Method for preparing D-asparagine and D-homoserine

A technology of homoserine and asparagine, which is applied in the preparation of cyanide reaction, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of high cost, long route, unsuitable for large-scale production, etc., and achieves environmental pollution. The effect of small size, simple process and low production cost

Inactive Publication Date: 2008-12-31
SOUTHEAST UNIV
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  • Abstract
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Problems solved by technology

[0007] The known methods for preparing D-homoserine are either splitting expensive DL-homoserine as a raw material, or preparing expensive D-methionine as a raw material through multi-step reactions. The raw materials are not easy to obtain, the cost is high, and the route is long. Not suitable for large-scale production

Method used

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  • Method for preparing D-asparagine and D-homoserine
  • Method for preparing D-asparagine and D-homoserine
  • Method for preparing D-asparagine and D-homoserine

Examples

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Effect test

Embodiment 1

[0045]Take 15g of DL-aspartic acid-β-methyl ester into a three-necked flask, add 50-100mL of water, raise the temperature to 40-95°C, and add L-dibenzoyl tartaric acid (L-DBTA, 18.8g) into it The methanol solution was cooled to room temperature after reacting for 1 hour, and filtered to obtain 21.7 g of D-aspartic acid-β-methyl ester·L-DBTA, with a yield of 86%.

Embodiment 2

[0047] Take 30g of D-aspartic acid-β-methyl L-DBTA, put it in a 250mL three-neck bottle, add 30-150mL of ethanol and 17mL of triethylamine, stir and react at room temperature for 2-4 hours, filter to obtain a white powder Solid D-aspartic acid methyl ester 6.58g, yield 74.8%.

Embodiment 3

[0049] Add 10g of D-aspartic acid-β-methyl ester and 50-300mL of methanol into the three-neck flask, stir well and then feed NH 3 Gas, the temperature is controlled at -5 ~ 15 ° C for 1-3 hours, after rising to room temperature, continue to feed NH 3 Gas for 2 to 3 hours, stand in a water bath at 30°C for 48 hours, then concentrate to dryness under reduced pressure; dissolve the residue in 30ml of distilled water, add 150ml of methanol to precipitate, freeze and crystallize, and filter to obtain 4.8g of D-asparagine . Dissolve 4.g of crude D-asparagine in hot distilled water, add a small amount of activated carbon for decolorization, add 150ml of methanol under stirring, and filter to obtain 4.1g of white orthorhombic crystalline D-asparagine, with a total yield of 49.9%.

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Abstract

A preparation method for D-asparagine and D-homoserine comprises the following steps: a, DL-aspartic acid methyl ester is taken as raw material, L-DBTA as resolving agent, water as solvent to carry through resolution reaction for 0.5-5 hours at 40-95 DEG C so as to get D-aspartic acid methyl ester-L-DBTA salt; b, the D-aspartic acid methyl ester-L-DBTA salt is stirred and hydrolyzed for 2-4 hours at room temperature in the presence of alkali to get D-aspartate-beta-methyl ester; c, the D-aspartate-beta-methyl ester is ammonolyzed in a solvent with ammonia gas, ammonia or liquid ammonia to get the D-asparagine; d, the D-aspartate-beta-methyl ester is deoxidized with reductant for 1-10 hours at 0-80 DEG C, neutralized with acid and then concentrated and processed through hydrogen or sodium cation exchange resin to get the D-homoserine. The invention provides a technology which uses cheap DL-aspartate to prepare D-asparagine and D-homoserine through esterification, resolving, ammonolysis, deoxidizing and other processes, thereby laying a solid foundation for the industrial production of two important D-type amino acids.

Description

technical field [0001] The invention is a method for preparing D-type amino acid, which belongs to the technical field of preparation of chiral organic compounds. Background technique [0002] Both D-asparagine and D-homoserine are important chiral amino acids, which are mainly used in the fields of chiral reagents and chiral drug synthesis. Oxytocin prepared from D-asparagine has good oxytocin and blood pressure lowering effects; D-homoasparagine prepared from D-asparagine is also an important drug intermediate, and the β-peptide synthesized from it has Nanotube structure, resistant to enzymatic degradation, has high medicinal potential [1] . M. Hashimoto [2] prepared Nocardin Baccidin A from D-homoserine; the protease inhibitor prepared from D-homoserine can effectively inhibit protease and prevent protein hydrolysis [3] ; In addition, it is an important raw material for the synthesis of antifungal peptides [4] , and for the preparation of other pharmaceutical interme...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/12C07C231/20C07C229/22C07C227/16
Inventor 蒋立建韩冲李琼瑶夏爱华
Owner SOUTHEAST UNIV
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