78962-39-7

Basic information

• Product Name: METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE
• Synonyms: METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE;methyl 6-O-A-D-mannopyranosyl-A-D-*mannopyranosid;Methyl6-O-(a-D-mannopyranosyl)-a-D-mannopyranoside;methyl 6-O-mannopyranosylmannopyranoside;Methyl 6-O-(α-D-Mannopyranosyl)-α-D-Mannopyranoside
• CAS NO: 78962-39-7
• Molecular Formula: C₁₃H₂₄O₁₁
• Molecular Weight: 356.32
• Product Categories: Carbohydrates & Derivatives
• Mol File: 78962-39-7.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE(78962-39-7)
• EPA Substance Registry System: METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE(78962-39-7)

Safety Data

• Hazardous Substances Data: 78962-39-7(Hazardous Substances Data)

Usage

Description

METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE is a complex carbohydrate derivative, specifically a disaccharide, consisting of two sugar units, alpha-D-mannopyranosyl and alpha-D-mannopyranoside, linked together. This molecule is of interest in the field of glycobiology due to its potential interactions with biological systems and its involvement in various biological processes.

Uses

Used in Pharmaceutical Research:
METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE is used as a research compound for studying the antiviral agent cyanovirin-N and its interactions with oligomannosides. This application is crucial for understanding the mechanisms of action and potential therapeutic uses of cyanovirin-N in treating viral infections.
Used in Glycomimetic Research:
METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE is used as a key component in the development of glycomimetics, specifically the C-glycosyl analog of the trisaccharide α-D-Man-(1 → 3)-[α-D-Man-(1 → 6)]-D-Man. This application is important for the design and synthesis of novel glycomimetic compounds with potential applications in various therapeutic areas, including the treatment of diseases related to carbohydrate recognition and binding.
Used in the Biochemical Industry:
In the biochemical industry, METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE is used as a starting material or intermediate in the synthesis of various complex carbohydrates and glycoconjugates. These synthesized products can be utilized in a wide range of applications, such as drug development, vaccine design, and the study of carbohydrate-mediated biological processes.
Used in the Food Industry:
METHYL 6-O-(ALPHA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE may also find applications in the food industry, particularly in the development of novel food additives or ingredients with enhanced nutritional or functional properties. The specific application would depend on the properties of the molecule and its compatibility with the food matrix.

Upstream product

• 477949-33-0 Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester 
• 29868-42-6 methyl 2,3-di-O-acetyl-α-D-glucopyranoside 
• 20231-39-4 methyl 2,3,4-tri-O-benzoyl-6-O-triphenylmethyl-α-D-glucopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 10357-27-4 4-nitrophenyl-α-D-mannopyranoside 
• 67-56-1 methanol 
• 76951-67-2 methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 210281-95-1 β-D-mannopyranosyl fluoride 
• 2713-54-4 α-D-mannopyranosyl fluoride 
• 80738-50-7 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose 
• 76679-49-7 methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 69895-14-3 methyl (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-β-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 

Relevant articles and documents

Binding of the Bacterial Adhesin FimH to Its Natural, Multivalent High-Mannose Type Glycan Targets

Multivalent carbohydrate-lectin interactions at host-pathogen interfaces play a crucial role in the establishment of infections. Although competitive antagonists that prevent pathogen adhesion are promising antimicrobial drugs, the molecular mechanisms underlying these complex adhesion processes are still poorly understood. Here, we characterize the interactions between the fimbrial adhesin FimH from uropathogenic Escherichia coli strains and its natural high-mannose type N-glycan binding epitopes on uroepithelial glycoproteins. Crystal structures and a detailed kinetic characterization of ligand-binding and dissociation revealed that the binding pocket of FimH evolved such that it recognizes the terminal α(1-2)-, α(1-3)-, and α(1-6)-linked mannosides of natural high-mannose type N-glycans with similar affinity. We demonstrate that the 2000-fold higher affinity of the domain-separated state of FimH compared to its domain-associated state is ligand-independent and consistent with a thermodynamic cycle in which ligand-binding shifts the association equilibrium between the FimH lectin and the FimH pilin domain. Moreover, we show that a single N-glycan can bind up to three molecules of FimH, albeit with negative cooperativity, so that a molar excess of accessible N-glycans over FimH on the cell surface favors monovalent FimH binding. Our data provide pivotal insights into the adhesion properties of uropathogenic Escherichia coli strains to their target receptors and a solid basis for the development of effective FimH antagonists.

Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrene-mediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the α1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the α1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the α1-2-analog displayed very similar binding compared to the O-linked structure.

A fluorous-assisted synthesis of oligosaccharides using a phenyl ether linker as a safety-catch linker

We report on the fluorous-assisted synthesis of oligosaccharides using a phenyl ether linker. The phenyl ether linker is stable under both acidic and basic conditions but can be cleaved under mildly acidic conditions after reduction to a vinyl ether. The utility of the method was demonstrated by the synthesis of a trisaccharide. A protected trisaccharide with a light-fluorous tag was directly prepared by one-pot glycosylation using three building blocks that contained a building block with a light-fluorous tag though a phenyl ether. A Birch reduction of the trisaccharide provided a fully deprotected trisaccharide with the fluorous tag attached through a vinyl ether, which was easily purified by solid-phase extraction. The tag was cleaved from the sugar portion by treatment with 3% TFA in MeOH.