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A kind of method utilizing hyodeoxycholic acid to prepare ursodeoxycholic 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., so as to reduce the production cost, reduce the safety production pressure, and reduce the consumption of coenzyme. Effect

Active Publication Date: 2022-08-09
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 to 28 mL of concentrated sulfuric acid, dilute to 100 mL with water 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 allowing the mixture to stand for 10 min, a small amount of isopropanol was added to destroy the excess oxidant. The reaction mixture was filtered with celite, and concentrated under reduced pressure to remove the solvent to obtain 99.1 g of product R1 with a yield of 99.1%;

[0027] (2) 500mL reaction system, add 400mL 0.05M pH 6.8 PBS buffer to a 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 evenly and adjust the pH to 6.8, then add 15g 3α-HSDH, 25g 7β-hydroxylase, 10g GDH, kee...

Embodiment 2

[0029] Example 2 Using hyodeoxycholic acid to prepare ursodeoxycholic acid

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

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

Embodiment 3

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

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

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

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Abstract

The invention provides a method for preparing ursodeoxycholic acid by using hyodeoxycholic acid. First, the 3,6-hydroxyl group of hyodeoxycholic acid is oxidized to 3,6-ketone group by chemical method; the second step is using 3α-steroid. Dehydrogenase reduces the 3-keto group to 3α-hydroxyl, and uses 7β-hydroxylase to add hydroxyl to the substrate to generate 7-hydroxyl; finally, chemically removes the 6-keto group to generate UDCA. The chemical-enzymatic process is simple, the reaction conditions are mild, the environment is friendly, the reaction substrate concentration is high, and the coenzyme can be regenerated, which greatly reduces the production cost and environmental protection pressure. The chemical-enzymatic preparation of UDCA provides an environmentally friendly, economical and efficient method new ideas.

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-5β cholanoic acid. In medicine, it is used to increase the secretion of bile acids, change the composition of bile, reduce cholesterol and cholesterol lipids in bile, and facilitate the gradual dissolution of cholesterol in gallstones. It is used to treat gallstones, cholestatic liver disease, fatty liver, and various types of hepatitis. , toxic liver disorder, cholecystitis, cholangitis and biliary dyspepsia, bile reflux gastritis, eye diseases, etc. Since ursodeoxycholic acid was found to be effective in dissolving cholesterol stones in the 1980s, new studies have shown that ursodeoxycholic acid has a posit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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