Category: 2595/7/5

Timmer, Brian J. J. published the artcileAcid-Assisted Direct Olefin Metathesis of Unprotected Carbohydrates in Water, Product Details of C9H16O6, the main research area is disaccharide glycoside chelation galactopyranoside mannoside preparation olefin metathesis minimization; carbene ligands; carbohydrates; homogeneous catalysis; olefin metathesis; synthetic methods.

The ability to use unprotected carbohydrates in olefin metathesis reactions in aqueous media is demonstrated. By using water-soluble, amine-functionalized Hoveyda-Grubbs catalysts under mildly acidic aqueous conditions, the self-metathesis of unprotected alkene-functionalized α-D-manno- and α-D-galactopyranosides could be achieved through minimization of non-productive chelation and isomerization. Cross-metathesis with allyl alc. could also be achieved with reasonable selectivity. The presence of small quantities (2.5 vol %) of acetic acid increased the formation of the self-metathesis product while significantly reducing the alkene isomerization process. These results demonstrate the potential of directly using unprotected carbohydrate structures in olefin metathesis reactions under mild conditions compatible with biol. systems, and thereby enabling their use in, for example, drug discovery and protein derivatization.

Chemistry – A European Journal published new progress about Chelation. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, Product Details of C9H16O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Cai, Zhongyu published the artcileResponsive Photonic Crystal Carbohydrate Hydrogel Sensor Materials for Selective and Sensitive Lectin Protein Detection, HPLC of Formula: 2595-07-5, the main research area is photonic crystal carbohydrate hydrogel sensor detection lectin; biosensors; carbohydrate hydrogels; copolymerization; lectin proteins detection; photonic crystals.

Lectin proteins, such as the highly toxic lectin protein, ricin, and the immunochem. important lectin, jacalin, play significant roles in many biol. functions. It is highly desirable to develop a simple but efficient method to selectively detect lectin proteins. Here the authors report the development of carbohydrate containing responsive hydrogel sensing materials for the selective detection of lectin proteins. The copolymerization of a vinyl linked carbohydrate monomer with acrylamide and acrylic acid forms a carbohydrate hydrogel that shows specific “”multivalent”” binding to lectin proteins. The resulting carbohydrate hydrogels are attached to 2-D photonic crystals (PCs) that brightly diffract visible light. This diffraction provides an optical readout that sensitively monitors the hydrogel volume The authors use lactose, galactose, and mannose containing hydrogels to fabricate a series of 2-D PC sensors that show strong selective binding to the lectin proteins ricin, jacalin, and Con A. This binding causes a carbohydrate hydrogel shrinkage which significantly shifts the diffraction wavelength. The resulting 2-D PC sensors can selectively detect the lectin proteins ricin, jacalin, and Con A. These unoptimized 2-D PC hydrogel sensors show a limit of detection (LoD) of 7.5 × 10-8 M for ricin, a LoD of 2.3 × 10-7 M for jacalin, and a LoD of 3.8 × 10-8 M for Con A, resp. This sensor fabrication approach may enable numerous sensors for the selective detection of numerous lectin proteins.

ACS Sensors published new progress about Biosensors. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, HPLC of Formula: 2595-07-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Balcerzak, Anna K. published the artcileStructurally diverse disaccharide analogs of antifreeze glycoproteins and their ability to inhibit ice recrystallization, Quality Control of 2595-07-5, the main research area is structure activity antifreeze glycoprotein inhibit ice recrystallization disaccharide preparation; galactosamine disaccharide preparation antifreeze glycoprotein inhibit ice recrystallization.

The β-D-galactosyl-(1,3)-α-N-acetyl-D-galactosamine disaccharide is present in antifreeze glycoproteins (AFGPs). Analogs of this disaccharide including the β-linked (1,3)-, (1,4)-, and (1,6)-galactosyl-N-acetyl galactosamine and the β-(1,3)-galactosyl-galactoside were synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The results from this study demonstrate that the β-linked-(1,4) disaccharide exhibits more potent IRI activity than the native β-linked-(1,3) disaccharide. The C2 N-acetyl group of the disaccharide does not affect IRI activity but in monosaccharides, the presence of the C2 N-acetyl group decreases IRI activity. The current study will facilitate the design of potent small-mol. ice recrystallization inhibitors.

Bioorganic & Medicinal Chemistry Letters published new progress about Antifreeze. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, Quality Control of 2595-07-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Nkosana, Noreen K. published the artcileSynthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A, COA of Formula: C9H16O6, the main research area is drug resistance heptosyltransferase inhibition KDO ulosonic acid preparation; protein dynamic mechanism inhibition HepI enzyme antibiotic antibacterial; mol docking enzyme substrate inhibitor allosteric binding conformation; lipid monosaccharide Escherichia coli kinetic synthesis heptosyltransferase inhibition; Allosterism; AutoDock Vina; GT-B; Glycosyltransferase; Heptosyltransferase; Inhibition kinetics; Inhibitor design; LPS; Lipopolysaccharide; Structural rearrangement.

Gram-neg. bacteria comprise the majority of microbes that cause infections that are resistant to pre-existing antibiotics. The complex cell wall architecture contributes to their ability to form biofilms, which are often implicated in hospital-acquired infections. Biofilms promote antibiotic resistance by enabling the bacteria to survive hostile environments such as UV radiation, pH shifts, and antibiotics. The outer membrane of Gram-neg. bacteria contains lipopolysaccharide (LPS), which plays a role in adhesion to surfaces and formation of biofilms. The main focus of this work was the synthesis of a library of glycolipids designed to be simplified analogs of the Lipid A, the membrane embedded portion component of LPS, to be tested as substrates or inhibitors of Heptosyltransferase I (HepI or WaaC, a glycosyltransferase enzyme involved in the biosynthesis of LPS). Fourteen analogs were synthesized successfully and characterized. While these compounds were designed to function as nucleophilic substrates of HepI, they all demonstrated mild inhibition of HepI. Kinetic characterization of inhibition mechanism identified that the compounds exhibited uncompetitive and mixed inhibition of HepI. Since both uncompetitive and mixed inhibition result in the formation of an Enzyme-Substrate-inhibitor complex, mol. docking studies (using AutoDock Vina) were performed, to identify potential allosteric binding site for these compounds The inhibitors were shown to bind to a pocket formed after undergoing a conformational change from an open to a closed active site state. Inhibition of HepI via an allosteric site suggest that disruption of protein dynamics might be a viable mechanism for the inhibition of HepI and potentially other enzymes of the GT-B structural class.

Bioorganic & Medicinal Chemistry Letters published new progress about Allosterism. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, COA of Formula: C9H16O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Gigg, Roy published the artcileUse of the allyl ether as a protecting group in a new synthesis of L-lyxose, Recommanded Product: (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, the main research area is .

Crystalline 2,3,4-tri-O-benzyl-D-galactose was prepared from allyl 6-O-allyl- 2,3,4-tri-O-benzyl-α-D-galactopyranoside by isomerization of the allyl groups to prop-1-enyl groups and removal by dilute-acid hydrolysis. Reduction by NaBH4 gave crystalline 2,3,4-tri-O-benzyl-D- galactitol which was converted into 2,3,4-tri-O-benzyl-L-lyxose by oxidation with NaIO4. Catalytic hydrogenation gave L-lyxose.

Journal of the Chemical Society published new progress about Allyl group. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, Recommanded Product: (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Choutka, Jan published the artcileStraightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals, Related Products of alcohols-buliding-blocks, the main research area is hydroxyglycal chlorination dehydrochlorination glycosyl chloride protecting group monosaccharide; 2-Hydroxyglycals; Carbohydrates; Dehydrochlorination; Glycals; Glycosyl chlorides.

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehydrochlorination reactions were studied on a range of glycosyl chlorides to provide suitable reaction conditions for this transformation. Benzyl ether, isopropylidene and benzylidene protecting groups, as well as inter-glycosidic linkage, were found to be compatible with this protocol. The described method is operationally simple and allows for the quick preparation of 2-hydroxyglycals with other than ester protecting groups, providing a feasible alternative to existing methods.

Carbohydrate Research published new progress about Chlorination. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, Related Products of alcohols-buliding-blocks.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Gerbst, Alexey G. published the artcileDriving Force of the Pyranoside-into-Furanoside Rearrangement, Formula: C9H16O6, the main research area is pyranoside furanoside rearrangement.

Ab initio calculations of fully O-sulfated model monosaccharides, including common hexoses (glucose, galactose, fucose, and mannose) and pentoses (arabinose and xylose), were performed to study the energetic properties of the recently discovered pyranoside-into-furanoside (PIF) rearrangement. It was shown that the per-O-sulfated derivatives of furanoside isomers generally had lower energies than the corresponding per-O-sulfated pyranosides, while nonsulfated furanosides were always less favored than nonsulfated pyranosides. Mannose, which is known to be unreactive in PIF rearrangement, was the only exception. The results of the theor. calculations were confirmed by exptl. studies of monosaccharide models and explained the driving force of such unusual ring contraction process as PIF rearrangement. The conclusions of performed investigation can be used for prediction of new substrates applicability for PIF rearrangement.

ACS Omega published new progress about Conformation. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, Formula: C9H16O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Russo, Laura published the artcileThiol-ene Mediated Neoglycosylation of Collagen Patches: A Preliminary Study, COA of Formula: C9H16O6, the main research area is thiol ene neoglycosylation collagen patch surface treatment.

Despite the relevance of carbohydrates as cues in eliciting specific biol. responses, the covalent surface modification of collagen-based matrixes with small carbohydrate epitopes has been scarcely investigated. We report thereby the development of an efficient procedure for the chemoselective neoglycosylation of collagen matrixes (patches) via a thiol-ene approach, between alkene-derived monosaccharides and the thiol-functionalized material surface. Synchrotron radiation-induced XPS (SR-XPS), Fourier transform-IR (FT-IR), and enzyme-linked lectin assay (ELLA) confirmed the effectiveness of the collagen neoglycosylation. Preliminary biol. evaluation in osteoarthritic models is reported. The proposed methodol. can be extended to any thiolated surface for the development of smart biomaterials for innovative approaches in regenerative medicine.

Langmuir published new progress about Collagen type I Role: RCT (Reactant), RACT (Reactant or Reagent). 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, COA of Formula: C9H16O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Holme, Kevin R. published the artcileN-[2-(Glycosyloxy)ethyl]chitosan derivatives. Part I. Preparation and characterization of N-[2-(glycosyloxy)ethyl]chitosan derivatives., Name: (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, the main research area is chitosan glycosyloxyethyl preparation water solubility; glycosyloxyethylchitosan preparation water solubility; allyl glycoside preparation carbon proton NMR; ozonolysis allyl glycoside; reduction alkylation chitosan oxoethyl formylmethyl glycoside.

Allyl glycosides of 8 simple sugars were prepared and characterized, including 1H- and 13C-NMR assignments. Formylmethyl glycosides, obtained by reductive ozonolysis of the allyl glycosides, were reductively N-alkylated to chitosan with typical yields of 80%. The glycosides of α- and β-D-glucopyranose, α- and β-D-galactopyranose, 2-acetamido-2-deoxy-α- and β-D-glucopyranose, β-D-glucuronic acid, and β-lactose were incorporated by this method. The degree of substitution (d.s.) of the products was controlled by varying the molar ratio of glycoside to free amine groups of chitosan by between 0.5 and 3.0. Derivatives of degree of substitution > 0.3 were typically water soluble, and compounds of higher d.s. generally gave less-viscous aqueous solutions Assignment of 13C-NMR chem. shifts verified the structure of these derivatives The linewidths of the branch resonances (5-100 Hz) provided qual. information about the relationship between d.s. and branch mobility. The resonances of high-d.s. products were narrower and more intense than analogous low-d.s. derivatives The chitosan resonances of the backbone were generally broader (50-200 Hz) and less intense, and as a result were difficult to assign fully.

Carbohydrate Research published new progress about Carbohydrates Role: SPN (Synthetic Preparation), PREP (Preparation). 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, Name: (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Farkas, Erzsebet published the artcileEnzymatic synthesis of galactose-containing disaccharides employing β-galactosidase from Bacillus circulans, COA of Formula: C9H16O6, the main research area is galactose disaccharide enzymic preparation; carbohydrate enzymic galactosylation.

Galβ1â†? disaccharide structures are vital core units of the oligosaccharide components of glycoconjugates. β-Galactosidase from Bacillus circulans (E.C.3.2.1.23) catalyzes the transfer of galactose from a donor structure such as GalβOpNP to various GlcNAc and galactose derivatives, forming β1â†? linkages. The synthesis of several biol. relevant disaccharides [Galβ1â†?GlcNAcαOAll, Galβ1â†?GlcNAcβOAll, Galβ1â†?GalαOAll, Galβ1â†?GalβOAll, Galβ1â†?GalβSPh, Galβ1â†?GalβOpNP] and the trisaccharide Galβ1â†?Galβ1â†?GalβOpNP was achieved in 30-66% yield by application of this enzyme.

European Journal of Organic Chemistry published new progress about Disaccharides Role: SPN (Synthetic Preparation), PREP (Preparation). 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, COA of Formula: C9H16O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts