476330-50-4

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 476330-47-9 [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid benzyl ester 
• 476330-54-8 [4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acetic acid 
• 27727-37-3 benzyl p-hydroxyphenylacetate 
• 476330-48-0 [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-acetic acid 2-cyanoethyl ester 
• 156-38-7 4-hydroxyphenylacetate 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 880490-76-6 (4-hydroxy-phenyl)-acetic acid 2-cyano-ethyl ester 
• 476330-49-1 [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-bromoacetic acid 2-cyanoethyl ester 

Downstream Products

• 476330-51-5 [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetic acid 2-cyanoethyl ester 
• 476330-53-7 N-[4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine 
• 476330-52-6 triethylammonium [4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-fluoroacetate 

Relevant academic research and scientific papers

Facile synthesis toward the construction of an activity probe library for glycosidases

Chemical probes that selectively label the glycoside hydrolase (GH) subfamilies have proven to be a powerful tool in GH-related research. We have previously demonstrated the design and synthesis of an activity probe for β-glucosidase adopting a cassette-like design in a model study. Herein we report an improved synthetic route using (4-hydroxyphenyl)acetic acid 2-cyanoethyl ester as the precursor for the latent trapping device. Parallel syntheses were performed for the preparation of a library based on the structure of a key intermediate. The recognition head of this library covers a series of six sugars, including α- and β-D-Glc, α- and β-D-Gal, α-D-Man, and α-L-Fuc. Each member in this versatile intermediate library could serve as the building block in constructing an activity probe for GHs. As demonstrated in this study, three probes that have the 1,2-cis configuration were thus prepared for the first time to target α-D-glucosidase, α-D-galactosidase, and α-L-fucosidase, respectively.

Design and synthesis of activity probes for glycosidases

(graph presented) A new synthetic route was developed for the preparation of activity probe 1 for β-glucosidase in this study. The key glycosidation step begins with benzyl p-hydroxyphenylacetate. Benzylic functionalization for the construction of the tra