78962-39-7

Usage

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

• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 82185-95-3 methyl 2,3-di-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 80738-50-7 1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose 
• 3254-15-7 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose 
• 40653-32-5 methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 68601-74-1 methyl 3,6-di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside 
• 6988-40-5 methyl 2,3-di-O-benzyl-α-D-mannopyranoside 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 79218-66-9 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl chloride 
• 80738-51-8 Acetic acid (2R,3R,4S,5S,6S)-2-acetoxymethyl-3,5-bis-benzyloxy-6-((2R,3S,4S,5S,6S)-3,5-bis-benzyloxy-4-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester 
• 80738-49-4 methyl 3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

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 structural investigation of a series of mannose-containing oligosaccharides using mass spectrometry

A series of compounds associated with naturally occurring and biologically relevant glycans consisting of α-mannosides were prepared and analyzed using collision-induced dissociation (CID), energy-resolved mass spectrometry (ERMS), and 1H nucle

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.

Completely β-selective glycosylation using 3,6- O-(o-xylylene)-bridged axial-rich glucosyl fluoride

A completely β-selective glycosylation that does not rely on neighboring group participation is described. The novelty of this work is the design of the glycosyl donor locked into the axial-rich form by the o-xylylene bridge between the 3-O and 6-O of d-glucopyranose. The synthesized 2,4-di-O-benzyl-3,6-O-(o-xylyene)glucopyranosyl fluoride could efficiently react with various alcohols in a SnCl2-AgB(C6F 5)4 catalytic system. The mechanism composed of the glycosylation and isomerization cycles was revealed through comparative experiments using acidic and basic molecular sieves. The achieved perfect stereocontrol is attributed to the synergy of the axial-rich conformation and convergent isomerization caused by HB(C6F5)4 generated in situ.

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.

Conformational flexibility and dynamics of two (1→6)-Linked disaccharides related to an oligosaccharide epitope expressed on malignant tumour cells

The conformational flexibility and dynamics of two (1→6)-linked disaccharides that are related to the action of the glycosyl transferase GnT-V have been investigated. NMR NOE and T-ROE spectroscopy experiments, conformation-dependent coupling constants an

How the arming participating moieties can broaden the scope of chemoselective oligosaccharide synthesis by allowing the inverse armed-disarmed approach

(Chemical Equation Presented) A new method for stereocontrolled glycosylation and chemoselective oligosaccharide synthesis has been developed. It has been determined that complete 1,2-trans selectivity can be achieved with the use of a 2-O-picolyl moiety,

Development of an arming participating group for stereoselective glycosylation and chemoselective oligosaccharide synthesis

(Chemical Equation Presented) Armed and dangerous: A new armed-disarmed glycosylation strategy (see picture) allows chemoselective introduction of a 1,2-trans glycosidic linkage prior to other linkages through the use of a 2-O-picolyl moiety. This neighbo

Removal of benzyl protecting groups from controlled pore glass linked sugars

Removal of benzyl protecting groups from controlled pore glass bound monosaccharides can be performed with the NaBrO3/Na2S2O4 system in ethyl acetate/water.

Transglycosylation reactions with a crude culture filtrate from Thermoascus aurantiacus

Some characteristics of regioselectivity and acceptor tolerance in transglycosylation reactions, catalysed by a crude culture filtrate from Thermoascus aurantiacus, were examined by employing methanol and monosaccharides as acceptors. When β-D-mannopyranosyl fluoride was employed as the donor, the anomeric configuration of the newly formed bond was found to depend on the structure of the acceptor used. Copyright (C) 2000 Elsevier Science Ltd.