70749-28-9

Basic information

• Product Name: 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose
• Synonyms: 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose
• CAS NO: 70749-28-9
• Molecular Weight: 347.322
• Mol File: 70749-28-9.mol
• Article Data: 51

Chemical Properties

• CAS DataBase Reference: 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose(70749-28-9)
• EPA Substance Registry System: 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose(70749-28-9)

Safety Data

• Hazardous Substances Data: 70749-28-9(Hazardous Substances Data)

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 107-18-6 allyl alcohol 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 63064-48-2 allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 76375-60-5 (3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 90-76-6 2-deoxy-2-amino glucose 
• 108-24-7 acetic anhydride 
• 51533-00-7 2-acetylamino-3,4,6-triacetyl-2-deoxy-α-D-glucopyranosyl bromide 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 170641-93-7 2-acetamido-1-O-butyroyl-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose 
• 10034-19-2 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrochloride 
• 65371-97-3 (E/Z)-prop-1-enyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 1233921-11-3 p-nitrophenoxycarbonyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 
• 147072-52-4 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yl ester 
• 79184-08-0 3,4,6-tri-O-acetyl-2-acetamido-1-O-[bis(benzyloxy)phophoryl]-2-deoxy-α-D-glucopyranose 
• 35695-00-2 4-methylphenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 

Relevant articles and documents

3'-KETOGLYCOSIDE COMPOUND FOR THE SLOW RELEASE OF A VOLATILE ALCOHOL

The present invention relates to a 3'-ketoglycoside compound defined by formula (I) and its use for controlled release of alcohols, in particular alcohols showing an insect repellent effect. It relates also to a process for preparing the 3'-ketoglycoside compound of formula (I). It further relates to a composition comprising a 3'- ketoglycoside compound of formula (I). It relates also to the use of a 3'-ketoglycoside compound of formula (I) for the controlled release of alcohols. It related also to a method of use of such composition.

A terpyridine zinc complex for selective detection of lipid pyrophosphates: A model system for monitoring bacterial O- And N-transglycosylations

To develop an effective method for probing O- and Nglycosyltransfer reactions that are accompanied by the release of undecaprenyl pyrophosphate, solanesyl pyrophosphate (SPP) is used as a surrogate to bind a terpyridine zinc complex (Tpy-Zn), forming a fluorescent [Tpy-Zn]-SPP complex (Kass 106,000 M-1 in EtOH-CHCl3) with 5.8 μM LOD in HEPES buffer (10 mM, pH 7.4) containing 10 mM CaCl2 and 0.08% decyl PEG, which is similar to the bioassay conditions for lipid II polymerization.

Protein S-Glyco-Modification through an Elimination-Addition Mechanism

Per-O-acetylated unnatural monosaccharides containing a bioorthogonal group have been widely used for metabolic glycan labeling (MGL) in live cells for two decades, but it is only recently that we discovered the existence of an artificial "S-glycosylation" between protein cysteines and per-O-acetylated sugars. While efforts are being made to avoid this nonspecific reaction in MGL, the reaction mechanism remains unknown. Here, we present a detailed mechanistic investigation, which unveils the "S-glycosylation" being an atypical glycosylation termed S-glyco-modification. In alkaline protein microenvironments, per-O-acetylated monosaccharides undergo base-promoted β-elimination to form thiol-reactive α,β-unsaturated aldehydes, which then react with cysteine residues via Michael addition. This S-glyco-modification produces 3-thiolated sugars in hemiacetal form, rather than typical glycosides. The elimination-addition mechanism guides us to develop 1,6-di-O-propionyl-N-azidoacetylgalactosamine (1,6-Pr2GalNAz) as an improved unnatural monosaccharide for MGL.