20590-45-8

Basic information

• Product Name: 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE
• Synonyms: 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE;2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosylisothiocyanate
• CAS NO: 20590-45-8
• Molecular Formula: C₁₅H₂₀N₂O₈S
• Molecular Weight: 388.3929
• Mol File: 20590-45-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE(20590-45-8)
• EPA Substance Registry System: 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSYL ISOTHIOCYANATE(20590-45-8)

Safety Data

• Hazardous Substances Data: 20590-45-8(Hazardous Substances Data)

Usage

General Description

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl isothiocyanate is a chemical compound that is commonly used in biochemical research. It is a derivative of glucopyranosyl isothiocyanate and is known for its ability to label and modify proteins and peptides. The compound contains acetyl and acetamido groups, which contribute to its reactivity and labeling properties. It is often utilized as a reagent in the synthesis of bioconjugates and fluorescently labeled proteins, as well as in the study of protein-protein interactions and protein localization within cells. Additionally, it has potential applications in the development of new drugs and biomaterials.

Upstream product

• 333-20-0 potassium thioacyanate 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 1701-93-5 silver thiocyanate 
• 3068-34-6 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride 
• 4515-24-6 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 6205-69-2 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide 
• 51533-00-7 2-acetylamino-3,4,6-triacetyl-2-deoxy-α-D-glucopyranosyl bromide 

Relevant articles and documents

Total synthesis of TRADD death domain with arginine N-GlcNAcylation by hydrazide-based native chemical ligation

TNFR1-associated death domain protein (TRADD) with arginine N-GlcNAcylation is a novel and structurally unique posttranslational modification (PTM) glycoprotein that blocks the formation of death-inducing signaling complex (DISC), orchestrating host nuclear factor κB (NF-κB) signaling in entero-pathogenic Escherichia coli (EPEC)-infected cells. This particular glycosylated modification plays an extremely vital role for the effective colonization and pathogenesis of pathogens in the gut. Herein we describe the total synthesis of TRADD death domain (residues 195–312) with arginine235 N-GlcNAcylation (Arg-GlcNAc TRADD (195–312)). Two longish peptidyl fragments of the wild-type primary sequence were obtained by robust, microwave-assisted, highly efficient, solid-phase peptide synthesis (SPPS), the N-GlcNAcylated sector was built by total synthesis and attached specifically to resin-bound peptide with an unprotected ornithine residue via silver-promoted on-resin guanidinylation, Arg-GlcNAc TRADD (195–312) was constructed by hydrazide-based native chemical ligation (NCL). The facile synthetic strategy is expected to be generally applicable for the rapid synthesis of other proteins with Arg-GlcNAc modification and to pave the way for the related chemically biological study.

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives

Eight glycosyl benzoxazole derivatives are synthesized by nucleophilic addition reactions of glycosyl isothiocyanate with o-aminophenol in tetrahydrofuran. The reaction conditions are optimized, and good yields (86%–94%) were obtained. The structures of all new products are confirmed by infrared, 1H nuclear magnetic resonance, and high-resolution mass spectrometry (electrospray ionization). In addition, the in vitro cholinesterase inhibitory activities of these new compounds are tested by Ellman’s method.