30628-06-9

Basic information

• Product Name: methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate
• CAS NO: 30628-06-9
• Molecular Weight: 376.317
• Mol File: 30628-06-9.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate(30628-06-9)
• EPA Substance Registry System: methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate(30628-06-9)

Safety Data

• Hazardous Substances Data: 30628-06-9(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 67-56-1 methanol 
• 487-44-5 D-(+)-glucuronic acid γ-lactone 
• 6556-12-3 D-glucuronic acid 
• 63-29-6 D-glucurono-6,3-lactone 
• 82228-14-6 methyl D-glucopyranuronate 
• 1190935-89-7 D-glucurono-6,3-lactone 

Downstream Products

• 39031-76-0 p-nitrophenyl-2,3,4-tri-O-acetyl-beta-D-galacturonic acid 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 
• 67776-38-9 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester 
• 14365-73-2 2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester 
• 1350467-71-8 methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate 
• 52173-67-8 methyl (2,4,6-trichlorophenyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 1350467-75-2 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-α-L-threo-hex-4-enopyranosid)uronate 
• 1350467-76-3 C₁₇H₁₅⁽²⁾H₂Cl₃O₈ 
• 1350467-77-4 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-5-C-bromo-4-{²H}-β-D-glucopyranosid)uronate 
• 1350467-78-5 methyl (2,4,6-trichlorophenyl 2,3-di-O-acetyl-4-deoxy-4-{(2)H}-α-L-threo-hex-4-enopyranosid)uronate 
• 1350467-79-6 methyl (phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosid)uronate 
• 1350467-81-0 phenyl 4-deoxy-5-C-methoxy-β-D-glucopyranosiduronic acid 
• 1350467-68-3 phenyl 4-deoxy-1-thio-α-L-threo-hex-4-enopyranosiduronic acid 
• 1350467-69-4 2,4,6-trichlorophenyl 4-deoxy-α-L-threo-hex-4-enopyranosiduronic acid 

Relevant articles and documents

Selective and Sensitive Sensing of Free Bilirubin in Human Serum Using Water-Soluble Polyfluorene as Fluorescent Probe

The adherence of serum protein on conjugated polymer is a major bottleneck in the application of the latter for selective sensing of small biomolecules in blood serum. In this report, we present new polyfluorenes with d-glucuronic acid appendage that is a nonreceptor for any serum protein, thereby providing a platform for selective sensing of free bilirubin in the clinically relevant range of 50 μmol/L in human blood serum. The appended d-glucuronic acid formed noncovalent interactions with bilirubin, which in conjunction with favorable spectral overlap between the polymers and bilirubin facilitated efficient FRET process in aqueous solutions. Addition of bilirubin resulted in the quenching of the polyfluorene emission with simultaneous appearance of bilirubin emission exhibiting visual emission color change from blue to light green. The polymer remained stable in serum even under severe basic conditions and exhibited high selectivity with visual sensitivity only toward free bilirubin in human serum in the presence of crucial interferences such as hemoglobin, proteins, biliverdin, glucose, cholesterol, and metal ions. Nanomolar sensing of bilirubin could also be demonstrated successfully using one of the d-glucuronic acid appended polymer (PF-Ph-GlcA), which could sense ～150 nm of bilirubin in human serum. The combined role of energy transfer and noncovalent interaction highlights the potential of the new polymer design for highly selective sensing activity in complex biofluids.

Potent and Prolonged Innate Immune Activation by Enzyme-Responsive Imidazoquinoline TLR7/8 Agonist Prodrug Vesicles

Synthetic immune-stimulatory drugs such as agonists of the Toll-like receptors (TLR) 7/8 are potent activators of antigen-presenting cells (APCs), however, they also induce severe side effects due to leakage from the site of injection into systemic circulation. Here, we report on the design and synthesis of an amphiphilic polymer-prodrug conjugate of an imidazoquinoline TLR7/8 agonist that in aqueous medium forms vesicular structures of 200 nm. The conjugate contains an endosomal enzyme-responsive linker enabling degradation of the vesicles and release of the TLR7/8 agonist in native form after endocytosis, which results in high in vitro TLR agonist activity. In a mouse model, locally administered vesicles provoke significantly more potent and long-lasting immune stimulation in terms of interferon expression at the injection site and in draining lymphoid tissue compared to a nonamphiphilic control and the native TLR agonist. Moreover, the vesicles induce robust activation of dendritic cells in the draining lymph node in vivo.

A combinatorial approach towards the synthesis of non-hydrolysable triazole-iduronic acid hybrid inhibitors of human α-l-iduronidase: Discovery of enzyme stabilizers for the potential treatment of MPSI

Preparation of substituent-diverse, triazole-iduronic acid hybrid molecules by click reaction of an azido iduronic acid derivative with randomly chosen alkynes is described. Library members were screened for their ability to inhibit α-l-iduronidase, and hit molecules and analogues were then investigated for their ability to stabilize rh-α-IDUA in a thermal denaturation study. This work resulted in the discovery of the first small molecules that can be used to stabilize exogenous rh-α-IDUA protein in vitro.