29836-26-8Relevant academic research and scientific papers
Enzymatic synthesis of octyl glucoside catalyzed by almond β-glucosidase in organic media
Ducret, Amelie,Carriere, Jean-Francois,Trani, Michael,Lortie, Robert
, p. 653 - 656 (2002)
The synthesis of n-octyl-β-D-glucopyranoside can be performed by direct condensation of 1-octanol and glucose, catalyzed by immobilized almond β-glucosidase, using solid glucose suspended in 1-octanol as a reaction media. Both the rate of reaction and the conversion could be enhanced by using acetonitrile and N,N-dimethylformamide (DMF) as co-solvents, the latter giving the best results. The rate of reaction was dependent on the concentration of DMF and on the initial water activity (aw), with higher water activity fostering faster reactions. The rate increased with DMF concentration, up to 20% DMF, but diminished rapidly at higher concentrations. Product concentration could be increased from 40 to 100 mM by going from 0 to 20% DMF; however, it was not sensitive to the initial water activity.
Synthesis of Alkyl Glycosides Catalyzed by β-Glycosidases in a System of Reverse Micelles
Kouptsova,Klyachko,Levashov
, p. 380 - 384 (2001)
A basic possibility of enzymic synthesis of alkyl glycosides in a system of the Aerosol-OT (AOT) reverse micelles was studied. Octyl β-D-galactopyranoside and octyl β-D-glucopyranoside were synthesized from the corresponding sugars (lactose or glucose) and octyl alcohol under catalysis with glycolytic enzymes, β-galactosidase and β-glucosidase, respectively. The transglycosylation/hydrolysis ratio was shifted toward transglycosylation by using octyl alcohol, one of the substrates, as an organic solvent. The alkyl glycosides were thus obtained in one step from a hydrophilic mono- or disaccharide and a hydrophobic aliphatic alcohol. The direction of the reaction was shown to depend on the pH of aqueous solution solubilized in reverse micelles. The maximum yields were 45% and 40% for octyl galactoside and octyl glucoside, respectively; they markedly exceeded the yields of enzymic syntheses in a two-phase system reported previously.
Synthesis of octyl glucopyranoside by almond β-glucosidase adsorbed onto Celite R-640
Basso, Alessandra,Ducret, Amélie,Gardossi, Lucia,Lortie, Robert
, p. 2005 - 2008 (2002)
The synthesis of octyl glucoside from p-nitrophenyl glucopyranoside (p-NPG) and 1-octanol was carried out with almond β-glucosidase adsorbed onto Celite R-640. The influence of the amount of water added to the system as well as the addition of co-solvents
Improved octyl glucoside synthesis using immobilized β-glucosidase on PA-M with reduced glucose surplus inhibition
Wang, Feng,Ma, Yong,Liu, Yan-Hua,Zhang, Xuan,Zhang, Fuming,Linhardt, Robert J.
, p. 349 - 362 (2017)
A β-glucosidase extracted from bitter almond (Prunus dulcis var. amara) was immobilized on polyamine microspheres (PA-M) for catalytic octyl glucoside (OG) synthesis from glucose and octanol through reversed hydrolysis. The immobilization increased the activity of enzyme at pH 6.0–7.0, and the optimal reaction temperature for immobilized enzyme was identical to the free enzyme. The thermal stability and solvent tolerance of enzyme were increased by its immobilization. In the co-solvent system using 10% t-butyl alcohol and 10% (v/v) water, the yield of OG was increased by 1.7-fold compared to the yield from the system without co-solvent. Based on dynamic and Dixon plot analyses, the initial reaction velocity (V0) increased approximately three-fold on immobilization and the OG synthesis was inhibited by surplus glucose. The inhibition dissociation constants for free and immobilized enzyme were 219 mM and 116 mM, respectively. A fed-batch mode was applied in the OG synthesis to minimize substrate inhibition. After 336 h of reaction, the OG yield and the conversion rate of glucose reached 134 mM and 59.6%, respectively. Compared to the batch operation, the fed-bath operation increased the OG yield and the conversion rate of glucose by 340% and 381%, respectively.
Development of novel inhibitors specific for human heparanase-1
Ohmae, Masashi,Fujita, Yuki,Takada, Junko,Kimura, Shunsaku
, p. 797 - 798 (2013)
The octylglycosides 1-3 having heparan sulfate fragments were designed as inhibitors specific for human heparanase-1. Inhibition experiments for the heparanase revealed the inhibitory effects of 1 and 3 (IC50 = 6 and 1.4mM, respectively). It was difficult for compound 2 to inhibit the heparanase activity. Furthermore, the inhibitory action of 3 was specific for the heparanase, whereas 1 and 2 also inhibited the hydrolysis activity of exoenzyme β-glucuronidase from bovine liver.
Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters
Matin, Mohammed M.,Bhattacharjee, Sreebash C.,Chakraborty, Priyanka,Alam, Muhammad S.
supporting information, (2019/10/10)
Octyl β-D-glucopyranoside (OBG), prepared from D-glucose and octan-1-ol employing MW method, was subjected to direct dimolar valeroylation in pyridine at room temperature (25 °C) with valeroyl chloride. This mainly furnished the corresponding 3,6-di-O-valeroate in 57% yield indicating the regioselectivity at C-6 and C-3 positions. For structural elucidation and to get newer glucopyranosides of potential antimicrobial 3,6-di-O-valeroate was further converted into four novel 2,4-di-O-acyl esters reasonably in good yields. Per-O-acetate and per-O-benzoate of OBG were also prepared for SAR study. PASS predication and in vitro antimicrobial studies established them as better antifungal agent than that of antibacterial. SAR study along with AdmetSAR and SwissADME suggested that incorporation of alkanoyl and aromatic ester groups on octyl glucopyranoside core increase antimicrobial potentiality in very low concentration (10 μgmL?1). Molecular docking revealed that novel 2,4-di-O-tosyl ester and 2,3,4,6-tetra-O-benzoyl ester may act as competitive inhibitors of lanosterol 14-alpha demethylase.
Estrogenicity of octyl glucoside synthesized by direct glucosidation as non-endocrine disruptive surfactant
Chung, Kyong-Hwan,Kim, Hangun,Park, Young-Kwon,Kim, Byung-Hoon,Kim, Jung-Sik,Jung, Sang-Chul
, p. 1478 - 1481 (2017/12/12)
The estrogenicity of octyl glucoside was studied with its preparation method using microporous zeolites. Its estrogenicity was estimated using E-assay method to confirm the possibility as nonendocrine disruptive surfactant. The octyl glucoside was synthesized from D-glucose with 1-octanol by direct glucosidation. The high conversion of D-glucose was obtained on H-FAU zeolite which has a mild acid strength. The conversion and yield were improved with increasing of acid site amount of the zeolite catalysts. The octyl glucopyranoside is more hydrophilic than nonylphenol and has a high wettability. The octyl glucosides represented extremely lower estrogenic cell proliferation compared with nonylphenol.
Sweet surfactants: Packing parameter-invariant amphiphiles as emulsifiers and capping agents for morphology control of inorganic particles
Voggel, Michael,Meinusch, Rebecca M.,Siewert, Vanessa,Kunkel, Marius,Wittmann, Valentin,Polarz, Sebastian
, p. 7214 - 7227 (2018/09/26)
Surfactants are not only pivotal constituents in any biological organism in the form of phospholipids, they are also essential for numerous applications benefiting from a large, internal surface, such as in detergents, for emulsification purposes, phase transfer catalysis or even nanoparticle stabilization. A particularly interesting, green class of surfactants contains glycoside head groups. Considering the variability of glycosides, a large number of surfactant isomers become accessible. According to established models in surfactant science such as the packing parameter or the hydrophilic lipophilic balance (HLB), they do not differ from each other and should, thus, have similar properties. Here, we present the preparation of a systematic set of glycoside surfactants and in particular isomers. We investigate to which extent they differ in several key features such as critical aggregation concentration, thermodynamic parameters, etc. Analytical methods like isothermal titration calorimetry (ITC), tensiometry, dynamic light scattering (DLS), small angle-X-ray scattering (SAXS), transmission electron microscopy (TEM) and others were applied. It was found that glycosurfactant isomers vary in their emulsification properties by up to two orders of magnitude. Finally, we have investigated the role of the surfactants in a microemulsion-based technique for the generation of zinc oxide (ZnO) nanoparticles. We found that the choice of the carbohydrate head has a marked effect on the shape of the formed inorganic nanocrystals.
Molecular Characterization and Potential Synthetic Applications of GH1 β-Glucosidase from Higher Termite Microcerotermes annandalei
Arthornthurasuk, Siriphan,Jenkhetkan, Wantha,Suwan, Eukote,Chokchaichamnankit, Daranee,Srisomsap, Chantragan,Wattana-Amorn, Pakorn,Svasti, Jisnuson,Kongsaeree, Prachumporn T.
, p. 877 - 894 (2018/05/25)
A novel β-glucosidase from higher termite Microcerotermes annandalei (MaBG) was obtained via a screening method targeting β-glucosidases with increased activities in the presence of glucose. The purified natural MaBG showed a subunit molecular weight of 55?kDa and existed in a native form as a dimer without any glycosylation. Gene-specific primers designed from its partial amino acid sequences were used to amplify the corresponding 1,419-bp coding sequence of MaBG which encodes a 472-amino acid glycoside hydrolase family 1 (GH1) β-glucosidase. When expressed in Komagataella pastoris, the recombinant MaBG appeared as a ~ 55-kDa protein without glycosylation modifications. Kinetic parameters as well as the lack of secretion signal suggested that MaBG is an intracellular enzyme and not involved in cellulolysis. The hydrolytic activities of MaBG were enhanced in the presence of up to 3.5-4.5 M glucose, partly due to its strong transglucosylation activity, which suggests its applicability in biosynthetic processes. The potential synthetic activities of the recombinant MaBG were demonstrated in the synthesis of para-nitrophenyl-β-D-gentiobioside via transglucosylation and octyl glucoside via reverse hydrolysis. The information obtained from this study has broadened our insight into the functional characteristics of this variant of?termite GH1 β-glucosidase and its applications in bioconversion and biotechnology.
N-alkyl - β - D - glucopyranoside synthetic method
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Paragraph 0024; 0025; 0027, (2017/12/06)
The invention discloses a synthesizing method of n-alkyl-beta-D-glucopyranoside. The method includes the following steps of dissolving fully-acetylated glucopyranose, n-alkyl alcohol and anhydrous stannic chloride in anhydrous methylene dichloride, stirring the mixture to have a reaction for 20 min to 70 min at the room temperature, washing the mixture through a saturated sodium carbonate solution, collecting organic phases, conducting reduced pressure distillation to obtain 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside, dissolving the 1-n-alkyl-2,3,4,6-tetraacetyl-beta-D-glucopyranoside in methyl alcohol, adding sodium methylate to adjust the pH value to 9, having a reaction for 1.5 h at the room temperature, adjusting the pH value to be neutral through strong acid cation exchange resin, conducting filtering, steaming filtrate to obtain solvent, and drying the solvent to obtain the n-alkyl-beta-D-glucopyranoside. The n-alkyl is n-alkyl of C8-C12. The method is simple, raw materials are easy to obtain, cost is low, reaction temperature is moderate and easy to control, the method is environmentally friendly, and the prepared beta-configuration glucopyranoside is high in purity.
