Preparation method of S-alkyl-L-cysteine sulfoxide with high purity and high conversion rate

A technology of cysteine ​​sulfoxide and high conversion rate, which is applied in the field of preparation of high-purity and high-conversion S-alkyl-L-cysteine ​​sulfoxide, which can solve problems such as unstable applications and achieve simplified methods , save time, and achieve a single effect

Pending Publication Date: 2022-08-09
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Dialkylthiosulfinate has broad-spectrum antibacterial properties and is a potential natural antibacterial substance, but its application is limited due to its instability
However, the yield of the second step of this method is only 64%, and the overall yield is 64.64%, and this method needs to pass through argon and dry under reduced pressure. The two-step reaction takes more than 48 hours, and the preparation cost is still not low.

Method used

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  • Preparation method of S-alkyl-L-cysteine sulfoxide with high purity and high conversion rate
  • Preparation method of S-alkyl-L-cysteine sulfoxide with high purity and high conversion rate
  • Preparation method of S-alkyl-L-cysteine sulfoxide with high purity and high conversion rate

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Effect test

Embodiment 1

[0047] like figure 1 As shown, it is a flow chart of the first step of synthesizing S-alkyl-L-cysteine ​​sulfoxide in the present invention.

[0048] like figure 2 As shown, it is the flow chart of the second step in the synthesis of S-alkyl-L-cysteine ​​sulfoxide.

[0049] The steps for preparing S-allyl-L-cysteine ​​sulfoxide are:

[0050] Step 1: Mix 200ml of absolute ethanol and 40ml of deionized water in a beaker, then weigh 0.7mol of sodium hydroxide particles or 15ml of ammonia water, and then weigh 0.3mol of L-cysteine ​​after the rotor is fully stirred and dissolved. The solid was added to the system, and after it was completely dissolved, 0.6 mol of bromopropene was added and stirred for a while to obtain a transparent and clear pale yellow solution, which was sealed with a sealing film and continued to stir overnight for about 12 hours. Then adjust the pH of the solution to 5.5 with acetic acid. At this time, a large number of white crystals will be precipitated...

Embodiment 2

[0056] Self-made S-alkyl-L-cysteine ​​sulfoxide reacts with cysteine ​​sulfoxide lyase

[0057] Weigh 0.7 g of S-allyl-L-cysteine ​​sulfoxide and S-propyl-L-cysteine ​​sulfoxide respectively, and prepare 3 ml of deionized aqueous solution for each. Add 10 μl of cysteine ​​sulfoxide lyase and 20 μl of substrate to the 1 ml reaction system, react in a water bath at 37°C for 1 min, and use the DNPH method to detect the production of pyruvate to calculate the enzyme activity, such as Figure 4 Shown is the detection result of the reaction between the self-made S-alkyl-L-cysteine ​​sulfoxide and cysteine ​​sulfoxide lyase. It can be seen that the self-made S-alkyl-L-cysteine ​​sulfoxide can be cleaved by cysteine ​​sulfoxide lyase, indicating that the synthesized substance is correct.

Embodiment 3

[0059] HPLC-MS determination of self-made S-alkyl-L-cysteine ​​sulfoxide

[0060] Taking S-allyl-L-cysteine ​​sulfoxide as an example, it was configured into a 30% methanol aqueous solution of 0.5 mg / ml, and then sent to HPLC-MS for identification. The injection volume was 5 μl and the detection wavelength was 214 nm. , the chromatographic column is C18 column, the flow rate is 0.8ml / min, and the ion source is ESI positive ion. Mass spectrometry results such as Figure 5 shown is 177.22 for S-allyl-L-cysteine ​​sulfoxide and 178.22 for positive ion bombardment. It can be seen that the molecular weight is correct, the mass spectrometry result is a single peak, and the molecular weight of each position of this peak is 178.05 as the arrow moves, so the material purity is high.

[0061] The self-made S-propyl-L-cysteine ​​sulfoxide was also subjected to the above operations, and the HPLC-MS identification results were as follows Image 6 As shown, the molecular weight of S-prop...

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Abstract

The invention relates to the technical field of biological medicines, in particular to a preparation method of S-alkyl-L-cysteine sulfoxide with high purity and high conversion rate. Comprising a first step of substitution reaction and a second step of oxidation reaction, and the substitution reaction comprises the steps of alkaline substance dissolution, thioether substance solid dissolution and the like. The oxidation reaction comprises the following steps: dissolving in a hydrogen peroxide solution, carrying out cold ethanol precipitation and the like. S-alkyl-L-cysteine sulfoxide is a natural substrate of plant source cysteine sulfoxide lyase, dialkyl thiosulfinate is formed after the enzyme reacts with the substrate, and the product has broad-spectrum antibacterial performance and is a natural antibiotic. When the method is used for preparing the substrate S-alkyl-L-cysteine sulfoxide, the preparation time is greatly shortened, and the conversion rate is higher than that of the conventional method. According to HPLC-MS (High Performance Liquid Chromatography-Mass Spectrometry) detection, the prepared substrate S-alkyl-L-cysteine sulfoxide is correct in molecular weight, a peak pattern is a single peak, no obvious impure peak exists, and the purity is high.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a method for preparing S-alkyl-L-cysteine ​​sulfoxide with high purity and high conversion rate. Background technique [0002] Dialkylthiosulfinate has broad-spectrum antibacterial properties and is a potential natural antibacterial substance, but its unstable characteristics limit its application. It is produced after the bulbs of some Liliaceae plants are broken. The mechanism is that when the bulbs of Liliaceae plants are destroyed, the S-alkyl-L-cysteine ​​sulfoxide in the cytoplasm of the bulbs will interact with the cysteine ​​in the vacuole. Acid sulfoxide lyases contact each other to produce dialkylthiosulfinates. However, according to the survey results, the content of S-alkyl-L-cysteine ​​sulfoxide in the bulbs of Liliaceae plants in the natural state is very small, only 0.6-1% of its dry weight, and the extraction process is complicated and costly. , the existing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/48C07C315/02C07C319/14
CPCC07C315/02C07C319/14C07B2200/07C07C317/48C07C323/58
Inventor 杨春玉刘远翔
Owner SHANDONG UNIV
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