- Highly β-Selective Glycosylation Reactions for the Synthesis of ω-Functionalized Alkyl β-Maltoside as a Co-crystallizing Detergent
-
Abstract: Methods have been reported for the preparation of ω-functionalized alkyl maltoside and glycoside detergents via a simple and inexpensive synthetic route. The key step was stannic chloride-mediated glycosylation of long-chain alcohols or thiols with maltose octaacetate at 0 or –10°C, respectively, within a very short time (isolated yield 17–44%), which provided more than 98% β-selectivity.
- Elias, M.,Hossain, M. A.,Jamil, M. A. R.,Rahman, M. M.,Siddiki, S. M. A. Hakim
-
p. 1806 - 1814
(2020/12/01)
-
- Chemoenzymatic synthesis of β-D-glucosides using cellobiose phosphorylase from Clostridium thermocellum
-
Abstract Over the past decade, disaccharide phosphorylases have been successfully applied for the synthesis of numerous α-glucosides. In contrast, much less research has been done with respect to the production of β-glucosides. Although cellobiose phosphorylase was already successfully used for the synthesis of various disaccharides and branched trisaccharides, its glycosylation potential towards small organic compounds has not been explored to date. Unfortunately, disaccharide phosphorylases typically have a very low affinity for non-carbohydrate acceptors, which urges the addition of solvents. The ionic liquid AMMOENGTM 101 and ethyl acetate were identified as the most promising solvents, allowing the synthesis of various β-glucosides. Next to hexyl, heptyl, octyl, nonyl, decyl and undecyl β-D-glucopyranosides, also the formation of vanillyl 4-O-β-D-glucopyranoside, 2-phenylethyl β-D-glucopyranoside, β-citronellyl β-D-glucopyranoside and 1-O-β-D-glucopyranosyl hydroquinone was confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Moreover, the stability of cellobiose phosphorylase could be drastically improved by creating cross-linked enzyme aggregates, while the efficiency of the biocatalyst for the synthesis of octyl β-D-glucopyranoside was doubled by imprinting with octanol. The usefulness of the latter system was illustrated by performing three consecutive batch conversions with octanol imprinted cross-linked enzyme aggregates, yielding roughly 2 g of octyl β-D-glucopyranoside.
- De Winter, Karel,Van Renterghem, Lisa,Wuyts, Kathleen,Pelantová, Helena,K?en, Vladimír,Soetaert, Wim,Desmet, Tom
-
p. 1961 - 1969
(2015/06/02)
-
- 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.
- Wang, Qinqqin,Yu, Huilei,Zhao, Na,Li, Chunxiu,Shang, Yazhuo,Liu, Honglai,Xu, Jianhe
-
p. 275 - 280
(2016/04/10)
-
- 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.
- Wang, Qinqqin,Yu, Huilei,Zhao, Na,Li, Chunxiu,Shang, Yazhuo,Liu, Honglai,Xu, Jianhe
-
p. 275 - 280
(2012/06/29)
-
- POLYMER STABILIZER
-
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
-
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.
- Kino, Kuniki,Satake, Ryoko,Morimatsu, Takayuki,Kuratsu, Shoko,Shimizu, Yu,Sato, Masaru,Kirimura, Kohtaro
-
p. 2415 - 2417
(2008/12/23)
-
- A convenient stereoselective synthesis of β-D-glucopyranosides
-
The Koenigs-Knorr method plays a prominent role in the stereoselective synthesis of alkyl D-glucopyranosides via glycosidic linkage. Such an approach requires costly and toxic promoter salts of silver or mercury, which have additional separation problems. In a novel method a less toxic promoter salt like LiCO3 is used for glycosidation of several fatty alcohols including an aromatic alcohol. LiCO3 can be easily separated from the reaction mass and gives good yield.
- Joshi, Vishal Y.,Sawant, Manohar R.
-
p. 461 - 465
(2007/10/03)
-
- BF3 etherate-induced formation of C7-C 16-alkyl β-D-glucopyranosides
-
BF3 etherate-induced formation of C7-C 16-alkyl D-glucopyranosides is used as the key step in their synthesis from glucose and C7-C16-alkanols.
- Petrovic, Zorica,Konstantinovic, Stanimir,Spasojevic, Aleksandra
-
p. 132 - 134
(2007/10/03)
-
- Simple synthesis of β-D-glycopyranosides using β-glycosidase from almonds
-
Enzymatic glycosidation of twenty-one kinds of alcohols (n-hepanol, n-octanol, 2-phenylethanol, 3-phenylpropanol, 4-phenylbutanol, 5-phenylpentanol, 6-phenylhexanol, furfury alcohol, 2-pyridinemethanol, isobutanol, isopentanol, p-methoxycinnamylalcohol) including secondary alcohols (isopropanol, cyclohexanol, 1-phenylethanol) and 1, ω-alkanediols (1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol), salicyl alcohol and 4-nitrophenyl β-D-glucopyranoside (5) using β-glucosidase from almonds stereoselectively gave the corresponding β-D-glucopyranosides in moderate yield.
- Kurashima, Katsumi,Fujii, Mikio,Ida, Yoshiteru,Akita, Hiroyuki
-
p. 270 - 275
(2007/10/03)
-
- Synthesis of C7-C16-alkyl glycosides: Part I - Synthesis of alkyl D-glucopyranosides in the presence of tin (IV) chloride as a Lewis acid catalyst
-
The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivative (glucose) with fatty alkanols is used in a synthesis of C7-C16-alkyl glucopyranosides. The process occurs under the influence of tin (IV) chloride.
- Konstantinovic,Predojevic,Mojsilovic,Dimitrijevic,Milosevic
-
p. 796 - 801
(2007/10/03)
-
- Preparation of alkyl α- and β-D-glucopyranosides, thermotropic properties and X-ray analysis
-
Monohydrates of heptyl to decyl α-D-glucopyranosides as obtained from product mixtures of the Fischer glucosylation were crystallized from water at the Krafft point. The results of the single-crystal X-ray analysis of anhydrous α anomers and their monohydrates provide for a better understanding of crystal formation and stability of their hydrates. The preparation of alkyl β-D-glucopyranosides-without concomitant formation of α anomers as by-products-has been described. The thermotropic properties have been investigated for the α compounds and their monohydrates, and for the β-D-glucopyranosides. Copyright (C) 1998 Elsevier Science Ltd.
- Adasch, Volker,Hoffmann, Bettina,Milius, Wolfgang,Platz, Gerhard,Voss, Gundula
-
p. 177 - 187
(2007/10/03)
-