5155-54-4

Basic information

• Product Name: alpha-D-Galactopyranosiduronic acid, methyl, methyl ester
• Synonyms: alpha-D-Galactopyranosiduronic acid, methyl, methyl ester;Methyl α-D-galactopyranosiduronic acid methyl ester;1-O-Methyl-β-D-glucuronide Methyl Ester
• CAS NO: 5155-54-4
• Molecular Formula: C₈H₁₄O₇
• Molecular Weight: 222.19
• Mol File: 5155-54-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Water
• CAS DataBase Reference: alpha-D-Galactopyranosiduronic acid, methyl, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-D-Galactopyranosiduronic acid, methyl, methyl ester(5155-54-4)
• EPA Substance Registry System: alpha-D-Galactopyranosiduronic acid, methyl, methyl ester(5155-54-4)

Safety Data

• Hazardous Substances Data: 5155-54-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
alpha-D-Galactopyranosiduronic acid, methyl, methyl ester is used as a key intermediate in the synthesis of pharmaceutical compounds for various therapeutic applications. Its unique structural properties allow for the development of novel drugs with potential benefits in treating different medical conditions.
Used in Drug Delivery Systems:
In the field of drug delivery, alpha-D-Galactopyranosiduronic acid, methyl, methyl ester can be utilized as a component in the design and development of targeted drug delivery systems. Its ability to interact with specific biological targets can enhance the specificity and efficacy of drug delivery, potentially improving patient outcomes.
Used in Research and Development:
This carbohydrate derivative is also used in research and development for the study of carbohydrate chemistry, biochemistry, and the development of new pharmaceutical compounds. Its unique properties make it a valuable tool for understanding the role of carbohydrates in biological processes and the development of new therapeutic strategies.
Used in the Cosmetics Industry:
In the cosmetics industry, alpha-D-Galactopyranosiduronic acid, methyl, methyl ester may be used as an ingredient in the formulation of skincare and beauty products. Its properties could potentially contribute to the development of products with enhanced moisturizing, anti-aging, or skin-protective effects.
Used in the Food Industry:
In the food industry, this carbohydrate derivative may find applications in the development of novel additives, preservatives, or flavor enhancers. Its unique properties could potentially improve the taste, texture, or shelf life of various food products.

Upstream product

• 67-56-1 methanol 
• 685-73-4 D-galacturonic acid 
• 489-91-8 D-galacturonic acid 
• 83075-41-6 methyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid)uronate 
• 77-76-9 2,2-dimethoxy-propane 
• 5155-53-3 methyl α-D-galactopyranosiduronic acid 
• 643-33-4 D-galacturonic acid 
• 6294-16-2 D-galacturonic acid 
• 18311-26-7 methyl 6-O-triphenylmethyl-α-D-galactopyranoside 
• 164323-13-1 (2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid 
• 4356-80-3 methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 

Downstream Products

• 51432-81-6 O¹,O²-dimethyl-α-D-galactopyranuronic acid amide 
• 25253-47-8 methyl (methyl 3,4-O-isopropylidene-α-D-galactopyranoside)uronate 
• 93527-89-0 benzyl 1-O-acetyl 2,3,4-tri-O-benzyl-α-D-galactopyranuronate 
• 93527-88-9 benzyl (methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside)uronate 
• 93527-90-3 benzyl (2,3,4-tri-O-benzyl-α-D-galactopyranosyl bromide)uronate 
• 93414-81-4 methyl 2-acetamido-4-azido-3-O-(benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosyluronate)-2,4,6-trideoxy-α-D-galactopyranoside 
• 52678-33-8 1-(methyl ester of 2,3,4-tri-O-benzoyl-β-D-galactopyranuronosyl)uracil 
• 55610-61-2 methyl ester of methyl 2,3,4-tri-O-benzoyl-α-D-galactopyranuronoside 
• 35785-35-4 methyl 2,3,4-tri-O-acetyl-α-D-galactopyranosiduronic acid methyl ester 

Relevant articles and documents

Glycoside cleavage by a new mechanism in unsaturated glucuronyl hydrolases

Unsaturated glucuronyl hydrolases (UGLs) from GH family 88 of the CAZy classification system cleave a terminal unsaturated sugar from the oligosaccharide products released by extracellular bacterial polysaccharide lyases. This pathway, which is involved in extracellular bacterial infection, has no equivalent in mammals. A novel mechanism for UGL has previously been proposed in which the enzyme catalyzes hydration of a vinyl ether group in the substrate, with subsequent rearrangements resulting in glycosidic bond cleavage. However, clear evidence for this mechanism has been lacking. In this study, analysis of the products of UGL-catalyzed reactions in water, deuterium oxide, and dilute methanol in water, in conjunction with the demonstration that UGL rapidly cleaves thioglycosides and glycosides of inverted anomeric configuration (substrates that are resistant to hydrolysis by classical glycosidases), provides strong support for this new mechanism. A hydration-initiated process is further supported by the observed UGL-catalyzed hydration of a C-glycoside substrate analogue. Finally, the observation of a small β-secondary kinetic isotope effect suggests a transition state with oxocarbenium ion character, in which the hydrogen at carbon 4 adopts an axial geometry. Taken together, these observations validate the novel vinyl ether hydration mechanism and are inconsistent with either inverting or retaining direct hydrolase mechanisms at carbon 1.

Synthesis of apiose-containing oligosaccharide fragments of the plant cell wall: Fragments of rhamnogalacturonan-II side chains A and B, and apiogalacturonan

Fragments of pectic polysaccharides rhamnogalacturonan-II (RG-II) and apiogalacturonan were synthesised using p-tolylthio apiofuranoside derivatives as key building blocks. Apiofuranose thioglycosides can be conveniently prepared by cyclization of the cor

Electroorganic synthesis 66: Selective anodic oxidation of carbohydrates mediated by TEMPO

The carbohydrates 4-15 are anodically oxidized with 2,2,6,6- tetramethylpiperidin-1-oxyl (TEMPO) as mediator. Selective and complete reaction at the primary hydroxyl groups affords the corresponding carboxylic acids 16-32 in moderate to excellent yield. Methyl α-D-glucopyranoside is converted in 98% yield to the uronic acid 16. Cyclic voltammetry shows that the oxydation is base-catalyzed and the oxidation of the hydroxy group with TEMPO+ (2) is rate determining.

SELECTIVE DEGRADATION OF THE GLYCOSYLURONIC ACID RESIDUES OF COMPLEX CARBOHYDRATES BY LITHIUM DISSOLVED IN ETHYLENEDIAMINE

Lithium metal dissolved in ethylenediamine had been demonstrated to cleave a 3-linked glycosyluronic acid-containing polysaccharide .The present study with model compounds has established that, by lithium treatment, carbohydrates are cleaved at the sites of the glycosyluronic acid residues, regerdless of the point at which other glycosyl residues are attached to the glycosyluronic acid residue.Treatment of carbohydrates with lithium metal dissolved in ethylenediamine also results in cleavage of methyl glycosides, reduction of aldoses, and cleavage of methyl ethers and pyruvic acetals of glycosyl residues.Model compounds were used to demonstrate that oligosaccharides containing only neutral glycosyl residues are largely stable to the reaction conditions (except for the reduction of the glycose residue of each oligosaccharide).Thus, a general procedure for the selective cleavage of underivatized carbohydrates at the glycosyluronic acid residues is described.

METHANOLYSIS STUDIES OF CARBOHYDRATES, USING H.P.L.C.

An h.p.l.c. system that separates carbohydrates as their methyl glycosides has been used to study the products obtained on treatment of various carbohydrates with methanolic hydrogen chloride.Results are presented for the monosaccharide composition of several polysaccharides, lactone and ester formation during the treatment of D-glucuronic acid, and relative rates of glycosidation vs. esterification during the treatment of D-galacturonic acid.

SYNTHESIS OF METHYL DERIVATIVES OF URONIC ACIDS. I. SYNTHESIS OF METHYL (METHYL Α-D-GALACTOPYRANOSID)URONATE AND ITS 2-, 3-, AND 4-O-METHYL ETHERS

Alternative unidirectional methods for synthesizing methyl (methyl α-D-galactopyranosid)uronate and its mono-O-methyl ethers by the oxidation (with CrO3-H2SO4-acetone) of the corresponding methyl O-benzyl-O-methyl-α-D-galactopyranosides having unsubstituted 6-OH groups to the corresponding methyl O-benzyl-O-methyl-α-D-galactouronic acids followed by esterification with CH2N2 and the catalytic hydrogenolysis of the benzyl groups are proposed.

PROTON AND CARBON-13 NUCLEAR MAGNETIC RESONANCE STUDIES ON METHYL (METHYL D-GALACTOSID)URONATES AND THEIR PER-O-ACETYL DERIVATIVES

The 1H- and 13C-n.m.r. spectra of the anomeric methyl (methyl D-galactosid)uronates, as well as the 1H-n.m.r. spectra of their acetyl derivatives, were analyzed.The spectra of the unacetylated D-galactopyranosiduronates showed good correlation with those of the corresponding anomeric D-galactopyranuronic acids and their methyl esters, and with those of the anomeric methyl D-galactopyranosides.From the values of the chemical shifts and coupling constants, it was concluded that the anomeric methyl (methyl D-galactopyranosid)uronates and their corrasponding peracetates are in the 4C1(D) conformation.The chemical shifts in the 13C-n.m.r. spectra show good correlation with those of the methyl D-galactosides.The signals of the furanose derivatives appear at fields lower than those of the corresponding pyranose compounds.