5391-18-4Relevant articles and documents
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
Wang, Feng,Huang, Dengfa,Ma, Yong,Zhang, Fuming,Linhardt, Robert J.
, p. 246 - 260 (2019/02/03)
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
Farrell, Mark P.,Doyle, Lisa M.,Murphy, Paul V.
supporting information, p. 2726 - 2731 (2018/06/20)
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.
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.
