antibiotic-resistant pathogenic organisms. In view of the prevalence of lesser resistance in antibiotics belonging to aminoglycoside class of compounds viz. Food and Drug Administration-approved gentamicin for the treatment of Staphylococcus infections, which also has instances of resistance in the clinical isolates of Staphylococcus aureus, a series of novel glycoconjugates of 8-fluoro norfloxacin analogues with high regio-selectivity by employing copper (I)-catalyzed 1, 3-dipolar cycloaddition of 1-O-propargyl monosaccharides has been synthesized and evaluated for the antibacterial activity against gentamicin resistance Staphylococcus aureus. Among these compounds, the compound 10g showed better antibacterial activity (MIC = 3.12 μg/ml) than gentamicin (Escherichia coli (12.5 μg/ml), Staphylococcus aureus (6.25 μg/ml) and Klebsiella pneumonia (6.25 μg/ml), including gentamicin resistant (>50 μg/ml) strain in vitro). The docking studies suggest DNA gyrase of Staphylococcus aureus as a probable target for the antibacterial action of compound 10g.

1,2-cis Alkyl glycosides: Straightforward glycosylation from unprotected 1-thioglycosyl donors

A 1,2-cis-alkyl glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors is reported. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1,2-cis-glycosides. In order to quickly develop optimum glycosylation conditions, an FIA (flow injection analysis)-ESI-TOF-MS method was developed that enabled rapid and quantitative evaluation of yield on small scale. This methodology, coupled with NMR spectroscopy, allowed for rapid evaluation of the overall reactions.

Supramolecular design of a bicomponent topochemical reaction between two non-identical molecules

We report the first design of a topochemical reaction between two non-identical reactants using a supramolecular chemistry approach. A coassembly of two sugar-based organogelators with complementary reacting motifs, viz. azides and alkynes, undergoes topochemical Huisgen reaction between them. The Royal Society of Chemistry 2013.

Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst

Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield.

Nucleoside triphosphate mimicry: A sugar triazolyl nucleoside as an ATP-competitive inhibitor of B. anthracis pantothenate kinase

The synthesis of a library of nucleoside triphoshate mimetics is described where the Mg2+ chelated triphosphate sidechain is replaced by an uncharged methylene-triazole linked monosaccharide sidechain. The compounds have been evaluated as inhib

Probing replacement of pyrophosphate via click chemistry; synthesis of UDP-sugar analogues as potential glycosyl transferase inhibitors

A series of potential UDP-sugar mimics were readily synthesised by copper(I) catalysed modified Huisgen cycloaddition of the corresponding α-propargyl glycosides with 5-azido uridine in aqueous solution. None of the compounds accessed displayed significant inhibitory activity at concentrations of up to 4.5 mM in an assay against bovine milk β-1,4-galactosyltransferase.