JPS63214188A - Production of amino acid decarboxylation product and apparatus therefor - Google Patents

Abstract

PURPOSE:To obtain an amino acid decarboxylation product useful as medicines in high purity and concentration, by adding immobilized amino acid decarboxylate to a raw material amino acid and reacting both within a suitable action pH region. CONSTITUTION:Immobilized particles of amino acid decarboxylase are introduced into a reaction vessel 5 and held therein and a raw material solution 1 of an amino acid, such as dibasic amino acid, is added through a raw material transfer pipe 3 and reacted until the pH attains <=6.5 which is an enzymic suitable action pH range. The raw material is successively added so as to attain the total concentration of a monobasic acid which is a reaction product substance and raw material amino acids attains >=1wt.%. A slurry of the raw material amino acid in a concentration corresponding to the concentration of the product substance is then fed by a raw material transfer pump 4 drivably connected to a pH sensor 8 and pH automatic regulator 9 and a reaction solution 6 in an equal volume is taken out by a reaction solution transfer pipe 10 to carry out continuous operation. The resultant reaction solution is subsequently passed through a reaction solution concentrator 11 and dryer 13 to recover a monobasic amino acid which is a dried product 15.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method and apparatus for producing amino acid decarboxylated products, and in particular to a method and apparatus for producing decarboxylated products from a substrate amino acid using an immobilized amino acid decarboxylase. The present invention relates to a suitable manufacturing method and manufacturing apparatus.

[Conventional technology]

Decarboxylation products of amino acids, such as T-aminobutyric acid, are used medicinally and are currently produced by chemical synthesis methods.

The present inventors conducted research with the aim of inventing a highly practical production method that utilizes an enzymatic reaction, that is, a production method that can obtain a reaction solution containing a highly concentrated and highly purified decarboxylation product.

The existence of amino acid decarboxylation reactions by enzymes is already known, and several enzymes corresponding to each reaction have been isolated from plants and microorganisms. These are discussed in Journal Biological Chemistry, Volume 206 (1).
954) p215-219. Journal Biological Chemistry, Volume 235 (1960)
p1649-1652. Journal Biological
Chemistry, Volume 235 (1960) p1653~
1657. Biochemical Journal, Volume 62.

p301-303 (Journal Biology
cal Chemistry+206°p215.19
54+ p215-219. Journal B
iological chemistry, 235. ,1
960, p1649-1652. JournalBi
Logical Chemistry+ 235. +
1960, p1653-1657, Bioch
chemical Journal, 62. p301(1
956)).

[Problem that the invention seeks to solve]

However, these enzymes have a narrow operating pH range, and the decarboxylated products have extremely high solubility in water, are hygroscopic, and are difficult to crystallize. Furthermore, known methods are carried out only at dilute substrate concentrations and in the presence of pH buffers, and require extensive concentration operations and the use of pH buffers and neutralizing agents after the reaction, similar to chemical synthesis methods. It is necessary to remove and separate and purify the product.

The present inventors contacted the enzyme in solution with a highly concentrated substrate solution in the presence of a buffer or without the addition of a neutralizing agent,
A decarboxylation reaction was attempted. However, under the above conditions, the enzyme is subject to high concentration substrate inhibition and the pH at the start of the reaction is not in the preferred pH range, so the enzyme is inactivated and the reaction rate is reduced, as shown in Figure 1. It was found that it was difficult to react efficiently.

[Means for solving problems]

Therefore, the present inventors conducted extensive research on a method for obtaining a highly concentrated solution of decarboxylated amino acids without adding a pH buffer or a neutralizing agent.

As a result, by immobilizing amino acid decarboxylase, the above-mentioned high-concentration substrate inhibition effect is reduced, and even if the reaction pH deviates to some extent from the preferred range, it is difficult to deactivate, and the pH
It was found that the stability increased (Figure 2). Using a free enzyme that is not immobilized, as shown in Figure 3, without adding a buffer or neutralizing agent, the raw amino acid was adjusted to the appropriate pH range while monitoring the pH change of the reaction solution as the reaction progressed. If it is supplied semi-continuously, the reaction can be continued for a certain period of time. However, changes in pH eventually deactivate the enzyme and stop the reaction. However, it has been found that by using an immobilized enzyme that is more stable against pH changes, the reaction can be carried out continuously as shown in FIG. 4.

The present invention was completed as a result of further research based on the above-mentioned novel findings, and the first invention is the invention of a method for producing an amino acid decarboxylation product. In producing a decarboxylated product of the amino acid by allowing the immobilized amino acid decarboxylase to act on the amino acid in a reaction solution, the raw material amino acid is used in a reaction pH range of the reaction solution suitable for the action of the immobilized amino acid decarboxylase. The second invention is characterized in that the reaction solution is supplied in excess or insufficient amount so that the amino acid decarboxylation product is maintained at , an invention of an apparatus for producing an amino acid decarboxylation product, which includes: a mixing mechanism for a reaction solution in a reaction tank; and a pH for detecting the pH of the reaction solution in the reaction tank.
a detection device, a pH adjustment device that can set pH in conjunction with the pH detection device, a raw material amino acid supply mechanism that supplies a required amount of raw amino acid to the reaction tank in conjunction with the pH adjustment device, and This system is characterized by having a particle trapping mechanism that prevents the outflow of chemical particles, and a mechanism that extracts only the reaction liquid to the outside of the tank.

Hereinafter, the content of the present invention will be explained in more detail.

The type of enzymatic reaction that can be applied to the present invention is not particularly limited as long as it is a decarboxylation reaction of dibasic amino acids. For example, the corresponding 1 from glutamic acid, aspartic acid, etc.
This is a decarboxylation reaction that produces carbon dioxide gas originating from basic amino acids and the carboxyl group at the α-position.

The origin of the enzyme used in the present invention is not particularly limited. For example, as the glutamic acid decarboxylase, enzymes originating from microorganisms such as Escherichia coli or enzymes originating from plants such as Kapocha can be used.

The immobilization method is also not particularly limited. For example, conventionally known methods such as a covalent bonding method using glutaraldehyde and a gel entrapment method using polyacrylamide gel are also fully applicable.

A free dibasic amino acid is used as a raw material amino acid as a substrate. The form of the amino acid may be a solid such as a crystal, a slurry in which a solid is dispersed, or a concentrated solution.

However, it is preferable that the slurry and liquid be as thick as possible, preferably 1% or more.

By maintaining the total concentration of the raw material amino acid and the reaction product in the reaction solution at a high concentration of 1% or more, the reaction product can be easily separated.

The pH is appropriately selected depending on the reaction, that is, the characteristics of the enzyme used. Generally, the preferred pH for the decarboxylation reaction is 6 or less.

The reaction temperature is also appropriately selected depending on the thermal stability of the corresponding enzyme. This can usually be carried out at a temperature of 30°C or higher.

If the temperature is below 30°C, the reaction rate is low and it is not practical.

The method for detecting the reaction pH is also not particularly limited, and conventionally known methods may be used. For example, detection is performed using a pH electrode.

As for the reaction type, a fluidized bed type is suitable because carbon dioxide gas is generated as the reaction progresses and the pH of the reaction solution can be uniformly adjusted.

[For production]

Since the present invention uses an enzyme in which decarboxylase is immobilized as a reaction catalyst, it is possible to prevent or reduce high concentration substrate inhibition, and the enzyme is inactivated even if the reaction pH deviates from the preferred range to some extent. It becomes difficult to do.

Furthermore, the present invention detects the pH in the reaction solution and detects the pH during the reaction.
Adjust the reaction pH by adding as much raw amino acid as possible to the optimal pH range for the immobilized enzyme without adding a neutralizing agent to the H mild buffer, by adding only the raw amino acid as the substrate. After the reaction, the pH
The reaction product can be obtained without removing the 1l buffer or neutralizing agent.

〔Example〕

First, a specific process flow of the present invention will be explained based on a schematic diagram of an embodiment of the apparatus for producing an amino acid decarboxylation product of the present invention.

In FIG. 5, a raw material liquid 1, ie, a dibasic amino acid solution or slurry, is supplied from a raw material liquid storage tank 2 to a reaction tank 5 via a raw material liquid transfer pipe 3 by a raw material liquid transfer pump 4. Inside the reaction tank 5, a fluidized bed is formed in which immobilized particles on which an enzyme corresponding to the desired decarboxylation reaction is immobilized are suspended in the reaction liquid. The driving force for fluidization may be aeration, for example, by circulating carbon dioxide gas produced by the reaction, or by mechanical stirring. The pH of the reaction solution 6 is detected by a pH detection device 8,
The signal is transmitted to the pH automatic adjustment device 9. In the automatic pH adjustment device, one or both of an upper limit value and a lower limit value for turning off the raw material transfer pump 4 so as to reach the optimum pH for the reaction is set in advance. As the reaction progresses, the pH of the reaction solution changes and when it deviates from the optimum range, the pH automatic adjustment system described above will supply the raw material solution in just the right amount.The carbon dioxide gas generated during the reaction will be replaced by the produced carbon dioxide. Gas is discharged from the reaction tank through a gas discharge pipe 7.

The reaction solution 6 containing the produced monobasic amino acid is transferred to the concentration bag fil via the reaction solution transfer pipe IO and concentrated.

The concentrated reaction liquid further passes through a concentrated reaction liquid transfer pipe 12, is dried by a drying device 13, and is extracted out of the system as a dry product 15 via a dry product transfer pipe 14.

In addition, in order to increase the purity of the product, as shown in the flowchart of FIG. 6, unreacted raw material amino acid crystals that are precipitated when the reaction solution 6 is concentrated in the tM condensation device 11 are removed in the solid-liquid separation device 16, It is also possible to dry only the mother liquor containing the reaction product using the drying device 13.

Furthermore, as shown in FIG. 7, the reaction solution can be concentrated in a concentrator 11 and then cooled in a cooling device 20 to more efficiently remove unreacted amino acid crystals and improve the purity of the product.

Furthermore, although not shown, an ion exchanger-packed column is provided between the solid-liquid separation device 16 and the drying device 13 in order to sufficiently remove unreacted raw material amino acids from the reaction solution. You may.

Next, a method of operating the apparatus will be described based on FIG. 5, which is a schematic diagram of an embodiment of the apparatus for producing an amino acid decarboxylation product of the present invention.

In FIG. 5, first, immobilized particles of amino acid decarboxylase are suspended in water to a predetermined concentration in a reaction tank 5, and maintained at a constant temperature under stirring. Next, starting material amino acids are added from step 3 until a predetermined pH is reached.

After waiting for the reaction to proceed and the pH to rise above the set pH, raw materials are sequentially added until a predetermined product concentration is reached. After reaching a predetermined product concentration, a slurry of raw material amino acids with a concentration corresponding to the product concentration is passed through a pH detection device! f8. Supply pump 4 linked to pH automatic adjustment device 9
At the same time, the same volume of the reaction liquid is extracted from the reaction liquid transfer pipe 10, thereby operating continuously.

Examples of the method for producing an amino acid decarboxylation product of the present invention will be described below.

Example 1 An aqueous solution 5-containing 1 x 105 units of L-glutamic acid decarboxylase originating from Escherichia coli, and aminated silica gel (φ1n) 5- were brought into contact at 40°C for 1 hour with the addition of glutaraldehyde 3-. 5.3×10′ units of L-glutamic acid decarboxylase were immobilized on silica gel particles using glutaraldehyde as a crosslinking agent. This immobilized enzyme 5
- and water 35- were placed in a 50 m (φ30 x 711 m) cylindrical reaction tank, and the gas in the gas phase of the reaction tank was circulated into the liquid at 200 mf/l lin through a single-hole nozzle installed at the bottom of the tank to remove the immobilized enzyme. The particles were fluidized. Inside the reaction tank is 4
The temperature was kept constant at 0°C, and a pH electrode was installed on the side of the reaction tank.
Set the pH to 4 or 5, which is the optimum pH for this enzyme, and
The pH can be adjusted automatically using the H automatic adjustment device.

On the other hand, a 20% slurry of L-glutamic acid crystals was prepared and supplied into the reaction tank under on-off control using a supply pump linked to the automatic pH adjustment device. After 20 hours, γ-aminobutyric acid in the reaction solution reached an equilibrium concentration of 13.
It reached 9%. The reaction molar yield was 99%.

This reaction solution was collected, and 50- was concentrated under reduced pressure to 10 m.

The L-glutamic acid crystals produced are separated by filtration and concentrated liquid 10
The 0 liquid obtained with mZ was dried under reduced pressure to obtain a pure white dry powder of 6.7
g (98% molar yield) was obtained. Purity was 99.5%. This powder contains 0.5% L-glutamic acid.

Example 2 L-glutamic acid decarboxylase derived from Kapocha 2×10S
An aqueous solution 10- containing the unit was mixed with a mixture of the following three components to obtain 30 g of a sol.

A: IN HC/! 24m Trishydroxymethylaminomethane 1.9g Distilled water
3.2-B Niacrylamide 3g Methylenebisacrylamide 0.08g Potassium ferricyanide 0.7g Distilled water 7WII C:l, 4% ammonium persulfate 2-The above sol was added to 1.
The gel plate was poured between glass walls having a gap of 5 mm, and allowed to stand at 15° C. for 40 minutes under 100 lux lighting under a nitrogen atmosphere to prepare a gel plate with a thickness of 1.5 mm.

The above-mentioned gel plate was cut into small pieces to prepare particles on which L-glutamic acid decarboxylase was immobilized.

This particle and water 120-200 d (φ40 x 160 t
m) into a cylindrical reaction tank, and the gas in the gas phase of the reaction tank was introduced into the liquid through a nozzle installed at the bottom of the tank at a rate of 300ml/lll1n.
The immobilized enzyme particles were fluidized by circulating aeration. The temperature inside the reaction tank was kept constant at 40°C, and a p
Install the H electrode and set the pH to 4, which is the optimum pH for this enzyme.
, 4, so that the pH could be automatically adjusted using an automatic pH controller.

On the other hand, a 25% slurry of L-glutamic acid crystals was prepared and supplied into the reaction tank in an on-off 1rlJi manner using a supply pump linked to the above-mentioned automatic pH controller. After 20 hours, γ-aminobutyric acid in the reaction solution reached an equilibrium concentration of 17.2%. The reaction molar yield was 98%.

This reaction solution was collected and concentrated under reduced pressure from 200- to 100-. The L-glutamic acid crystals produced were filtered off to obtain a concentrated solution 100-. Dry this solution under reduced pressure to obtain pure white dry powder 2.
7.3 g (molar yield 98%) was obtained. Purity is 99.3%
Met. This powder contains 0.2% L-glutamic acid.

Example 3 L-glutamate decarboxylase originating from the anaerobic bacterium Clostridium weltsii 1. 5 mZ of an aqueous solution containing I 'The unit was fixed.

This immobilized enzyme 5sf and water 35-50d (φ30X71
The gas from the gas phase of the reaction tank is poured into the liquid through a single-hole nozzle installed at the bottom of the tank at a rate of 200 m1/win.
Circulating aeration was performed to fluidize the immobilized enzyme particles. The temperature inside the reaction tank was kept constant at 40°C. In addition, the pH on the side of the reaction tank
Install the electrode and set the pH to 4, which is the optimum pH for this enzyme.
7, so that the pH could be automatically adjusted using an automatic pH adjustment device.

On the other hand, a 20% slurry of L-glutamic acid crystals was prepared and supplied into the reaction tank under on-off control using the supply pump linked to automatic pH adjustment and coloring. After 20 hours, the equilibrium concentration of γ-aminobutyric acid in the reaction tank was 13.
It reached 9%. The reaction molar yield was 99%.

50ml of this reaction solution was concentrated under reduced pressure to 10rsl. The L-glutamic acid crystals produced were filtered off to obtain 10 ml of a concentrated solution. Honzuke was dried under reduced pressure to obtain 6.8 g of pure white dry powder (molar yield 97%). Purity was 99.5%.

This powder contains 0.5% L-glutamic acid.

Example 4 Aqueous solution 5 containing lXl0' units of L-aspartate decarboxylase originating from the anaerobic bacterium Clostridium weltsii
- and 5 rsl of aminated silica gel (φ1ml) were brought into contact with each other at 40°C for 1 hour with the addition of 3-glutaraldehyde, and 295 units of L-glutamic acid decarboxylase were immobilized on the aminated silica gel particles.

This immobilized enzyme 5- and 35 mZ of water were added to 50 m1 (φ30×7
The gas from the gas phase of the reaction tank was poured into the liquid at a rate of 200 m1/mi through a single-hole nozzle installed at the bottom of the tank.
The particles of immobilized enzyme were fluidized by circulating aeration at n.

The temperature inside the reaction tank was kept constant at 40°C. Also, on the side of the reaction tank,
Install the H electrode and set the pH to 4, which is the optimum pH for this enzyme.
, 7, so that the pH could be automatically adjusted using an automatic pH adjustment device.

On the other hand, a 20% slurry of L-aspartic acid crystals was prepared and supplied into the reaction tank under on-off control using a supply pump linked to the automatic pH adjustment device. 20
After a period of time, the equilibrium concentration of β-alanine in the reaction tank was 13.
It reached 3%. The molar reaction yield was 99%.

50ml of this reaction solution was concentrated under reduced pressure to 10mF. The L-aspartic acid crystals produced were filtered off to obtain a concentrated solution 10mZ. Honzuke was dried under reduced pressure, and 6.5g of pure white dry powder (
A molar yield of 96%) was obtained. Purity was 79.4%.

This powder contains 4% L-aspartic acid.

Comparative Example A 40 m enzyme solution was obtained by mixing 5.3 x 10' units of the same Rondo L-glutamic acid decarboxylase used in Example 1 with 40 d of 0.5 M sodium citrate buffer.

This was placed in the cylindrical reaction tank used in Example 1, and the same -ta
L-glutamic acid slurry was fed at the same rate and at the same temperature. Stirring was also performed under the same conditions as in Example 1. pH is 6
The pH was automatically adjusted to 4.5 using NNaOH. The liquid eluted from the reaction tank was collected every hour, subjected to molecular filtration, the low molecular weight fraction was used as a reaction liquid for analysis, and the high molecular weight fraction was returned to the reaction tank along with the enzyme solution.

As a result of measuring the γ-aminobutyric acid concentration in the reaction solution after 20 hours, the molar reaction yield was 5.4%.

50 ml of this reaction solution was concentrated under reduced pressure to obtain 11.3 g of pure white dry powder. This powder contains 9.4 g of glutamic acid and 1.5 g of sodium ions. Purity was 3.4%.

As is clear from the comparison between Example 1 and Comparative Example, according to the present invention, the reaction can be carried out without using a neutralizing agent or a buffer, and the target product can be obtained with high yield and high purity.

Example 5 An aqueous solution 5- containing 500 units of diaminopimelic acid decarboxylase originating from Escherichia coli was immobilized onto aminated silica gel particles in the same manner as in Example 1 in an amount of 420 units. Using the reaction tank used in Example 1, this particle was subjected to the same operation, and a 10% slurry of diaminopimelic acid was used as the raw material liquid to pH 6,0,3.
The reaction was carried out at 8°C. After 20 hours, the concentration of lysine in the product reached equilibrium.

The reaction yield was 95%.

The reaction solution was collected and 50 rnl was concentrated under reduced pressure to 10-ml.

The resulting crystals of diaminopimelic acid were filtered off to obtain 10 ml of a concentrated solution. Honzuke is dried under reduced pressure to produce pure white dry powder 4
．． 2 g was obtained (84% molar yield). Purity was 98%. This powder contains 2% diaminopimelic acid.

〔Effect of the invention〕

Useful amino acids such as T-aminobutyric acid with high purity and
It can be synthesized without using neutralizing agents or pH buffering agents.

[Brief explanation of the drawing]

FIG. 1 is a diagram showing the time course of T-aminobutyric acid concentration and pH when reacting unimmobilized L-glutamic acid decarboxylase at various L-glutamic acid concentrations. FIG. 2 is a graph showing the time course of γ-aminobutyric acid concentration and pH when reacting immobilized L-glutamic acid decarboxylase at various L-glutamic acid concentrations. FIG. 3 is a graph showing the time course of T-aminobutyric acid concentration and pH when the substrate L-glutamic acid was added stepwise using unimmobilized L-glutamic acid decarboxylase. Figure 4 shows the concentration and p of γ-aminoacetic acid when the substrate L-glutamic acid was continuously added at a constant rate per unit time using immobilized L-glutamic acid decarboxylase.
This is an observation of the time course of H. 5 to 7 are diagrams showing a schematic diagram of an apparatus for producing an amino acid decarboxylation product of the present invention and a process flow of the present invention thereby. DESCRIPTION OF SYMBOLS 1... Raw material liquid, 2... Raw material liquid storage tank, 3... Raw material liquid transfer piping, 4... Raw material liquid transfer pump, 5... Reaction tank, 6... Reaction liquid, 7...・Piping for discharging generated carbon dioxide gas,
8... pH detection device, 9... pH automatic adjustment device, 1
0... Reaction liquid transfer piping, 11... Reaction liquid: Iil condensation lid device 2... Concentrated reaction liquid transfer piping, 13... Drying device, IA... Dry product transfer piping, 15. ... Dry product, 16... Solid-liquid separation device, 17... Unreacted raw material crystal extraction pipe, 18... Unreacted raw material crystal, 19
...Reaction product concentrate transfer piping, 20...Cooling device, 21...Cooled concentrate transfer pipe, 22...Reaction product concentrate coolant transfer pipe

Claims (1)

[Scope of Claims] 1. In producing a decarboxylated substance of the amino acid by causing immobilized amino acid decarboxylase to act on the raw material amino acid in a reaction solution, the raw material amino acid is treated with the reaction pH of the reaction solution set to the fixed value. 1. A method for producing an amino acid decarboxylation product, which comprises supplying the reaction solution in just the right amount so as to maintain the pH within the preferred action pH range of amino acid decarboxylase. 2. The method for producing an amino acid decarboxylation product according to claim 1, wherein the raw amino acid is a dibasic amino acid and the amino acid decarboxylation product is a monobasic amino acid. 3. The amino acid according to claim 1 or 2, wherein the immobilized amino acid decarboxylase is an immobilized dibasic amino acid decarboxylase whose preferred operating pH range is pH 6.5 or lower. A method for producing a decarboxylation product. 4. Claims 1 to 3, characterized in that the reaction pH is maintained only by adjusting the supply amount of raw material amino acids without using a pH buffer or a neutralizing alkali. A method for producing an amino acid decarboxylation product. 5. The raw amino acid is L-glutamic acid, the immobilized amino acid decarboxylase is immobilized L-glutamic acid decarboxylase, and the amino acid decarboxylation product is γ
-aminobutyric acid, the method for producing an amino acid decarboxylation product according to any one of claims 2 to 4. 6. Claim No. 6, characterized in that the raw amino acid is L-aspartic acid, the immobilized amino acid decarboxylase is immobilized L-aspartate decarboxylase, and the amino acid decarboxylation product is β-alanine. A method for producing an amino acid decarboxylation product according to any one of items 2 to 4. 7. Install a pH electrode in the reaction system to detect when the pH in the reaction solution is outside the preferred action pH range of the immobilized amino acid decarboxylase, and adjust the required amount of the raw material amino acid to the pH based on the detection result. Claims 1 to 6 are characterized in that the reaction solution is supplied from a supply device linked to an automatic adjustment device, and the reaction solution is drawn out of the system by the volume increased by the supply of the raw material amino acid. A method for producing an amino acid decarboxylation product according to any of the items. 8. Amino acid decarboxylation production according to any one of claims 1 to 7, characterized in that the total concentration of raw material amino acids and reaction products in the reaction solution is maintained at a high concentration of 1% or more. A method of manufacturing a substance. 9. A mixing mechanism for the reaction solution in the reaction tank, a pH detection device that detects the pH of the reaction solution in the reaction tank, a pH adjustment device that can set the pH in conjunction with the pH detection device, and a pH adjustment device. A raw material amino acid supply mechanism that supplies a required amount of raw material amino acids to the reaction tank in conjunction with the reaction tank, a particle trapping mechanism that prevents immobilized particles from flowing out from the reaction tank, and a mechanism that extracts only the reaction solution out of the tank. An apparatus for producing amino acid decarboxylation products characterized by the following. 10. Amino acid decarboxylation according to claim 9, characterized in that a reaction liquid concentration device and a drying device for drying the concentrated reaction liquid concentrated in the reaction liquid concentration device are successively connected downstream of the reaction tank. Product manufacturing equipment. 11. Production of an amino acid decarboxylated product according to claim 10, characterized in that a solid-liquid separation device is provided between the concentration device and the drying device to remove crystals of the raw material amino acid remaining in the reaction solution. Device. 12. The apparatus for producing an amino acid decarboxylated product according to claim 11, wherein the solid-liquid separator has a mechanism for cooling the raw material amino acid to a temperature suitable for crystallization. 13. The amino acid decarboxylation product production apparatus according to claim 11 or 12, characterized by having a mechanism for returning the discharged raw material amino acid crystals to a reaction tank or a raw material liquid storage tank. 14. The amino acid decarboxylation production apparatus according to claim 12, further comprising an ion exchanger packed column for selectively adsorbing raw material amino acids between the solid-liquid separation tank and the drying device.