CN114657217A - Efficient preparation method of D-pantoic acid - Google Patents
Efficient preparation method of D-pantoic acid Download PDFInfo
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- CN114657217A CN114657217A CN202111174170.8A CN202111174170A CN114657217A CN 114657217 A CN114657217 A CN 114657217A CN 202111174170 A CN202111174170 A CN 202111174170A CN 114657217 A CN114657217 A CN 114657217A
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Abstract
The invention relates to a high-efficiency preparation method of D-pantoic acid, which specifically comprises the following steps: (1) adding water into valine, methanol and a complex enzyme for mixing, wherein the complex enzyme comprises L-amino acid deaminase, methanol dehydrogenase, aldolase, formate dehydrogenase and ketopantoate reductase; (2) adding ammonium formate, and carrying out enzyme catalytic reaction at the temperature of 25-55 ℃ and under the condition that the pH value is 4-7 to obtain D-pantoic acid; wherein the amino acid sequence of valine: the molar ratio of the methanol is (0.9-1.1) to (0.9-1.1). The method takes valine and methanol as substrates to generate D-pantoic acid through fermentation and conversion, and has the advantages of low price and easy obtainment of raw materials and low reaction cost.
Description
Technical Field
The invention relates to the field of biosynthesis, and particularly relates to a high-efficiency preparation method of D-pantoic acid.
Background
Pantothenic acid also called vitamin B5For feeding to humans and domestic animalsEssential nutrient elements of dairy animals and are used for biosynthesizing coenzyme A (CoA) and Acyl Carrier Protein (ACP) in body cells, thereby participating in more than one hundred kinds of cell metabolic reactions.
D-pantolactone is an important precursor for the synthesis of D-pantothenic acid. CN110423717A discloses a preparation method of D-pantolactone, which comprises the step of carrying out enzymatic selective hydrolysis separation or enzymatic catalytic synthesis on DL-pantolactone to prepare the D-pantolactone. But has the defects that the synthesis of DL-pantoic acid lactone needs to use a large amount of isobutyraldehyde and formaldehyde, the formaldehyde has irritation harm to human bodies, the formaldehyde is extracted and separated by adopting an organic reagent, the reaction substrate is expensive, the racemic intermediate product needs to be resolved (such as the resolution of DL-pantoic acid lactone to obtain D-pantoic acid lactone for polymerization with beta-alanine), and the economic benefit and the environmental benefit are not satisfactory.
CN108456701A discloses a preparation method of D-pantolactone. The method takes valine as a substrate and prepares D-pantolactone through multi-enzyme combined catalysis. But has the defects of complicated reaction steps, long reaction time, high cost caused by the consumption of coenzyme NADPH in the process of converting ketopantoate into pantoate, and the like, and limits the industrialized application prospect of the ketopantoate.
Disclosure of Invention
The invention aims to provide an efficient preparation method of D-pantoic acid, which comprises the following steps:
(1) adding water to valine, methanol and a complex enzyme for mixing, wherein the complex enzyme comprises L-amino acid deaminase, methanol dehydrogenase, aldolase, formate dehydrogenase and ketopantoate reductase;
(2) adding ammonium formate, and carrying out enzyme catalytic reaction at the temperature of 25-55 ℃ and under the condition that the pH value is 4-7 to obtain D-pantoic acid; wherein the amino acid sequence of valine: the molar ratio of methanol is (0.9-1.1) to (0.9-1.1), preferably (0.95-1.05) to (0.95-1.05).
According to the preferred technical scheme, the ammonium formate is added in a fed-batch mode.
In the preferred technical scheme of the invention, the concentration of the ammonium formate is 1.5g/L-2.5g/L, preferably 1.8g/L-2.2 g/L.
According to the preferable technical scheme, the L-amino acid deaminase in the compound enzyme is 4-15U/L, and preferably 6-10U/L.
According to the preferable technical scheme, the methanol dehydrogenase in the complex enzyme is 4-15U/L, and preferably 6-10U/L.
According to the preferable technical scheme, the aldolase in the complex enzyme is 10-20U/L, and preferably 15-17U/L.
According to the preferable technical scheme, the formate dehydrogenase in the complex enzyme is 4-15U/L, and preferably 6-10U/L.
According to the preferable technical scheme, the ketopantoate reductase in the compound enzyme is 4-15U/L, and preferably 6-13U/L.
In the preferable technical scheme of the invention, metal salt or phosphate solution can be added into the enzyme catalysis system.
In a preferred embodiment of the present invention, the metal salt or phosphate is selected from any one of zinc salt, calcium salt, copper salt, magnesium salt, sodium salt, and potassium salt, or a combination thereof, and is preferably selected from any one of magnesium chloride, zinc chloride, calcium chloride, copper chloride, sodium chloride, potassium chloride, sodium sulfate, sodium bisulfate, potassium sulfate, magnesium sulfate, zinc sulfate, calcium sulfate, copper sulfate, magnesium phosphate, zinc phosphate, calcium phosphate, copper phosphate, ammonium dihydrogen phosphate, diammonium hydrogen phosphate, disodium hydrogen phosphate, sodium dihydrogen phosphate, calcium hydrogen phosphate, calcium pyrophosphate, potassium dihydrogen phosphate, dipotassium hydrogen phosphate, sodium acid pyrophosphate, sodium phosphate, and sodium pyrophosphate, or a combination thereof.
According to the preferable technical scheme, the concentration of the metal salt or phosphate solution is 0-50mM, preferably 1-40 mM, and more preferably 5-30 mM.
Preferred technical scheme of the invention, Zn in metal salt solution2+The concentration is 0 to 15mM, preferably 5 to 10 mM.
Preferred technical solution of the present invention, Cu in metal salt solution2+The concentration is 0 to 15mM, preferably 5 to 10 mM.
Preferred technical solution of the present invention, Ca in the metal salt solution2+The concentration is 0 to 9mM, preferably 2 to 7 mM.
In a preferred embodiment of the invention, Mg is present in a metal salt solution2+The concentration is 0-9mM, preferably 2-7 mM.
In the preferred embodiment of the present invention, Na is contained in the metal salt solution+The concentration is 0-9mM, preferably 2-7 mM.
Preferred embodiment of the invention, PO in phosphate solution4 3-The concentration is 0 to 15mM, preferably 2 to 10 mM.
Preferred embodiment of the invention, HPO in phosphate solution4 2-The concentration is 0 to 15mM, preferably 2 to 10 mM.
Preferred embodiment of the invention, H in phosphate solution2PO4 -The concentration is 0 to 15mM, preferably 2 to 10 mM.
According to the preferable technical scheme, the temperature of the enzyme catalysis reaction is 30-40 ℃, and is preferably 35-37 ℃.
According to the preferable technical scheme, the pH value of an enzyme catalysis reaction system is 5-7.
In a preferred embodiment of the present invention, the pH adjusting agent for adjusting the pH of the enzymatic reaction system is selected from any one of ammonia, sodium hydroxide, sodium bicarbonate, triethylamine, potassium hydroxide, sodium phosphate, sodium citrate, sodium malate, phosphate buffer, Tris buffer, and sulfuric acid.
Another object of the present invention is to provide a use of D-pantoic acid for the preparation of panto-compounds selected from any one of D-pantolactone, calcium-D-pantoate, D-panthenol, pantethine.
The invention also aims to provide a preparation method of D-pantoic acid lactone, which takes the D-pantoic acid prepared by the method to obtain the D-pantoic acid lactone through lactonization.
According to the preferable technical scheme, the lactonization reaction comprises the steps of taking a reaction solution of D-pantoic acid, passing through a ceramic membrane, collecting a clear solution, passing through a nanofiltration membrane, collecting a clear solution, adjusting the pH value of the clear solution to be below 3.0 by using sulfuric acid, and stirring the clear solution at the temperature of between 30 and 80 ℃ for reaction; adding an alkali solution, and adjusting the pH value of the solution to 4-7 to obtain the D-pantoic acid lactone.
According to the preferable technical scheme, the lactonization reaction comprises the steps of taking a reaction solution of D-pantoic acid, passing through a ceramic membrane, collecting a clear solution, passing through a nanofiltration membrane, collecting a clear solution, adjusting the pH value of the clear solution to be below 2.0 by using sulfuric acid, and stirring the clear solution at the temperature of 40-60 ℃ for reaction; adding 0.1mol/L NaOH solution, adjusting the pH value of the solution to 5-7, and obtaining the D-pantoic acid lactone.
Unless otherwise indicated, when the present invention relates to percentages between liquids, said percentages are volume/volume percentages; the invention relates to the percentage between liquid and solid, said percentage being volume/weight percentage; the invention relates to the percentages between solid and liquid, said percentages being weight/volume percentages; the balance being weight/weight percent.
Unless otherwise stated, the present invention measures conversion and yield as follows.
1. Enzyme activity
The enzyme activity (unit is U) is a measurement unit of the enzyme activity. Each enzyme activity unit of the present invention represents the amount of enzyme required for the conversion of 1ml of substrate solution to 1umol of D-pantoic acid in 1 minute.
2. Conversion rate
Instruments and working conditions: a chromatographic column: inertsil NH2 5um 4.6*250mm；
Mobile phase: acetonitrile: 0.04moL/L potassium dihydrogen phosphate in water (pH 3.0 adjusted with phosphoric acid) 75: 25; column temperature: 30 ℃; wavelength: 205 nm; flow rate: 1.0 mL/min; sample introduction amount: 5 uL.
Diluting the reaction solution by 100 times when the conversion time T is 0 and T is M (M is any value more than 0), filtering, injecting sample with 10ul, and recording the concentration S of valine0And SMThe D-pantoic acid concentration is Nm.
Conversion (M time) 0.79 Nm/(S)0-SM)。
Compared with the prior art, the invention has the following beneficial effects:
1. the invention uses methanol as a substrate, effectively avoids leakage caused by directly adding formaldehyde, is beneficial to protecting the environment and the safety of production workers, saves the cost and is suitable for industrial production.
2. The invention converts the formic acid into volatile carbon dioxide, which is beneficial to improving the reaction efficiency, avoids the complicated steps caused by separating and removing the formic acid, shortens the production period, and reduces the generation of three wastes and the recovery and treatment cost thereof.
Drawings
FIG. 1 conversion of examples 1-6 and comparative example 1;
FIG. 2D-pantolactone yields of examples 1-6 and comparative example 1.
Detailed Description
The present invention will be further described with reference to the following examples.
Unless otherwise specified, the experimental methods used in the examples are all conventional methods, and the materials, reagents and the like used therein are commercially available.
Example 1
1) Adding valine, methanol and a complex enzyme into a reaction container, adding water until the total volume is 5L, and stirring for dissolving to ensure that: 249.5g valine, 68.25g methanol, 10U/L-amino acid deaminase, 10U/L methanol dehydrogenase, 15U/L aldolase, 13U/L ketopantoate reductase, 12U/L formate dehydrogenase. Ammonium formate is fed in a flow manner, and the concentration of the ammonium formate in the reaction liquid is maintained to be 2 g/L. Adjusting the temperature of the solution to 37 ℃, adjusting the pH of the solution to 5-7 by using ammonia water and dilute sulfuric acid, continuously reacting for 20h under the stirring condition to obtain a D-pantoic acid solution, and detecting the conversion rate as shown in figure 1.
2) Taking the D-pantoic acid reaction solution, passing through a ceramic membrane, collecting clear solution, passing through a nanofiltration membrane, collecting clear solution, adjusting the pH of the clear solution to be below 2.0 by using sulfuric acid, and stirring and reacting at 50 ℃ for 0.5 hour; adding 0.1mol/L NaOH, adjusting the pH value of the solution to 6.0, concentrating, crystallizing, and obtaining D-pantolactone, wherein the yield is shown in figure 2.
Example 2
1) Adding valine, methanol and a complex enzyme into a reaction container, adding water until the total volume is 5L, and stirring for dissolving to ensure that: 249.5g of valine, 68.25g of methanol, 10U/L of L-amino acid deaminase, 10U/L of methanol dehydrogenase, 18U/L of aldolase, 14U/L of ketopantoate reductase and 12U/L of formate dehydrogenase. Ammonium formate is fed in a flow manner, and the concentration of the ammonium formate in the reaction liquid is maintained to be 2 g/L. Adjusting the temperature of the solution to 37 ℃, adjusting the pH of the solution to 5-7 by using ammonia water and dilute sulfuric acid, continuously reacting for 20h under the stirring condition to obtain a D-pantoic acid solution, and detecting the conversion rate as shown in figure 1.
2) Taking the D-pantoic acid reaction solution, passing through a ceramic membrane, collecting clear solution, passing through a nanofiltration membrane, collecting clear solution, adjusting the pH value of the clear solution to be below 2.0 by using sulfuric acid, and stirring and reacting for 0.5 hour at 50 ℃; adding 0.1mol/L NaOH, adjusting the pH value of the solution to 6.0, concentrating, crystallizing, and obtaining D-pantolactone, wherein the yield is shown in figure 2.
Example 3
1) Adding valine, methanol and a complex enzyme into a reaction container, adding water until the total volume is 5L, and stirring for dissolving to ensure that: 300g of valine, 85g of methanol, 10U/L of L-amino acid deaminase, 10U/L of methanol dehydrogenase, 18U/L of aldolase, 14U/L of ketopantoate reductase and 12U/L of formate dehydrogenase. Ammonium formate is fed in a flow manner, and the concentration of the ammonium formate in the reaction liquid is maintained to be 2 g/L. Adjusting the temperature of the solution to 37 ℃, adjusting the pH of the solution to 5-7 by using ammonia water and dilute sulfuric acid, continuously reacting for 20h under the stirring condition to obtain a D-pantoic acid solution, and detecting the conversion rate as shown in figure 1.
2) Taking the D-pantoic acid reaction solution, passing through a ceramic membrane, collecting clear solution, passing through a nanofiltration membrane, collecting clear solution, adjusting the pH value of the clear solution to be below 2.0 by using sulfuric acid, and stirring and reacting for 0.5 hour at 50 ℃; adding 0.1mol/L NaOH, adjusting the pH value of the solution to 6.0, concentrating, crystallizing, and obtaining D-pantolactone, wherein the yield is shown in figure 2.
Example 4
1) Adding valine, methanol, zinc chloride and complex enzyme into a reaction container, adding water until the total volume is 5L, stirring and dissolving to ensure that: 249.5g of valine, 68.25g of methanol, 10g of zinc chloride, 10U/L of L-amino acid deaminase, 10U/L of methanol dehydrogenase, 18U/L of aldolase, 14U/L of ketopantoate reductase and 12U/L of formate dehydrogenase. Ammonium formate is fed in a flow manner, and the concentration of the ammonium formate in the reaction liquid is maintained to be 2 g/L. Adjusting the temperature of the solution to 37 ℃, adjusting the pH of the solution to 5-7 by using ammonia water and dilute sulfuric acid, continuously reacting for 20h under the stirring condition to obtain a D-pantoic acid solution, and detecting the conversion rate as shown in figure 1.
2) Taking the D-pantoic acid reaction solution, passing through a ceramic membrane, collecting clear solution, passing through a nanofiltration membrane, collecting clear solution, adjusting the pH value of the clear solution to be below 2.0 by using sulfuric acid, and stirring and reacting for 0.5 hour at 50 ℃; adding 0.1mol/L NaOH, adjusting the pH value of the solution to 6.0, concentrating, crystallizing, and obtaining D-pantolactone, wherein the yield is shown in figure 2.
Example 5
1) Adding valine, methanol, copper sulfate and complex enzyme into a reaction vessel, adding water until the total volume is 5L, stirring and dissolving to ensure that: 249.5g of valine, 68.25g of methanol, 10g of copper sulfate, 10U/L of L-amino acid deaminase, 10U/L of methanol dehydrogenase, 18U/L of aldolase, 14U/L of ketopantoate reductase and 12U/L of formate dehydrogenase. Ammonium formate is fed in a flow manner, and the concentration of the ammonium formate in the reaction liquid is maintained to be 2 g/L. Adjusting the temperature of the solution to 37 ℃, adjusting the pH of the solution to 5-7 by using ammonia water and dilute sulfuric acid, continuously reacting for 20h under the stirring condition to obtain a D-pantoic acid solution, and detecting the conversion rate as shown in figure 1.
2) Taking the D-pantoic acid reaction solution, passing through a ceramic membrane, collecting clear solution, passing through a nanofiltration membrane, collecting clear solution, adjusting the pH value of the clear solution to be below 2.0 by using sulfuric acid, and stirring and reacting for 0.5 hour at 50 ℃; adding 0.1mol/L NaOH, adjusting the pH value of the solution to 6.0, concentrating, crystallizing, and obtaining D-pantolactone, wherein the yield is shown in figure 2.
Example 6
1) Adding valine, methanol, disodium hydrogen phosphate and complex enzyme into a reaction container, adding water until the total volume is 5L, stirring and dissolving to ensure that: 249.5g of valine, 68.25g of methanol, 7g of disodium hydrogen phosphate, 10U/L of L-amino acid deaminase, 10U/L of methanol dehydrogenase, 18U/L of aldolase, 14U/L of ketopantoate reductase and 12U/L of formate dehydrogenase. Ammonium formate is fed in a flow manner, and the concentration of the ammonium formate in the reaction liquid is maintained to be 2 g/L. Adjusting the temperature of the solution to 37 ℃, adjusting the pH of the solution to 5-7 by using ammonia water and dilute sulfuric acid, continuously reacting for 20 hours under the stirring condition to obtain a D-pantoic acid solution, and detecting the conversion rate as shown in figure 1.
2) Taking the D-pantoic acid reaction solution, passing through a ceramic membrane, collecting clear solution, passing through a nanofiltration membrane, collecting clear solution, adjusting the pH value of the clear solution to be below 2.0 by using sulfuric acid, and stirring and reacting for 0.5 hour at 50 ℃; adding 0.1mol/L NaOH, adjusting the pH value of the solution to 6.0, concentrating, crystallizing, and obtaining D-pantolactone, wherein the yield is shown in figure 2.
Comparative example 1
1) Adding valine, methanol and complex enzyme into a reaction vessel, adding water until the total volume is 5L, stirring and dissolving to ensure that: 249.5g valine, 68.25g methanol, 7g disodium hydrogen phosphate, 10U/L catalase, 10U/L ketoisovalerate reductase, 18U/L hydroxymethyltransferase, 12U/L formate dehydrogenase. Ammonium formate is fed in a flow manner, and the concentration of the ammonium formate in the reaction liquid is maintained to be 2 g/L. Adjusting the temperature of the solution to 37 ℃, adjusting the pH value of the solution to 5-7, continuously reacting for 20h under the stirring condition to obtain a D-pantoic acid solution, and detecting the conversion rate shown in figure 1.
2) Taking the D-pantoic acid reaction solution, passing through a ceramic membrane, collecting clear solution, passing through a nanofiltration membrane, collecting clear solution, adjusting the pH value of the clear solution to be below 2.0 by using sulfuric acid, and stirring and reacting for 0.5 hour at 50 ℃; 0.1mol/L NaOH is added to adjust the pH of the solution to 6.0, and D-pantolactone is prepared, and the yield is shown in figure 2.
Claims (10)
1. A high-efficiency preparation method of D-pantoic acid comprises the following steps:
(1) adding water into valine, methanol and a complex enzyme for mixing, wherein the complex enzyme comprises L-amino acid deaminase, methanol dehydrogenase, aldolase, formate dehydrogenase and ketopantoate reductase;
(2) adding ammonium formate, and carrying out enzyme catalytic reaction at the temperature of 25-55 ℃ and under the condition that the pH value is 4-7 to obtain D-pantoic acid; wherein the amino acid sequence of valine: the molar ratio of methanol is (0.9-1.1) to (0.9-1.1), preferably (0.95-1.05) to (0.95-1.05).
2. The process according to claim 1, wherein the ammonium formate is added in fed-batch mode, preferably at a concentration of 1.5-2.5 g/L, more preferably 1.8-2.2 g/L.
3. The preparation method of any one of claims 1-2, wherein the amount of L-amino acid deaminase in the complex enzyme is 4-15U/L, preferably 6-10U/L.
4. The preparation method of any one of claims 1 to 3, wherein the methanol dehydrogenase in the complex enzyme is 4 to 15U/L, preferably 6 to 10U/L.
5. The process according to any one of claims 1 to 4, wherein the aldolase in the complex enzyme is 10 to 20U/L, preferably 15 to 17U/L.
6. The method according to any one of claims 1 to 5, wherein the formate dehydrogenase is present in the complex enzyme at 4 to 15U/L, preferably 6 to 10U/L.
7. The process according to any one of claims 1 to 6, wherein the ketopantoate reductase in the complex enzyme is 4 to 15U/L, preferably 6 to 13U/L.
8. The preparation method according to any one of claims 1 to 7, wherein a metal salt or a phosphate solution is further added to the enzyme catalysis system, preferably, the metal salt or phosphate is selected from any one or a combination of zinc salt, calcium salt, copper salt, magnesium salt, sodium salt, potassium salt, and more preferably, any one or a combination of magnesium chloride, zinc chloride, calcium chloride, copper chloride, sodium chloride, potassium chloride, sodium sulfate, sodium bisulfate, potassium sulfate, magnesium sulfate, zinc sulfate, calcium sulfate, copper sulfate, magnesium phosphate, zinc phosphate, calcium phosphate, copper phosphate, ammonium dihydrogen phosphate, diammonium hydrogen phosphate, disodium hydrogen phosphate, sodium dihydrogen phosphate, calcium pyrophosphate, potassium dihydrogen phosphate, dipotassium hydrogen phosphate, sodium acid pyrophosphate, sodium phosphate, and sodium pyrophosphate.
9. Use of D-pantoic acid in the preparation of a panto-compound selected from any one of D-pantolactone, calcium D-pantothenate, D-panthenol, pantethine.
10. A process for producing D-pantoic acid lactone, which comprises subjecting D-pantoic acid produced by the process according to any one of claims 1 to 8 to lactonization to produce D-pantoic acid lactone.
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Application publication date: 20220624 |