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Method for catalytic synthesis of phenylallyl beta-D-glucoside from magnetic cross-linked enzyme aggregates

A technology of glucoside and cross-linking enzyme, which is applied in the field of biocatalysis, can solve the problems of high cost and achieve the effects of high added value, novel invention content and improved use efficiency

Active Publication Date: 2015-04-29
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although chemical methods can also synthesize phenylpropenyl β-D-glucoside, most require selective protection, activation and expensive production equipment and catalysts

Method used

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  • Method for catalytic synthesis of phenylallyl beta-D-glucoside from magnetic cross-linked enzyme aggregates
  • Method for catalytic synthesis of phenylallyl beta-D-glucoside from magnetic cross-linked enzyme aggregates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of magnetically cross-linked β-glucosidase aggregates M-CLGAs:

[0032](1) Mix 1.351 g FeCl3, 0.685 g FeSO4 7H2O and 25 mL of deionized water at room temperature, add ammonia water until the precipitation does not increase, wash with deionized water after several centrifuges until the pH value is 7.0, and bake at 90 °C Dry for 2 h to obtain unsilanized magnetic iron oxide particles. Take 0.02 g of the above-mentioned dried and unsilanized magnetic iron oxide particles, add 2.5 mL of methanol, 100 μL of 3-aminopropyltriethoxysilane, and 25 μL of deionized water, mix well, ultrasonicate for 30 min, and then add 1.5 mL of glycerol was shaken vigorously at 90 °C for 6 h, the mixture was centrifuged and then dried at 100 °C to obtain stable silanized magnetic iron oxide particles.

[0033] (2) Add 1 mL of 2 mg / mL β-glucosidase enzyme solution prepared with pH 5.0 citric acid-phosphate buffer solution and a certain amount of magnetic iron oxide particles into a 5...

Embodiment 2

[0035] Add 100 mg of D-glucose, 220 mg of phenylpropenyl alcohol, 1.6 mL of 1,4-dioxane, and 0.4 mL of citric acid-phosphate buffer solution with a pH of 5.5 in a 10 mL ground-mouth Erlenmeyer flask to make the entire reaction system The total volume is 2 mL. Place the flask in a constant temperature water bath at 50°C and shake it well for 10 minutes, then immediately add 15 U / mL of magnetically cross-linked β-glucosidase aggregates into the flask to initiate the reaction, and cover with a rubber stopper. Finally, the flask was placed in a constant temperature shaking incubator to react at 50°C and 250rpm for 72h.

[0036] After the reaction, 100 μL was sampled, 1.9 mL of acetonitrile was added to dilute the reaction solution and ultrasonically oscillated for 20 min, centrifuged at 10,000 rpm for 5 min, the supernatant was filtered with a 0.45 μm filter membrane, and the product phenylpropenyl β-D- Glucoside was detected, and HPLC detection conditions: Waters 2996 UV detecto...

Embodiment 3

[0038] Add 100 mg of D-glucose and 120 mg of phenylpropenyl alcohol to a 10 mL conical flask, then add 1.4 mL of 1,4-dioxane, and 0.6 mL of citric acid-phosphate buffer solution with a pH of 5.5 to make the entire reaction system The total volume is 2 mL. Place the flask in a constant temperature water bath at 50°C and shake it well for 10 minutes, then immediately add 15 U / mL of magnetically cross-linked β-glucosidase aggregates into the flask to initiate the reaction, and cover with a rubber stopper. Finally, the flask was placed in a constant temperature shaking incubator to react at 50°C and 250rpm for 72h.

[0039] The product phenylpropenyl β-D-glucoside was detected by the same detection method as in Example 2, and the product concentration could reach 1.92 g / L.

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Abstract

The invention provides a method for catalytic synthesis of phenylallyl beta-D-glucoside from magnetic cross-linked enzyme aggregates and belongs to the field of biocatalysis. A substrate phenylallyl alcohol and D-glucose are subjected to glycosylation in the presence of an enzyme to synthesize phenylallyl beta-D-glucoside and a reaction system is a non-aqueous-phase system. A report on catalytic glycosylation synthesis of phenylallyl beta-D-glucoside by utilizing magnetic cross-linked beta-glucosidase aggregates is not seen, the method disclosed by the invention has unique and innovative independent innovation and in the non-aqueous-phase system, the activity and stability of the enzyme can be ensured and the thermodynamic equilibrium moves towards the hydrolysis reaction direction. The system is simple, phenylallyl beta-D-glucoside can be directly synthesized in one step and products are easily separated and purified so that high purity is achieved. The substrate selected in the reaction is an inexpensive chemical raw material, the cost is significantly saved compared to the traditional method for extracting phenylallyl beta-D-glucoside from Rhodiola plants and the phenylallyl beta-D-glucoside is suitable for industrial production.

Description

technical field [0001] The invention specifically relates to a method for catalyzing and synthesizing phenylpropenyl β-D-glucoside by a magnetic cross-linking enzyme aggregate, and belongs to the field of biocatalysis. Background technique [0002] Phenylpropenyl β-D-glucoside, also known as Rosin, is an active ingredient with a very low content in the extract of the traditional Chinese medicine Rhodiola rosea. Rhodiola is a perennial herb or subshrub belonging to the Sedum family Rhodiola. It has been used in traditional Chinese herbal medicines and has a variety of physiological activities. The main component of Rhodiola extract is salidroside. However, studies in recent years have shown that phenylpropenyl β-D-glucoside also has functions such as anti-fatigue, anti-aging, anti-oxidation, anti-tumor, and enhancing immunity, which makes phenylpropenyl β-D-glucoside also receive attention of the pharmaceutical community. Not all Rhodiola plants contain phenylpropenyl β-D-g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/44
Inventor 石贤爱王祖鑫陈荫楠吴星涛
Owner FUZHOU UNIV
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