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A kind of preparation method of d-arginine hydrochloride

A technology of arginine hydrochloride and arginine, which is applied in the field of preparation of D-arginine hydrochloride, can solve the problems of low yield, low product yield, high cost, etc., and achieve high yield and high preparation The method is simple and the effect is convenient to produce

Active Publication Date: 2018-08-17
CHENGDU BAISHIXING SCI & TECH IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The easiest way is the chemical resolution of the racemate, because this method does not require multi-step reactions, the reaction conditions are easy to control, and there is no need to change other forms of amino acid lipids (that is, it is not necessary to protect the functional group to change the amino acid). nature, to obtain the purpose of resolution), but the yield of this method is quite low-cost and high, it is not suitable for industrial production, the product yield is low, and the chiral content does not meet the quality requirements of chiral compounds, so the application of this method is limited

Method used

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  • A kind of preparation method of d-arginine hydrochloride

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: a kind of preparation method of D-arginine hydrochloride, it comprises the following steps:

[0025] S1. Racemization: the purity is greater than 97% and L-arginine hydrochloride is dissolved in glacial acetic acid, adding catalyst salicylaldehyde, and the weight ratio of L-arginine hydrochloride, glacial acetic acid and salicylaldehyde is 1: 4:0.1, reflux at 95°C for 6 hours to obtain DL-arginine hydrochloride;

[0026] S2. Acetylation: Dissolve DL-arginine hydrochloride in sodium hydroxide and add acetic anhydride dropwise. The weight ratio of DL-arginine hydrochloride, sodium hydroxide and acetic anhydride is 1:4 : 0.5, reacted for 1.5h, cooled and crystallized, and the gained solid was AC-DL-arginine;

[0027] S3. Enzymolysis: add acylase to AC-DL-arginine, adjust the pH value to 8 with 10% sodium hydroxide, and the weight ratio of AC-DL-arginine to acylase is 1:0.02,35 Incubate at ℃ for 40 hours to obtain D-arginine hydrochloride;

[0028] S4. Refi...

Embodiment 2

[0029] Embodiment 2: a kind of preparation method of D-arginine hydrochloride, it comprises the following steps:

[0030] S1. Racemization: the purity is greater than 97% and L-arginine hydrochloride is dissolved in glacial acetic acid, adding catalyst salicylaldehyde, and the weight ratio of L-arginine hydrochloride, glacial acetic acid and salicylaldehyde is 1: 7:0.2, reflux at 105°C for 8 hours to obtain DL-arginine hydrochloride;

[0031] S2. Acetylation: Dissolve DL-arginine hydrochloride in sodium hydroxide, drop acetic anhydride, the weight ratio of DL-arginine hydrochloride, sodium hydroxide and acetic anhydride is 1:5 : 1, reacted for 3h, cooled and crystallized, and the gained solid was AC-DL-arginine;

[0032] S3. Enzymolysis: add acylase to AC-DL-arginine, adjust the pH value to 9 with 10% sodium hydroxide, and the weight ratio of AC-DL-arginine to acylase is 1:0.05, 40 Incubate at ℃ for 48 hours to obtain D-arginine hydrochloride;

[0033] S4. Refining: heat th...

Embodiment 3

[0034] Embodiment 3: a kind of preparation method of D-arginine hydrochloride, it comprises the following steps:

[0035] S1. Racemization: the purity is greater than 97% and L-arginine hydrochloride is dissolved in glacial acetic acid, adding catalyst salicylaldehyde, and the weight ratio of L-arginine hydrochloride, glacial acetic acid and salicylaldehyde is 1: 5:0.15, reflux at 100°C for 7 hours to obtain DL-arginine hydrochloride;

[0036] S2. Acetylation: Dissolve DL-arginine hydrochloride in sodium hydroxide and add acetic anhydride dropwise. The weight ratio of DL-arginine hydrochloride, sodium hydroxide and acetic anhydride is 1:4.3 : 0.8, reacted 2h, cooled and crystallized, and the gained solid was AC-DL-arginine;

[0037] S3. Enzymolysis: add acylase to AC-DL-arginine, adjust the pH value to 8- with 10% sodium hydroxide, the weight ratio of AC-DL-arginine to acylase is 1:0.03, Incubate at 37°C for 42 hours to obtain D-arginine hydrochloride;

[0038] S4. Refining...

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Abstract

The invention discloses a preparation method of D-arginine monohydrochloride. The preparation method comprises the following steps: S1, racemization, namely, dissolving L-arginine monohydrochloride into glacial acetic acid, and adding a catalyst into the obtained solution for carrying out racemization reaction, as to as obtain DL-arginine monohydrochloride; S2, acetylation, namely, dissolving DL-arginine monohydrochloride into sodium hydroxide, dropwise adding acetic anhydride, and carrying out acetylation reaction to obtain solid, which is AC-DL-arginine; and S3, enzymolysis, namely, adding acylase into the AC-DL-arginine, and carrying out enzymolysis to prepare D-arginine monohydrochloride. According to the preparation method, L-arginine monohydrochloride is adopted as the raw material, D-arginine monohydrochloride is prepared through racemization, acetylation and enzymolysis, and a novel efficient preparation method is provided for the preparation of D-arginine monohydrochloride; D-arginine monohydrochloride prepared by the preparation method provided by the invention is high in yield, the EE value can achieve 99.7%; and the preparation method is simple, convenient, pollution-free and environmentally friendly, and suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a preparation method of D-arginine hydrochloride. Background technique [0002] D-arginine hydrochloride, Cas: 627-75-8, molecular formula: C 6 h 15 ClN 4 o 2 , Molecular weight: 210.66, molecular structural formula such as (I), [0003] [0004] Properties: white crystalline powder, melting point: 216-218℃, specific rotation: -21º; (C=3.51NHCl), colorless crystalline substance; odorless, sweet; soluble in water, insoluble in ethanol, ether and chloroform ;The decomposition point is 251-253°C. If one or several L-type amino acids in the short peptide are replaced with D-type amino acids, the biological functions or characteristics of the new short peptide are very different from those of the original short peptide; Antibiotics are mixed with D-type amino acids, which are difficult to be degraded by bacterial enzymes and will not produce drug resistance; D-argi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P13/10C07C279/14C07C277/08
Inventor 王刚
Owner CHENGDU BAISHIXING SCI & TECH IND
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