135608-52-5

Upstream product

• 70622-68-3 4-formylphenyl 3,4,6-tri-O-acetyl-2-(acetamido)-2-deoxy-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 135608-53-6 N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-hydroxymethyl-phenoxy)-tetrahydro-pyran-3-yl]-acetamide 

Relevant academic research and scientific papers

Development of specific fluorogenic substrates for human β-N-Acetyl-D-hexosaminidase a for cell-based assays

Inhibitors of human β-N-acetyl-D-hexosaminidase (hHEX) A and human O-GlcNAcase (hOGA) reportedly play roles in multiple diseases, suggesting their potential for pharmacological chaperone (PC) therapy of Sandhoff disease (SD) and Tay-Sachs disease (TSD), as lysosomal storage diseases, and Alzheimer's disease and progressive supranuclear palsy, respectively. In particular, hHEXA inhibitors as PCs have been shown to successfully enhance hHEXA levels, leading to the chronic form of SD and TSD. In the diagnosis of enzyme deficiencies in SD and TSD, artificial hHEXA substrates based on 4-methylumbelliferone as a fluorophore are available and generally used; however, they do not have sufficient performance to screen for potential inhibitors for a PC therapy from compound libraries. Further, there are currently few fluorogenic substrates for hHEXA suitable for such requirements and there are no substrates ideal for cell-based inhibitor screening. Here, we clarified the difference in enzyme active site structure between hHEXA and hOGA from their tertiary structures. To develop lysosome-localized hHEXA-specific fluorogenic substrates based on the difference in their active site structures, our developed quinone methide cleavage substrate design platform was applied for the molecular design of substrates. Thereafter, we synthesized via the shortest route and evaluated novel three-color fluorogenic substrates for hHEXA that exhibited excellent specificity and sensitivity in three human cell lines. The designed substrates represent the first-in-a class of new substrates that can be utilized to screen hHEXA inhibitors in adherent human cultured cells.

Glycosylnaphthalimide-containing fluorescent probe and application thereof

The invention discloses a glycosylnaphthalimide-containing fluorescent probe and application thereof in screening and cell imaging of a glycosidase inhibitor. The structure formula of the glycosylnaphthalimide-containing fluorescent probe is shown as form

Carbohydrate protein interactions. Syntheses of agglutination inhibitors of wheat germ agglutinin by phase transfer catalysis

Starting from chloride 1, a series of para-substituted aryl 2-acetamido-2-deoxy-β-D-glucopyranosides were prepared using phase transfer catalysis conditions with tetrabutylammonium hydrogen sulfate in 1 M sodium hydroxide and methylene chloride at room temperature.Zemplen de-O-acetylation afforded the unprotected glycosides.Optimization of reaction conditions was evaluated.Several functional group manipulations were effected to widen the number and nature of the para-substituents. Key words: phase transfer catalysis, aryl 2-acetamido-2-deoxy-β-D-glucopyranosides.