143289-25-2

Upstream product

• 498-07-7 levoglucosan 
• 71-36-3 butan-1-ol 
• 5391-18-4 butyl-α-D-glucopyranoside 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 63119-23-3 1-butyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 69-79-4 D-maltose 
• 35599-02-1 4-nitrophenyl-β-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 6697-88-7 2,3,4,6-tetra-O-acetyl-1-n-butyl-β-D-glucopyranoside 
• 9004-34-6 cellulose 
• 50-99-7 D-glucose 

Downstream Products

• 5391-18-4 butyl-α-D-glucopyranoside 
• 492-61-5 β-D-glucose 
• 71-36-3 butan-1-ol 
• 25320-96-1 O-n-pentyl β-D-glucopyranoside 
• 39824-11-8 n-hexyl-β-D-glucopyranoside 
• 78617-12-6 n-heptyl beta-D-glucopyranoside 
• 25320-91-6 propyl β-D-glucopyranoside 
• 29836-26-8 n-octyl β-D-glucopyranoside 
• 69984-73-2 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-nonyloxy-tetrahydro-pyran-3,4,5-triol 
• 153323-26-3 butyl 6-O-stearoyl-α-D-glucopyranoside 
• 5391-18-4 n-butyl β-D-glucopyranoside 
• 252190-07-1 n-butyl-6-O-trityl-α-glucopyranoside 
• 50-99-7 D-glucose 
• 29781-80-4 octyl alpha-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of butyl-α and β-D-glucopyranosides in the presence of dealuminated H-Y faujasites: Kinetic study, mechanism, stereoelectronic effects, and microreversibility principle

The glycosylation reaction between D-glucose and n-butanol has been investigated over various dealuminated HY zeolites with Si/Al ratios from 2.5 to 100. In this way, butyl-α- and β-D-glucofuranosides and -pyranosides are readily synthesized at temperatures from 363 to 383 K and with a butanol/glucose ratio from 5 to 40. From the systematic study of the glycosylation reaction, a kinetic scheme involving both consecutive and competitive steps has been proposed. Butyl-D-glucofuranosides and butyl-D-glucopyranosides are primary products, butyl-D-glucofuranosides being then quantitatively converted into their pyranoside form. The use of microporous catalysts, associated with their shape selectivity properties, reduces the amount of oligomers and increases the amount of β-D-glucopyranosides in a significant manner. The β/α anomeric ratios observed are then discussed in terms of stereoelectronic effects which are, according to the principle of microreversibility of the same nature as those reported for the reverse reaction, i.e., hydrolysis of alkyl-D-glucopyranosides.

Selective Primary Alcohol Oxidation of Lignin Streams from Butanol-Pretreated Agricultural Waste Biomass

Chemically modified lignins are important for the generation of biomass-derived materials and as precursors to renewable aromatic monomers. A butanol-based organosolv pretreatment has been used to convert an abundant agricultural waste product, rice husks, into a cellulose pulp and three additional product streams. One of these streams, a butanol-modified lignin, was oxidized at the γ position to give a carboxylic acid functionalized material. Subsequent coupling of the acid with aniline aided lignin characterization and served as an example of the flexibility of this approach for grafting side chains onto a lignin core structure. The pretreatment was scaled up for use on a multi-kilogram scale, a development that enabled the isolation of an anomeric mixture of butoxylated xylose in high purity. The robust and scalable butanosolv pretreatment has been developed further and demonstrates considerable potential for the processing of rice husks.

Cellulose conversion into alkylglycosides in the ionic liquid 1-butyl-3-methylimidazolium chloride

The conversion of cellulose into alkylglycosides is carried out in the ionic liquid 1-butyl-3-methylimidazolium chloride in the presence of an acidic catalyst. Primary alcohols like n-butanol and n-octanol were used as alkylating reagents. The acidic resin Amberlyst 15DRY proved to be the optimum heterogeneous catalyst: it catalyzes the hydrolysis of the β(1→4) links in the cellulose polymeric chain as well as the alkylation of the hydroxyl groups at the C1 position of the glucose intermediate. The cellulose was fully converted under mild conditions; in a reaction with n-butanol, the obtained yield of butylglucopyranoside isomers was 86%.

Preparation of salidroside with n-butyl β-D-glucoside as the glycone donor via a two-step enzymatic synthesis catalyzed by immobilized β-glucosidase from bitter almonds

β-Glucosidase from bitter almonds was immobilized on epoxy group-functionalized beads for catalyzing salidroside synthesis in a two-step process with n-butyl-β-D-glucoside (BG) as the glucosyl donor. The formation of salidroside ((0.59 ± 0.02) M) at a yield of 39.04%±1.25% was accomplished in 8 h by the transglucosylation of immobilized β-glucosidase at pH?8.0 and 50 °C when the ratio of BG to tyrosol was 1:2 (mol/mol). A study on the influence of different glycosyl acceptors demonstrated that the yield of the glucosylation reaction of phenylmethanol and cyclohexanol was higher than that of either phenol or cyclohexanol. This may account for the selectivity of the immobilized enzyme towards the alcoholic hydroxyl group of tyrosol in the salidroside synthesis reaction. A study on the synthesis of BG via the reverse hydrolysis of immobilized β-glucosidase showed that a yield of 78.04%±2.2% BG can be obtained with a product concentration of (0.23 ± 0.015) M.

Influence of acyl groups on glucopyranoside reactivity in Lewis acid promoted anomerisation

Lewis acid promoted anomerisation has potential in O- or S-glycoside synthesis. Herein, the anomerisation kinetics of thirty-one β-D-glucopyranosides was determined to determine how particular acyl protecting groups and their location influence reactivity towards a Lewis acid promoted reaction. The replacement of acetyl groups with benzoyl groups led to reduced reactivity when located at O-3, O-4 and O-6. However a reactivity increase was observed when the acetyl group was replaced by a benzoyl group at O-2. The 2,3,4,6-tetra-O-(4-methoxy)benzoate had an ～2-fold increase in rate when compared to the tetrabenzoate.

ALKENYL GLYCOSIDES AND THEIR PREPARATION

An alkenyl glycoside is prepared by reacting a metathesis-derived unsaturated fatty alcohol containing 10 to 30 carbon atoms with either (1) a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide, or (2) a hydrocarbyl glycoside produced by reacting an alcohol containing up to 6 carbon atoms with a reducible monosaccharide or composition hydrolyzable to a reducible monosaccharide. Each of these reactions is performed in the presence of an acid catalyst and under conditions sufficient to form the alkenyl glycoside or hydrocarbyl glycoside. The preferred alkenyl glycosides are 9-decen-1-yl glycoside; 9-dodecen-1-yl glycoside; 9-tridecen-1-yl glycoside; 9-pentadecen-1-yl glycoside; 9-octadecen-yl glycoside; or 9-octadecen-1,18-diyl glycoside.

Glycosylation mediated - BAIL in aqueous solution

The use of Br?nsted acid ionic liquid (BAIL) as a catalyst for the activation of unreactive and unprotected glycosyl donors has been demonstrated for the first time in aqueous solution.

Purification, characterization, and gene identification of an α-glucosyl transfer enzyme, a novel type α-glucosidase from Xanthomonas campestris WU-9701

The α-glucosyl transfer enzyme (XgtA), a novel type α-glucosidase produced by Xanthomonas campestris WU-9701, was purified from the cell-free extract and characterized. The molecular weight of XgtA is estimated to be 57 kDa by SDS-PAGE and 60 kDa by gel filtration, indicating that XgtA is a monomeric enzyme. Kinetic properties of XgtA were determined for α-glucosyl transfer and maltose-hydrolyzing activities using maltose as the α-glucosyl donor, and if necessary, hydroquinone as the acceptor. The Vmax value for α-glucosyl transfer activity was 1.3 × 10-2 (mM/s); this value was 3.9-fold as much as that for maltose-hydrolyzing activity. XgtA neither produced maltooligosaccharides nor hydrolyzed sucrose. The gene encoding XgtA that contained a 1614-bp open reading frame was cloned, identified, and highly expressed in Escherichia coli JM109 as the host. Site-directed mutagenesis identified Asp201, Glu270, and Asp331 as the catalytic sites of XgtA, indicating that XgtA belongs to the glycoside hydrolase family 13.

Isolation and characterization of a novel α-glucosidase with transglycosylation activity from Arthrobacter sp. DL001

A strain of Arthrobacter sp. DL001 with high transglycosylation activity was successfully isolated from the Yellow Sea of China. To purify the extracellular enzyme responsible for transglycosylation, a four-step protocol was adopted and the enzyme with electrophoretical purity was obtained. The purified enzyme has a molecular mass of 210 kDa and displays a narrow hydrolysis specificity towards α-1,4-glucosidic bond. Its hydrolytic activity was identified as decreasing in the order of maltotriose > panose > maltose. Only 3.61% maltose activity occurs when p-nitrophenyl α-d-glycopyranoside serves as a substrate, suggesting that this enzyme belongs to the type II α-glucosidase. In addition, the enzyme was able to transfer glucosyl groups from the donors containing α-1,4-glucosidic bond specific to glucosides, xylosides and alkyl alcohols in α-1,4- or α-1,6-manners. A decreased order of activity was observed when maltose, maltotriose, panose, β-cyclodextrin and soluble starch served as glycosyl donors, respectively. When maltose was utilized as a donor and a series of p-nitrophenyl-glycosides as acceptors, the glucosidase was capable of transferring glucosyl groups to p-nitrophenyl-glucosides and p-nitrophenyl-xylosides in α-1,4- or α-1,6-manners. The yields of p-nitrophenyl-oligosaccharides could reach 42-60% in 2 h. When a series of alkyl alcohols were utilized as acceptors, the enzyme exhibited its transglycosylation activities not only to the primary alcohols but also to the secondary alcohols with carbon chain length 1-4. Therefore, all the results indicated that the purified α-glucosidase present a useful tool for the biosynthesis of oligosaccharides and alkyl glucosides.

Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

An array of ten β-D-glucopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl β-D-glucoside increased from 1.9% to 6.1% when the water content was reduced from 10% to 5% (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl β-D-glucoside was found to have significant surface activity as well.