25320-96-1Relevant academic research and scientific papers
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
Wang, Qinqqin,Yu, Huilei,Zhao, Na,Li, Chunxiu,Shang, Yazhuo,Liu, Honglai,Xu, Jianhe
, p. 275 - 280 (2016/04/10)
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.
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
Wang, Qinqqin,Yu, Huilei,Zhao, Na,Li, Chunxiu,Shang, Yazhuo,Liu, Honglai,Xu, Jianhe
, p. 275 - 280 (2012/06/29)
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.
POLYMER STABILIZER
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, (2010/08/03)
A polymer stabilizer comprising the following alkoxy compound: the alkoxy compound: a compound obtained by alkoxylating at least one hydroxyl group contained in a compound of the following formula (1) containing one formyl group or carbonyl group and (n?1) hydroxyl groups in the molecule with an alkyl group having 1 to 12 carbon atoms: [in-line-formulae]CnH2nOn??(1)[/in-line-formulae] (wherein, n represents an integer of 3 or more).
A new method of synthesis of alkyl β-glycosides using sucrose as sugar donor
Kino, Kuniki,Satake, Ryoko,Morimatsu, Takayuki,Kuratsu, Shoko,Shimizu, Yu,Sato, Masaru,Kirimura, Kohtaro
, p. 2415 - 2417 (2008/12/23)
Cellobiose phosphorylase from Clostridium thermocellum catalyzed the β-anomer-selective synthesis of alkyl glucosides from cellobiose. Synthesis of alkyl β-glucoside from inexpensive sucrose using cellobiose phosphorylase and sucrose phosphorylase from Pseudomonas saccharophilia was investigated. By combined use of these two phosphorylases, alkyl β-glucoside was anomer-selectively synthesized from sucrose and alkyl alcohol.
Novel reaction systems for the synthesis of O-glucosides by enzymatic reverse hydrolysis
Balogh, Teréz,Boross, László,Kosáry, Judit
, p. 679 - 682 (2007/10/03)
Our studies are presented to replace alcohols as solvents in reverse hydrolytic reactions catalyzed by immobilized β-glucosidase to synthesize O-substituted β-D-glucopyranosides in preparative-scale. We found that 1,2-diacetoxyethane is a suitable solvent and O-alkyl or aryl β-D-glucosides were synthesized in moderate yields (after isolation 12-19%). In these reactions proportion of glucose and glucosyl acceptor hydroxy compounds was 1:20. We suggest that 1,2-diacetoxyethane can be useful not only for alcohols but for other glucosyl donor compounds unsuitable for the role of solvent (e.g., phenols) in the synthesis of O-β-D-glucosides by reverse hydrolysis.
Use of n-pentenyl glycosides as precursors to various spacer functionalities
Buskas, Therese,Soederberg, Eva,Konradsson, Peter,Fraser-Reid, Bert
, p. 958 - 963 (2007/10/03)
Pent-4-enyl β-D-glucopyranoside and its peracetylated and perbenzylated derivatives are shown to be excellent substrates for preparation of a wide variety of spacer functionalities. The spacer derivatives so obtained are promising substrates for preparing agents such as neo-glycoconjugates, micelies, and liquid crystalline phases, which are of interest for studying various biological and physiological phenomena of carbohydrates.
Synthesis of detergent O-glucosides by reverse hydrolysis in alcohol- water biphasic systems using α- and β-glucosidases
Kosary, Judit,Stefanovits-Banyai,Boross
, p. 611 - 613 (2007/10/03)
The α- and β-glucosidases showed significant O-glycosylation activity with glucose as substrate and with different alcohols both as reaction partners and solvents in reverse hydrolytic processes. With native glucosidases upscaling resulted in low yields due to heterogeneity of reaction mixtures. Immobilization of the enzymes on a modified polyacrylamide-type bead support (Acrylex C-100) increased enzyme stability resulting in higher yields and permitted to perform glucosylations on a larger scale. From these experiments O-alkyl glucosides were isolated in moderate yields.
