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Method for preparing ursodesoxycholic acid from hyodeoxycholic acid

A technology of hyodeoxycholic acid and ursodeoxycholic acid, which is applied in the field of biomedicine, can solve the problems of unfriendly environment, high safety risk, complicated process, etc., and achieve the goal of reducing production cost, reducing the pressure of safe production, and low coenzyme consumption Effect

Active Publication Date: 2021-07-20
泰安市炜创生物技术中心
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing technology, the technology from HDCA to UDCA is basically an all-chemical method, with complex process, high cost, unfriendly environment, and high safety risk. Therefore, it is necessary to develop a safer and easier production method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Preparation of ursodeoxycholic acid using hyodeoxycholic acid

[0026] (1) Add 22 g of chromium trioxide into 28 mL of concentrated sulfuric acid and dilute with water to 100 mL to obtain Jones reagent; dissolve 100 g of hyodeoxycholic acid in 1000 mL of acetone and treat with Jones reagent until a slight permanent orange color is obtained. After the mixture was allowed to stand for 10 min, a small amount of isopropanol was added to destroy excess oxidizing agent. The reaction mixture was filtered with diatomaceous earth, concentrated under reduced pressure to remove the solvent, and obtained 99.1 g of product R1, with a yield of 99.1%;

[0027] (2) Reaction system 500mL, add 400mL 0.05M pH 6.8 PBS buffer solution to 2L three-hole flask, then add 50g intermediate R1, 120g glucose, 40mL n-hexanol, 2.5mL Triton X-100, 0.1g NADP + , put the three-hole flask in a constant temperature water bath at 35°C, stir well and then adjust the pH to 6.8, then add 15g 3α-HSD...

Embodiment 2

[0029] Example 2 Preparation of ursodeoxycholic acid using hyodeoxycholic acid

[0030] (1) Add 22 g of chromium trioxide into 28 mL of concentrated sulfuric acid and dilute to 100 mL with water to obtain Jones reagent. 50 g of hyodeoxycholic acid was dissolved in 1000 mL of ethyl acetate and treated with Jones reagent until a slight permanent orange color was obtained. After the mixture was allowed to stand for 10 min, a small amount of isopropanol was added to destroy excess oxidizing agent. The reaction mixture was filtered with diatomaceous earth, and concentrated under reduced pressure to remove the solvent to obtain 48.8g of intermediate R1 with a yield of 97.6%;

[0031] (2) Reaction system 500mL, add 400mL 0.05M pH 7.0 PBS buffer into 2L three-hole flask, then add 25g intermediate R1, 50g glucose, 40mL n-hexanol, 2.5mL Triton X-100, 0.025g NAD + , put the three-hole flask in a constant temperature water bath at 37°C, stir well and adjust the pH to 7.0, then add 7.5g ...

Embodiment 3

[0033] Example 3 Preparation of ursodeoxycholic acid by using hyodeoxycholic acid

[0034] (1) Add 22 g of chromium trioxide into 28 mL of concentrated sulfuric acid and dilute to 100 mL with water to obtain Jones reagent. 100 g of hyodeoxycholic acid was dissolved in 1000 mL of acetone and treated with Jones reagent until a slight permanent orange color was obtained. After the mixture was allowed to stand for 10 min, a small amount of isopropanol was added to destroy excess oxidizing agent. The reaction mixture was filtered with diatomaceous earth, and concentrated under reduced pressure to remove the solvent to obtain 98.2g of product R1 with a yield of 98.2%;

[0035] (2) With a reaction system of 500mL, add 400mL of 0.05M pH 7.4 PBS buffer to a 2L three-hole flask, then add 75g of intermediate R1, 230g of glucose, 40mL of n-hexanol, 2.5mL of Triton X-100, and 0.3g of NADPH. The well flask was placed in a constant temperature water bath at 25°C, stirred evenly, and adjusted...

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Abstract

The invention provides a method for preparing ursodesoxycholic acid by using hyodeoxycholic acid, which comprises the following steps: firstly, oxidizing 3,6-hydroxyl of hyodeoxycholic acid into 3,6-keto by using a chemical method; secondly, reducing the 3-keto group into 3 alpha-hydroxyl by using 3[alpha]-steroid dehydrogenase, and adding hydroxyl to a substrate by using 7[beta]-hydroxylase to generate 7-hydroxyl; and finally, removing 6-keto by using a chemical method to generate UDCA. The chemical-enzyme method is simple in process, mild in reaction condition, environment-friendly, high in reaction substrate concentration and reproducible in coenzyme, the production cost and the environmental protection pressure are greatly reduced, and the chemical-enzyme method provides an environment-friendly, economical and efficient new thought for preparing the UDCA.

Description

technical field [0001] The invention belongs to the technical field of biomedicine and relates to a preparation method of ursodeoxycholic acid, in particular to a method for synthesizing ursodeoxycholic acid from hyodeoxycholic acid. Background technique [0002] Ursodeoxycholic acid (UDCA) is the main component of bear bile, and its chemical name is (3α, 7β)-dihydroxy-5βcholic acid. In medicine, it is used to increase the secretion of bile acid, change the composition of bile, reduce cholesterol and cholesterol lipid in bile, and help the cholesterol in gallstones dissolve gradually. It is used for the treatment of gallstones, cholestatic liver disease, fatty liver, and various types of hepatitis. , toxic liver disorders, cholecystitis, cholangitis and biliary dyspepsia, bile reflux gastritis, eye diseases, etc. Since the 1980s, when ursodeoxycholic acid was found to effectively dissolve cholesterol gallstones, new researches have shown that ursodeoxycholic acid has a posi...

Claims

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Application Information

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IPC IPC(8): C07J9/00C12P33/06
CPCC07J9/005C12P33/06Y02A50/30
Inventor 周炜强
Owner 泰安市炜创生物技术中心
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