478529-35-0

Usage

Uses

Used in Chemical Synthesis:
TRI-O-ACETYL-D-[1-13C]GLUCAL is used as a key intermediate in the synthesis of various complex carbohydrates and their derivatives. Its unique 13C labeling enables researchers to monitor the incorporation and metabolic fate of these synthesized compounds in biological systems.
Used in Pharmaceutical Research:
TRI-O-ACETYL-D-[1-13C]GLUCAL serves as a valuable tool in the development of new pharmaceutical agents targeting carbohydrate-related diseases. Its 13C labeling allows for the investigation of drug-target interactions and the elucidation of the mechanisms of action of potential therapeutic agents.
Used in Metabolic Studies:
In the field of metabolic research, TRI-O-ACETYL-D-[1-13C]GLUCAL is employed as a tracer compound to study the metabolic pathways and enzyme activities involved in carbohydrate metabolism. The 13C isotope provides a means to differentiate the labeled compound from endogenous metabolites, facilitating the analysis of metabolic fluxes and enzyme kinetics.
Used in Analytical Techniques:
TRI-O-ACETYL-D-[1-13C]GLUCAL is utilized in various analytical techniques, such as mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy, to enhance the detection and characterization of carbohydrates and their derivatives. The 13C labeling improves the spectral resolution and sensitivity of these techniques, allowing for more accurate and reliable measurements.
Used in Material Science:
In the field of material science, TRI-O-ACETYL-D-[1-13C]GLUCAL is employed in the development of carbohydrate-based materials with tailored properties. The 13C labeling can be used to study the structure-property relationships and the self-assembly behavior of these materials, leading to the design of advanced materials for various applications.
Used in Food Industry:
TRI-O-ACETYL-D-[1-13C]GLUCAL is used in the food industry for the development of novel food products with improved nutritional profiles and health benefits. The 13C labeling can be employed to study the digestion, absorption, and metabolic effects of these products in the human body, guiding the optimization of their formulation and processing.
Used in Environmental Science:
In environmental science, TRI-O-ACETYL-D-[1-13C]GLUCAL is utilized for the study of the fate and transport of carbohydrates in the environment. The 13C labeling allows for the tracking of these compounds in various environmental matrices, such as soil, water, and air, providing insights into their degradation, transformation, and ecological impacts.

Upstream product

• 299172-50-2 [glucose-U-(13)C6]-1,2,3,4,6-penta-O-acetyl-α/β-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 40010-55-7 ¹³C-C₁-glucopyranose 

Relevant academic research and scientific papers

Structure of the Complex between a Heparan Sulfate Octasaccharide and Mycobacterial Heparin-Binding Hemagglutinin

Heparin-binding hemagglutinin (HBHA) is a 199 amino acid virulence factor at the envelope of Mycobacterium tuberculosis that contributes to latent tuberculosis. The binding of HBHA to respiratory epithelial cells, which leads to extrapulmonary dissemination of the pathogen, is mediated by cell-surface heparan sulfate (HS). We report the structural characterization of the HBHA/HS complex by NMR spectroscopy. To develop a model for the molecular recognition, the first chemically synthesized uniformly 13C- and 15N-labeled HS octasaccharide and a uniformly 13C- and 15N-labeled form of HBHA were prepared. Residues 180–195 at the C-terminal region of HBHA show large chemical shift perturbation upon association with the octasaccharide. Molecular dynamics simulations conforming to the multidimensional NMR data revealed key electrostatic and even hydrophobic interactions between the binding partners that may aid in the development of agents targeting the binding event.

Solid-phase synthesis and 1H and 13C high-resolution magic angle spinning NMR of 13C-labeled resin-bound saccharides

We show how high-resolution magic angle-spinning NMR spectroscopy can be used to characterize 13C-labeled saccharides that have been prepared using solid-phase synthesis techniques while they are still bound to a solid-support resin. With the u

C2-hydroxyglycosylation with glycal donors. Probing the mechanism of sulfonium-mediated oxygen transfer to glycal enol ethers

The C2-hydroxyglycosylation reaction employing the reagent combination of a diaryl sulfoxide and triflic anhydride offers a novel method for glycal assembly whereby a hydroxyl functionality is stereoselectively installed at the C2-position of a glycal donor with concomitant glycosylation of a nucleophilic acceptor. Mechanistic investigations into this reaction revealed a novel process for sulfonium-mediated oxidation of glycal enol ethers in which the sulfoxide oxygen atom is stereoselectively transferred to the C2-position of the glycal. 18O-labeling studies revealed that the S-to-C2 oxygen-transfer process involves initial formation of a C1-O linkage followed by O-migration to C2, leading to the generation of an intermediate glycosyl 1,2-anhydropyranoside that serves as an in situ glycosylating agent. These findings are consistent with the initial formation of a C2-sulfonium-C1-oxosulfonium pyranosyl species upon activation of the glycal donor with Aryl2SO·Tf2O.