Category: 2595-07-5

James, Kenneth published the artcileThe synthesis of per-O-benzyl-α-D-galactosyl and -α-L-fucosyl bromides, Related Products of alcohols-buliding-blocks, the main research area is hexopyranosyl perbenzylated bromide; galactopyranosyl perbenzylated bromide; fucopyranosyl perbenzylated bromide; benzylated hexopyranosyl bromide.

The title galactosyl bromide was prepared by benzylation of allyl galactopyranoside, with PhCH2Br-NaH, isomerization of the allyl group with tert-BuOK-Me2SO to prop-1-enyl tetra-O-benzyl-β-D-galactopyranoside. Removal of the vinyl residue with HgO and reaction with p-O2NC6H4COCl gave the tetra-O-benzyl-1-O-p-nitrobenzoyl-D-galactopyranose (I). Treatment of I with HBr gave 80% of the α-bromide as an oil. The fucopyranosyl derivative was prepared similarly.

Australian Journal of Chemistry published new progress about hexopyranosyl perbenzylated bromide; galactopyranosyl perbenzylated bromide; fucopyranosyl perbenzylated bromide; benzylated hexopyranosyl bromide. 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

Rossi, Marco published the artcileSeparation of O- and C-allyl glycoside anomeric mixtures by capillary electrophoresis and high-performance liquid chromatography, Related Products of alcohols-buliding-blocks, the main research area is allyl glycoside anomer capillary electrophoresis liquid chromatog.

Rapid and reliable methods for the anal. of O- and C-allyl galactopyranosides and glucopyranosides are presented, based on capillary zone electrophoresis (CZE) and micellar electrokinetic capillary chromatog. (MEKC). In MEKC, the formation of chromophoric and charged complexes between the saccharides and borate as well as the hydrophobic interactions with micelles jointly contributed to the selective separation and sensitive detection of all the investigated anomeric couples. Some non-purified synthesis mixtures of C-allyl glycosides were successfully characterized without pre-treatment. MEKC buffer conditions for which glycosides separation was successfully achieved were then exported and applied to reverse-phase liquid chromatog. (RP-HPLC), for the quant. isolation of each allyl glycoside anomer. Identification of the obtained anomeric products was performed by electrospray mass spectrometry and 13C NMR spectroscopy. Glycoside-solvent interactions driving the selective anomeric separation were shortly addressed and discussed on the basis of sugar derivatives structural differences.

Journal of Chromatography A published new progress about Anomers. 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

Rauter, Marion published the artcileSynthesis of benzyl β-D-galactopyranoside by transgalactosylation using a β-galactosidase produced by the over expression of the Kluyveromyces lactis LAC4 gene in Arxula adeninivorans, Related Products of alcohols-buliding-blocks, the main research area is benzyl beta galactopyranoside transgalactosylation galactosidase Kluyveromyces LAC4 Arxula.

The LAC4 gene of Kluyveromyces lactis encoding for β-galactosidase was overexpressed in the yeast Arxula adeninivorans to produce the enzyme, which can be used for the synthesis of β-D-galactosides. These compounds play a major role as precursors for the synthesis of glycolipids and glycoproteins in medicine or for the production of tensides. The Xplor2 transformation/expression platform was used because it enabled stable integration of the gene in the Arxula genome and the production of high levels of the enzyme. The recombinant β-galactosidase, fused with C-terminal His-tag region (Lac4-6hp), was purified by precipitation with ammonium sulfate and FPLC using hydroxylapatite. The enzyme exhibited optimal activity at 37 to 40°, pH 6.5 in 50 mM sodium acetate buffer. Activity was measured by the formation of p-nitrophenol at 405 nm from the hydrolyzed chromogenic substrate, p-nitrophenyl-β-D-gal. Biochem. characterization included the calculation of Km and apparent kcat values of the enzyme. The formation of benzyl β-D-gal by 0.1 U enzyme from A. adeninivorans with transgalactosylation was six times higher than that for the prokaryotic enzyme from E. coli. Moreover, the partially purified enzyme was used for the selective hydrolysis of allyl β-D-gal in a mixture of allyl β- and allyl α-D-gal, with 4 g l-1 being hydrolyzed within one day by 1 U ml-1. Thus, the recombinant β-galactosidase produced in A. adeninivorans is of potential interest for the enzymic synthesis of benzyl β-D-gal and other galactosides as well as the selective hydrolysis of anomeric mixtures and could be used to replace difficult chem. procedures.

Journal of Molecular Catalysis B: Enzymatic published new progress about Anomers. 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

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

Kartha, Ravindranathan K. P. published the artcileSimple and efficient strategy for making β-(1→6)-linked galactooligosaccharides using ‘naked’ galactopyranosides as acceptors, Computed Properties of 2595-07-5, the main research area is galactooligosaccharide beta linked preparation; galactopyranoside unprotected regioselective stereoselective glycosidation acetobromosugar.

Unprotected (naked) galactopyranosides were used for the first time in the direct regio- and stereoselective synthesis of β-(1→6)-linked oligosaccharides in 75-90% yield by coupling them with acetobromosugars in the presence of silver carbonate in dichloromethane. β-(1→4)-Linked oligosaccharides (yield 5-10%) were the byproducts. Thus, glycoside I (OSE = OCH2CH2SiMe3)was reacted with bromide II in the presence of Ag2CO3 in CH2Cl2 to give the disaccharide III (R = H).

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about Glycosylation. 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, Computed Properties of 2595-07-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Blinkovsky, Alexander M. published the artcileEnzymic derivatization of saccharides and their chemical polymerization, Recommanded Product: (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, the main research area is propargyl galactopyranoside preparation polymerization; allyl galactopyranoside preparation polymerization; hydrophilic polymer sugar; oligosaccharide transglycosidation enzymic propargyl allyl alc.

The enzymic synthesis of sugar-based acetylene and ethylene derivatives as precursors to hydrophilic polymers is described. Propargyl and allyl alcs. have been used as glycosyl acceptors in the transglycosylation reactions of glycosidases with various disaccharides including lactose, maltose, and cellobiose. Reaction of propargyl and allyl alcs. with lactose catalyzed by β-galactosidase resulted in the formation of propargyl-β-D-galactopyranoside and allyl-β-D-galactopyranoside in 42 and 13% yields, resp. Polymerization of propargyl-β-D-galactopyranoside with AlBr3 in ethanol resulted in the formation of oligomeric poly(acetylenic) species (MW = 1,300). Free radical polymerization of allyl-β-D-galactopyranoside in DMF or water resulted in poly(ethylenic) species with MW > 30,000. The combined enzymic and chem. reactions inherent in these syntheses provide a unique approach in the preparation of hydrophilic polymers containing sugars and their derivatives

Tetrahedron: Asymmetry published new progress about Disaccharides 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, Recommanded Product: (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Lee, Reiko T. published the artcileSynthesis of 3-(2-aminoethylthio)propyl glycosides, HPLC of Formula: 2595-07-5, the main research area is allyl alc glycoside addition; ethylthiopropyl glycoside; glucopyranoside ethylthiopropyl; galactopyranoside ethylthiopropyl.

Anomeric pairs of 3-(2-aminoethylthio)propyl D-galactopyranoside D-glucopyranoside and 2-acetamido-2-deoxy-D-glucopyranoside were prepared by addition of H2N(CH2)2SH to the corresponding anomeric allyl glycosides. The allyl α-glycosides were prepared by refluxing the sugars with allyl alc. in the presence of an acid catalyst; the allyl β-glycosides were prepared by the reaction of acetylated glycosyl bromides with allyl alc. in the presence of Hg(CN)2 followed by O-deacetylation. The rate of thiol addition to the allylic group was different for each glycoside.

Carbohydrate Research published new progress about Glycosides 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, HPLC of Formula: 2595-07-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Nilsson, Kurt G. I. published the artcileA simple strategy for changing the regioselectivity of glycosidase-catalyzed formation of disaccharides. Part II. Enzymic synthesis in situ of various acceptor glycosides, Application In Synthesis of 2595-07-5, the main research area is galactopyranoside acceptor preparation; transglycosidation lactose galactosidase; raffinose transglycosidation; galactopyranosylgalactopyranoside disaccharide.

β-D-Galactosidase induced the formation of allyl, benzyl, and trimethylsilylethyl β-D-galactopyranosides on a 1-20 g scale from lactose and allyl alc., benzyl alc., and trimethylsilylethanol. Similarly, α-D-galactosidase catalyzed the formation of allyl α-D-galactopyranoside from raffinose and allyl alc. The galactosides were used as acceptors for the preparation of several galactopyranosylgalactopyranoside disaccharides.

Carbohydrate Research published new progress about Glycosides 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, Application In Synthesis of 2595-07-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts