166516-67-2

Basic information

• Product Name: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside
• Synonyms: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside
• CAS NO: 166516-67-2
• Molecular Formula: C₁₂H₁₅N₃O₄S
• Molecular Weight: 297.3302
• Mol File: 166516-67-2.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside(166516-67-2)
• EPA Substance Registry System: Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside(166516-67-2)

Safety Data

• Hazardous Substances Data: 166516-67-2(Hazardous Substances Data)

Usage

Description

Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside is a chemical compound utilized in biochemical research as a probe for labeling and tracking glycoproteins. It features a phenyl group, an azido group, a thio group, and a glucopyranoside ring. Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside can be integrated with click chemistry to append fluorescent or other tags to glycoproteins, facilitating the examination of their behavior and function within biological systems. Additionally, as a thio sugar, it serves as a substrate for enzymes that participate in glycosylation. It is predominantly employed in laboratory settings for the investigation of glycoprotein structure and function.

Uses

Used in Biochemical Research:
Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside is used as a labeling probe for glycoproteins to enable the study of their structure and function in biological systems.
Used in Click Chemistry:
It is used as a component in click chemistry for attaching fluorescent or other tags to glycoproteins, which aids in the visualization and analysis of their behavior within biological contexts.
Used as a Substrate for Enzymes:
Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside is used as a substrate for enzymes involved in glycosylation, which is a crucial process in the biosynthesis of glycoproteins and other glycoconjugates.
Used in Laboratory Settings:
Phenyl2-azido-2-deoxy-1-thio-beta-D-glucopyranoside is primarily used in laboratory settings for the study of glycoprotein structure and function, contributing to the understanding of their roles in various biological processes and potential applications in medicine and biotechnology.

Upstream product

• 371123-22-7 phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 183875-22-1 phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside 
• 405290-57-5 phenyl 4,6-di-O-acetyl-2-azido-3-O-benzoyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 151662-55-4 phenyl 2,3:4,6-bis-O-isopropylidene-1-thio-β-D-mannopyranoside 
• 246875-61-6 phenyl 4,6-di-O-acetyl-1-thio-β-D-mannopyranoside 
• 246875-59-2 phenyl 4,6-di-O-acetyl-2,3-O-isopropylidne-1-thio-β-D-mannopyranoside 
• 405290-56-4 phenyl 4,6-di-O-acetyl-3-O-benzoyl-1-thio-β-D-mannopyranoside 
• 108-98-5 thiophenol 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 169557-87-3 phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside 
• 56644-75-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose 

Downstream Products

• 236115-65-4 2-azido-2-deoxy-3,4,6-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside 
• 801300-72-1 phenyl 2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 277756-87-3 phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 904690-67-1 phenyl 2-azido-2-deoxy-4,6-O-diphenylmethylidene-1-thio-β-D-glucopyranoside 
• 864862-22-6 Toluene-4-sulfonic acid (2R,3S,4R,5R,6S)-5-azido-3,4-dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 277756-84-0 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 663938-12-3 phenyl 2,6-diazido-2,6-dideoxy-1-thio-β-D-glucopyranoside 
• 864862-13-5 (1R,3R,4R,6R)-1-O-(2',6'-azido-2',6'-deoxy-3',4'-di-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol 
• 864862-12-4 (1S,3S,4S,6S)-1-O-(2',6'-azido-2',6'-deoxy-3',4'-di-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol 
• 664316-68-1 (2S,3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-phenylsulfanyl-tetrahydro-pyran 
• 904690-68-2 phenyl 2-azido-3-O-chloroacetyl-2-deoxy-4,6-O-diphenylmethylidene-1-thio-β-D-glucopyranoside 
• 904690-74-0 2-(trimethylsilyl)ethyl 4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 904690-75-1 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 

Relevant articles and documents

Stereoselectivity of Conformationally Restricted Glucosazide Donors

Glycosylations of 4,6-tethered glucosazide donors with a panel of model acceptors revealed the effect of acceptor nucleophilicity on the stereoselectivity of these donors. The differences in reactivity among the donors were evaluated in competitive glycosylation reactions, and their relative reactivities were found to be reflected in the stereoselectivity in glycosylations with a set of fluorinated alcohols as well as carbohydrate acceptors. We found that the 2-azido-2-deoxy moiety is more β-directing than its C-2-O-benzyl counterpart, as a consequence of increased destabilization of anomeric charge development by the electron-withdrawing azide. Additional disarming groups further decreased the α-selectivity of the studied donors, whereas substitution of the 4,6-benzylidene acetal with a 4,6-di-tert-butyl silylidene led to a slight increase in α-selectivity. The C-2-dinitropyridone group was also explored as an alternative for the nonparticipating azide group, but this protecting group significantly increased β-selectivity. All studied donors exhibited the same acceptor-dependent selectivity trend, and good α-selectivity could be obtained with the weakest acceptors and most reactive donors.

Agonistic and antagonistic properties of a Rhizobium sin-1 lipid A modified by an ether-linked lipid

LPS from Rhizobium sin-1 (R. sin-1) can antagonize the production of tumor necrosis factor alpha (TNF-α) by E. coli LPS in human monocytic cells. Therefore these compounds provide interesting leads for the development of therapeutics for the prevention or

Design, synthesis and evaluation of cytotoxic properties of bisamino glucosylated antitumor ether lipids against cancer cells and cancer stem cells

Glycosylated antitumor ether lipids (GAELs) are a class of amphiphilic antitumor agents that kill cancer cells by a non-apoptotic pathway. Previous studies have shown that 2-amino-2-deoxy-d-gluco-based GAELs such as α-GLN and β-GLN show greatly improved antitumor activity against epithelial cancer cells and stem cells. To further optimize the bioactivity, we prepared a series of diamino-d-gluco-based GAELs and their analogs, and screened them against a panel of human epithelial cancer cell lines and cancer stem cells. Most of the new GAEL analogs are more potent than chlorambucil, cisplatin and salinomycin. The most potent bisamine-based GAEL analogs 1, 2, 4 and 8 showed 2- to 3-fold enhanced cytotoxicity against various cancer cell lines when compared to β-GLN, indicating that the addition of a second amino group enhances the cytotoxic effect. The effect of the most active dicationic GAELs 1 and 4 on cancer stem cells isolated from breast (BT-474) and prostate (DU-145) cell lines revealed that the two GAELs inhibited the formation of tumor spheres and resulted in >95% loss of viability of the cancer stem cells at 5 μM. Activity of GAEL 1 against BT-474 cancer stem cells is superior to that of salinomycin.