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Preparation method of D-asparagine

A technology of asparagine and aspartic acid, which is applied in the field of chemical biology, can solve the problems of difficult to obtain D-asparagine and L-asparagine α-decarboxylase activity, etc., and achieve abundant raw material sources and suitable Large-scale production, the effect of expanding the range of raw materials

Inactive Publication Date: 2011-10-26
SHANDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At first, I tried to use L-asparagine α-decarboxylase in microorganisms to convert the L-type enantiomer in DL-asparagine, and separate and prepare D-asparagine. As a result, it was found that L-asparagine α in various microorganisms - The activity of decarboxylase is very low, it is difficult to obtain D-asparagine by this method

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1) Mix 148 grams of phthalic anhydride with 133 grams of L-aspartic acid, heat up to 155°C, react for 50 minutes, add 1000 ml of water to dissolve, cool and precipitate crystals; filter and dry to obtain 252 grams of phthaloyl- L-aspartic acid;

[0031] 2) The sodium salt of 252 grams of phthaloyl-L-aspartic acid and 0.5 grams of phthalimide was added to 300 milliliters of acetic anhydride, refluxed for 30 minutes, cooled and crystallized, filtered and dried to obtain ortho Phthaloyl-DL-aspartic anhydride 226 grams;

[0032] 3) Add 122.5 grams of phthaloyl-DL-aspartic anhydride to 200 milliliters of tetrahydrofuran ammonia solution containing 5% ammonia, react at room temperature for 2 hours, evaporate and recover tetrahydrofuran, add 600 milliliters of water to the solid, and use 6M Adjust the pH value to 9 with sodium hydroxide solution to dissolve all the solids, then adjust the pH value to 3 with 6M hydrochloric acid, re-precipitate the solid product, filter and dr...

Embodiment 2

[0036] 1) Mix 178 grams of phthalic anhydride with 133 grams of L-aspartic acid, heat up to 180 ° C, react for 20 minutes, add 1000 ml of water to dissolve, decolorize activated carbon, cool and precipitate crystals; filter and dry to obtain 255 grams of o-phthalic acid Diformyl-L-aspartic acid;

[0037] 2) Add 255 grams of phthalyl-L-aspartic acid and 1.0 gram of sodium acetate to 300 ml of acetic anhydride, reflux for 20 minutes, cool and crystallize, filter and dry to obtain phthalyl-DL-day 220 grams of aspartic anhydride;

[0038] 3) Add 122.5 grams of phthaloyl-DL-aspartic anhydride to 300 milliliters of 10% ammonia-containing tetrahydrofuran ammonia solution, react at room temperature for 2 hours, evaporate and recover tetrahydrofuran, add 600 milliliters of water to the solid, and use hydrogen Adjust the pH value of the sodium oxide solution to 9 to dissolve all the solids, and then adjust the pH value to 3 with 6M hydrochloric acid to re-precipitate the solid product,...

Embodiment 3

[0042] 1) Mix 120 grams of phthalic anhydride and 133 grams of L-aspartic acid, heat up to 130 ° C, react for 60 minutes, add 1000 ml of water to dissolve, cool and precipitate crystals; filter and dry to obtain 180 grams of phthaloyl- L-aspartic acid;

[0043] 2) The sodium salt of 180 grams of phthaloyl-L-aspartic acid and 0.5 grams of phthalimide was added to 300 milliliters of acetic anhydride, refluxed for 60 minutes, cooled and crystallized, filtered and dried to obtain ortho Phthaloyl-DL-aspartic anhydride 162 grams;

[0044] 3) Add 122.5 grams of phthaloyl-DL-aspartic anhydride to 300 milliliters of tetrahydrofuran ammonia solution containing 4% ammonia, react at room temperature for 2 hours, evaporate and recover tetrahydrofuran, add 600 milliliters of water to the solid and oxidize it with hydrogen Adjust the pH value of the sodium solution to 9 to dissolve all the solids, then adjust the pH value to 3 with 6M hydrochloric acid, re-precipitate the solid product, fil...

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Abstract

The invention discloses a preparation method of D-asparagine, which is characterized in that the method comprises the following steps: (1) allowing L-asparagine to react with phthalic anhydride at 130 DEG C-180 DEG C so as to generate phthaloyl-L-aspartic acid; (2) allowing the phthaloyl-L- asparagine obtained in step (1) to perform reflux reaction with acetic anhydride and a racemization reagentfor 20-60 min so as to generate phthaloyl-DL-aspartic anhydride; (3) allowing the phthaloyl-DL- aspartic anhydride obtained in step (2) to react with an ammonia tetrahydrofuran solution so as to obtain phthaloyl-DL-asparagine; (4) allowing the phthaloyl-DL-asparagine obtained in step (3) to react with hydrazine hydrate to remove the phthaloyl group so as to obtain the product of DL-asparagine; (5) specifically hydrolyzing L-asparagine in the DL-asparagine obtained in step (4) by microbial L-asparaginase for separation so as to obtain D-asparagine and L-asparagine.

Description

technical field [0001] The invention relates to a preparation method of D-asparagine, which belongs to the field of chemical biology. Background technique [0002] D-Asparagine is an important drug synthesis intermediate, which can be used to prepare oxytocin with good oxytocin and blood pressure lowering properties, and can also be used as an important drug intermediate β-Homo-Asparagine raw material. In addition, D-asparagine is also commonly used in pharmacological research. Studies have shown that it has a significant inhibitory effect on mouse cough induced by atomized ammonia stimulation and guinea pig asthma induced by acetylcholine and histamine. It can also be used to treat bronchitis . [0003] There are few literature reports on the synthesis method of D-asparagine. Some domestic scholars (Chinese patent 200810020843.2) use DL-aspartic acid methyl ester as raw material to obtain D-aspartic acid-β-methyl ester through chemical resolution; Then, D-aspartic acid-β-...

Claims

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Application Information

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IPC IPC(8): C12P13/20
Inventor 钱绍松陈月虎崔洪友
Owner SHANDONG UNIV OF TECH
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