CN106350547A - Preparation method of L-arginine-alpha-ketoglutaric acid - Google Patents
Preparation method of L-arginine-alpha-ketoglutaric acid Download PDFInfo
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Abstract
The invention provides a preparation method of L-arginine-alpha-ketoglutaric acid. A method for separating a mixed solution of an alpha-ketoglutaric acid enzyme conversion solution and an arginine fermentation solution to extract arginine-alpha-ketoglutaric acid is utilized; according to the process, the enzyme conversion solution is firstly obtained by utilizing an enzyme catalysis method; after thalli in the conversion solution are removed, the conversion solution passes through a cation column to collect an alpha-ketoglutaric acid solution for later use; then, the arginine fermentation solution is obtained through a direct fermentation method and the thalli, almost protein and pigments in the fermentation solution are removed through membrane filtering; a membrane filtering solution passes through the cation column and arginine is adsorbed; then the solution is eluted with ammonia water and an arginine high fraction is collected; after deamination is carried out, an arginine solution is obtained; the two solutions are mixed according to the equal mol ratio of an alpha-ketoglutaric acid enzyme and the arginine; then operation units of de-colording by active carbon, decompressing and concentrating in vacuum, spraying and drying a finished product and the like are used for obtaining an arginine-alpha-ketoglutaric acid crystal with the purity of 98.0 percent and the yield reaches 82 percent or more.
Description
Technical field
The present invention relates to the technical field of fermentative Production organic acid, especially a kind of l- arginine-α-ketoglutaric acid
Preparation method.
Background technology
L- arginine-alpha-ketoglutarate (l-arginine- α-ketoglutarate, aakg), referred to as smart ketone mixture,
It is the amino acid salts being formed by l-l- arginine (l-arg) and α-ketoglutaric acid (α-kg) complexation, can be with salt from solution
Form crystallization separates out.Under different crystallization conditions, aakg can form single arginine ketoglutarate (maakg) and double essence ammonia
Sour two kinds of forms of ketoglutarate (daakg), study and apply more mainly maakg at present, and its crystal formation is colourless prism
Shape, soluble in water, be slightly soluble in ethanol, insoluble in acetone, ether etc., can will be completely dissociated in aqueous for l- arginine and α-
Ketoglutaric acid.The aakg studying herein refers both to maakg, and its structural formula is as follows:
Aakg not only has the physiological function of l- arginine and α-ketoglutaric acid concurrently, and can strengthen as functional nutrient
Agent and liver-protecting medicine are applied to clinic.α-ketoglutaric acid directly can quickly promote tricarboxylic acid cycle in human body (tca circulation), produces
More substantial cellular energy (atp) come to supply impaired hepatocyte make hepatocyte keep normal function so that liver can be able to
The operating of normal health；L- arginine directly rapidly joins urea cycle (ornithine cycle) simultaneously, make in blood ammonia poison by
Turn ammonia and deammoniation dual function to remove the hyperammonemia caused by hepatic disease, make liver recover normal function and health.Separately
Outward, aakg can be additionally used in strengthening physique, promotes the rapid growth of muscle and wound to recover, and promotes hepatocyte to nutrition and energy
Metabolism, gains in strength and energy, and its physiological mechanism is that aakg can improve the level of internal no in a short time, strengthens protein
Assimilation.At present, as functional food, sales volume increasingly increases aakg in the international market, and with guanyl ketoglutarate
(okg) together, in medical science, nutrition, Sports Field attention.
The preparation technology of aakg mainly has three kinds of modes: direct mixing method, lyophilization and crystallization process at present.
Direct mixing method is simply to be mixed equimolar l- arginine, α-ketoglutaric acid powder, its system
Preparation Method is simple, and cost is relatively low, is merchandized handling method the most general.But the aakg that this method produces is not crystal type to be produced
Product, do not have therebetween sat linkage to combine, and product quality is affected by the quality of raw material, the uniformity of mixing.
Lyophilization is to carry out equimolar and mix and dissolve l- arginine, α-ketoglutaric acid powder, then will be dry for solution freezing
Dry become lyophilized powder, this technique can obtain metastable crystal type aakg, but has that crystal formation is uncontrollable, freeze-drying process energy consumption
Big the problems such as, typically it is suitable only for aakg injection and produces.
Crystallization process be by l- arginine, α-ketoglutaric acid in equimolar ratio miscible after, concentrated by solution or add
The methods such as organic solvent, reduction temperature, make aakg separate out with crystal form, its product purity is high, quality controllable.Comparatively speaking,
Mixing method and lyophilization, can not remove the impurity that raw material is brought in preparation process, have higher requirement to material quality,
And crystallization processes are one and can effectively go deimpurity subtractive process it is thus possible to use the relatively low raw material of purity, or even
It is the fermentation liquid of low concentration.
The α-ketoglutaric acid source being related in Chinese patent cn 102531968a extract in smart ketone mixture technique is to pass through
2,2- dichloro Glutaric Acid Dimethyl ester reactions obtain, and its synthetic route is longer, employs substantial amounts of organic solvent, the murder by poisoning to human body
Larger, it is not suitable for as food and medicinal product raw material；Be related in Chinese patent cn 102020593a α in extraction process-
Ketoglutaric acid is obtained by fermentable, and its fermentation liquid byproduct compounds is complicated (especially organic in metabolic process
The accumulation of acid), the later stage is extracted and causes certain interference.
Content of the invention
The technical problem to be solved is to provide a kind of preparation method of l- arginine-α-ketoglutaric acid.
For solving above-mentioned technical problem, the technical scheme is that
A kind of preparation method of l- arginine-α-ketoglutaric acid (smart ketone mixture), step is as follows:
(1) prepare α-ketoglutaric acid solution: paddy ammonia is expressed using escherichia coli bl21 (de3) (escherichia coli)
Acid oxidase, with l- glutamic acid as substrate, obtains α-ketoglutaric acid enzymatic conversion liquid by enzyme transforming process, and enzymatic conversion liquid passes through micro-
Filter, ultrafiltration, obtain α-ketoglutaric acid solution after ion exchange remove impurity；
(2) prepare l- arginine solution: using Corynebacterium glutamicum (corynebacterium glutamicum) fermentation
L- arginine, obtains l- arginine fermentation liquid, obtains l- arginine solution after microfiltration, ultrafiltration, ion exchange, deamination；
(3) mixed crystallization: α-ketoglutaric acid solution is mixed according to equimolar ratio with l- arginine solution, is adjusted to ph
For 4.0 ± 0.5, carry out concentrating under reduced pressure, spray drying after decolouring, obtain final product.
Above-mentioned arginine production bacterium Corynebacterium glutamicum is conventional production bacterial strain, escherichia coli bl21 (de3) is that market leads to
Use strain.
Preferably, the preparation method of above-mentioned l- arginine-α-ketoglutaric acid, specifically comprises the following steps that
(1) α-ketoglutaric acid enzymatic conversion liquid and arginine fermentation liquid are inactivated through viable bacteria, adjusting ph with dilute hydrochloric acid is 4.0-
4.5, enter microfiltration film separation system and carry out microfiltration, respectively obtain the α-ketoglutaric acid micro-filtrate removing thalline and arginine microfiltration
Liquid；Operation temperature is 10-50 DEG C, and entering film pressure with membrane pressure differential is 0.05-0.1mpa, and filter process adds purification several times
Water top is washed, until α-ketoglutaric acid and arginic content are less than shutdown after 2.0g/l in solution, obtains α-ketoglutaric acid microfiltration
Liquid and arginine micro-filtrate；
(2) the α-ketoglutaric acid micro-filtrate of step (1) gained clarification and arginine micro-filtrate are pumped into ultrafilter membrane mistake respectively
Filter, filters removing protein, and its operating condition is ph 2-12, temperature 10-50 DEG C, and operating pressure difference (enters film pressure and goes out film pressure
Difference) it is 0.05-0.1mpa, obtain α-ketoglutaric acid ultrafiltrate and arginine ultrafiltrate；
(3) by 732 cation exchange resiies on step (2) gained α-ketoglutaric acid ultrafiltrate (absorption sodium ion, glutamic acid
The impurity such as cation), collect the α-ketoglutaric acid effluent that ph is less than 2.0；732 cation exchange resiies on arginine filtrate
Absorption, deionized water backwash after saturation to be adsorbed, adopt the ammonia eluting of 3-8% afterwards, collect the arginine that ph is 9-11
High flow point eluent, eluent obtains l- arginine solution after deamination；
(4) step (3) gained α-ketoglutaric acid effluent and l- arginine solution are carried out according to the ratio of mol ratio 1:1
Mixing, being adjusted to ph is 4.0 ± 0.5, obtains arginine-α-ketoglutaric acid mixed liquor；
(5) activated carbon decolorizing of 1.5-2.0%, temperature are added in step (4) gained arginine-α-ketoglutaric acid mixed liquor
60 DEG C of degree, stirring decolouring 25min, it is filtrated to get arginine-α-ketoglutaric acid mixing destaining solution；
(6) step (5) gained arginine-α-ketoglutaric acid mixing destaining solution is carried out being evaporated to substance hydrops
12-18%, obtains arginine-α-ketoglutaric acid mixed concentrated liquid；
(7) step (6) gained arginine-α-ketoglutaric acid mixed concentrated liquid is spray-dried, is obtained final product target product
(being a kind of l- arginine-α-ketoglutaric acid mixture powder).
Preferably, the preparation method of above-mentioned l- arginine-α-ketoglutaric acid, described microfiltration film separation system adopts hollow
Fiber film separation system, microfiltration membrane aperture is 0.1um.
Preferably, the preparation method of above-mentioned l- arginine-α-ketoglutaric acid, described ultrafiltration membrane filter adopts hollow fine
Dimension film separation system, molecular cut off is 6000.
Preferably, the preparation method of above-mentioned l- arginine-α-ketoglutaric acid, described microfiltration film separation system is that hollow is fine
Dimension film separation system, microfiltration membrane aperture is 0.1um.
Preferably, the preparation method of above-mentioned l- arginine-α-ketoglutaric acid, described ultrafiltration membrane filter adopts hollow fine
Dimension film separation system, molecular cut off is 6000.
Preferably, the preparation method of above-mentioned l- arginine-α-ketoglutaric acid, described arginine-α-ketoglutaric acid mixed liquor
After activated carbon decolorizing, solution light transmittance is more than 90%.
Present configuration has the advantages that:
The preparation method of above-mentioned l- arginine-α-ketoglutaric acid, has the following technical effect that
(1) obtain α-ketoglutaric acid enzymatic conversion liquid using by enzymatic conversion l- glutamic acid, adopt l- arginine to produce simultaneously
Bacterium fermentation obtain l- arginine fermentation liquid, by enzymatic conversion liquid and fermentation liquid are carried out microfiltration, ultrafiltration, ion exchange, deamination take off
Color etc. is processed, and carries out decolouring, the operation of the unit such as concentrating under reduced pressure, spray drying after the two equimolar ratio is mixed；And using micro-
Filter and the double membrane filtration tropina of ultrafiltration, remove tropina effect preferably, filtrate clear；
(2) adopt cation exchange technique, efficiently the impurity such as difficult detached glutamic acid of removal, the l- arginine-α obtaining-
Ketoglutaric acid is analyzed its purity through high performance liquid chromatography detection and is reached more than 98.0%.
Brief description
Fig. 1 is l- arginine-α-ketoglutaric acid of the present invention (smart ketone mixture) extraction process flow chart.
Specific embodiment
For further illustrating the present invention, now cooperation accompanying drawing is described in detail:
Embodiment 1
A kind of preparation method of l- arginine-α-ketoglutaric acid, specifically comprises the following steps that
A, take α-ketoglutaric acid enzymatic conversion liquid and l- arginine fermentation liquid 32.0l and 18.1l (α-ketoglutaric acid and l- respectively
Arginine content is respectively 31.2g/l and 65.8g/l) heat more than 10min in 80 DEG C, adjusting ph with hydrochloric acid is 4.0, enters in a subtle way
Membrane separation system carries out microfiltration, respectively obtains the α-ketoglutaric acid micro-filtrate removing thalline and l- arginine micro-filtrate；Described
Microfiltration film separation system adopts Middle hollow fiber membrane system, and microfiltration membrane aperture is 0.1um, and operation temperature is 30 DEG C, enters mould
Power and membrane pressure differential are 0.05mpa, and filter process adds purified water top to wash several times, until α-ketoglutaric acid and l- in solution
Arginic content is shut down after being less than 2.0g/l, obtains α-ketoglutaric acid micro-filtrate and l- arginine micro-filtrate.
B, by through a step obtain clarify α-ketoglutaric acid micro-filtrate and l- arginine micro-filtrate pump into ultrafiltration membrane filter,
Removing protein and desolventing technology are carried out to filtrate, respectively obtains α-ketoglutaric acid ultrafiltrate and l- arginine ultrafiltrate；Described super
Membrane filter adopts Middle hollow fiber membrane system, and molecular cut off is 6000, and its operating condition is ph 4.0, operation temperature
30 DEG C, entering film pressure with membrane pressure differential is 0.08mpa.
C, by b step obtain α-ketoglutaric acid ultrafiltrate on 732 cationic exchange resin adsorption sodium ion, glutamic acid sun from
The impurity such as son, collect the α-ketoglutaric acid effluent that ph is less than 2.0；732 cationic exchange resin adsorption on arginine filtrate,
Deionized water backwash after saturation to be adsorbed, the ammonia eluting adopting 6% afterwards (can be the ammonia of any concentration of 3-8%
Carry out eluting), collect the arginine high flow point eluent that ph is 9-11, eluent obtains l- arginine solution after deamination.
D, α-ketoglutaric acid effluent c being walked acquisition and arginine solution mix according to the ratio of mol ratio 1:1 respectively,
Ph is 4.0, obtains arginine-α-ketoglutaric acid mixed liquor；
E, d is walked in arginine-α-ketoglutaric acid mixed liquor add 1.8% activated carbon decolorizing, temperature 60 C, stirring
Decolouring 25min, is filtrated to get arginine-α-ketoglutaric acid mixing destaining solution, light transmittance be 97.5% (generally it is ensured that
It is filtrated to get arginine-α-ketoglutaric acid and mixes the light transmittance of destaining solution more than 97.0%)；
F, d is walked in arginine-α-ketoglutaric acid mixing destaining solution carry out being evaporated to the 17% of substance hydrops, obtain
To arginine-α-ketoglutaric acid mixed concentrated liquid；
G, f is walked in arginine-α-ketoglutaric acid mixed concentrated liquid be spray-dried, obtain l- arginine-α -one
1,3-propanedicarboxylic acid mixture powder.
H, the l- arginine-α-ketoglutaric acid crystal obtaining g step, weigh 1801.7g, and calculated yield is 82.3%, pure
Spend for 98.1%.
To sum up, the preparation method of l- arginine-α-ketoglutaric acid of the present invention, using fermentative Production l- arginine,
Enzymatic conversion liquid and fermentation liquid contain α-ketoglutaric acid and l- arginine respectively, in addition also thalline, water-solubility protein, color
Element, sodium glutamate etc., according to the feature of enzymatic conversion liquid and fermentation liquid, first passing through double films is micro-filtration membrane, Ultra filtration membrane system
System cross flow filter removes thalline, most of albumen and pigment, and membrane filtration liquid passes sequentially through cation exchange column and removes impurity, obtains
α-ketoglutaric acid and arginine high flow point solution, by both according to dense by activated carbon decolorizing, decompression after the mixing of equimolar ratio
Contracting, spray drying obtain the l- arginine-α-ketoglutaric acid crystal of purity 98.0%, and yield reaches more than 82.0%.Described system
Preparation Method efficiently solves the complexity of separation-extraction technology present in existing production technology, and yield is low, and product purity is low, a large amount of systems
The problems such as standby high cost, using add from the enzymatic conversion liquid of α-ketoglutaric acid l- arginine fermentation liquid produce l- arginine-α-
Ketoglutaric acid, has with short production cycle, by-product is few, the advantages of separation and Extraction is relatively easy.
The above is only the preferred embodiment of the present invention it is noted that ordinary skill people for the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (7)
1. a kind of preparation method of l- arginine-α-ketoglutaric acid it is characterised in that: step is as follows:
(1) prepare α-ketoglutaric acid solution: dglutamic oxidase is expressed using escherichia coli bl21 (de3), with l- glutamic acid is
Substrate, obtains α-ketoglutaric acid enzymatic conversion liquid by enzyme transforming process, and enzymatic conversion liquid is after microfiltration, ultrafiltration, ion exchange remove impurity
Obtain α-ketoglutaric acid solution；
(2) prepare l- arginine solution: using Corynebacterium glutamicum fermentation l- arginine, obtain l- arginine fermentation liquid, pass through
Microfiltration, ultrafiltration, ion exchange, obtain l- arginine solution after deamination；
(3) mixed crystallization: α-ketoglutaric acid solution is mixed according to equimolar ratio with l- arginine solution, being adjusted to ph is
4.0 ± 0.5, carry out concentrating under reduced pressure, spray drying after decolouring, obtain final product.
2. l- arginine-α-ketoglutaric acid according to claim 1 preparation method it is characterised in that: concrete steps are such as
Under:
(1) α-ketoglutaric acid enzymatic conversion liquid and arginine fermentation liquid are inactivated through viable bacteria, adjusting ph with dilute hydrochloric acid is 4.0-4.5,
Enter microfiltration film separation system and carry out microfiltration, respectively obtain the α-ketoglutaric acid micro-filtrate removing thalline and arginine micro-filtrate；
Operation temperature is 10-50 DEG C, and entering film pressure with membrane pressure differential is 0.05-0.1mpa, and filter process adds purified water several times
Top is washed, until α-ketoglutaric acid and arginic content are less than shutdown after 2.0g/l in solution, obtains α-ketoglutaric acid micro-filtrate
With arginine micro-filtrate；
(2) the α-ketoglutaric acid micro-filtrate of step (1) gained clarification and arginine micro-filtrate are pumped into ultrafiltration membrane filter respectively,
Filter removing protein, its operating condition is ph 2-12, temperature 10-50 DEG C, operating pressure difference is 0.05-0.1mpa, obtains α -one penta
Diacid ultrafiltrate and arginine ultrafiltrate；
(3) by 732 cation exchange resiies on step (2) gained α-ketoglutaric acid ultrafiltrate, collect the α -one penta that ph is less than 2.0
Diacid effluent；732 cationic exchange resin adsorption on arginine filtrate, deionized water backwash after saturation to be adsorbed, it
Adopt the ammonia eluting of 3-8% afterwards, collect the arginine high flow point eluent that ph is 9-11, eluent obtains l- after deamination
Arginine solution；
(4) step (3) gained α-ketoglutaric acid effluent and l- arginine solution are mixed according to the ratio of mol ratio 1:1
Close, being adjusted to ph is 4.0 ± 0.5, obtains arginine-α-ketoglutaric acid mixed liquor；
(5) activated carbon decolorizing of 1.5-2.0%, temperature 60 are added in step (4) gained arginine-α-ketoglutaric acid mixed liquor
DEG C, stirring decolouring 25min, it is filtrated to get arginine-α-ketoglutaric acid mixing destaining solution；
(6) step (5) gained arginine-α-ketoglutaric acid mixing destaining solution is carried out being evaporated to the 12- of substance hydrops
18%, obtain arginine-α-ketoglutaric acid mixed concentrated liquid；
(7) step (6) gained arginine-α-ketoglutaric acid mixed concentrated liquid is spray-dried, is obtained final product target product.
3. l- arginine-α-ketoglutaric acid according to claim 2 preparation method it is characterised in that: described micro-filtration membrane
Piece-rate system adopts Middle hollow fiber membrane system, and microfiltration membrane aperture is 0.1um.
4. l- arginine-α-ketoglutaric acid according to claim 2 preparation method it is characterised in that: described ultrafilter membrane
Filter adopts Middle hollow fiber membrane system, and molecular cut off is 6000.
5. l- arginine-α-ketoglutaric acid according to claim 2 preparation method it is characterised in that: described micro-filtration membrane
Piece-rate system is Middle hollow fiber membrane system, and microfiltration membrane aperture is 0.1um.
6. l- arginine-α-ketoglutaric acid according to claim 2 preparation method it is characterised in that: described ultrafilter membrane
Filter adopts Middle hollow fiber membrane system, and molecular cut off is 6000.
7. l- arginine-α-ketoglutaric acid according to claim 2 preparation method it is characterised in that: described essence ammonia
Acid-α-ketoglutaric acid mixed liquor solution light transmittance after activated carbon decolorizing is more than 90%.
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Cited By (2)
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| CN111925305A (en) * | 2020-08-25 | 2020-11-13 | 精晶药业股份有限公司 | Method for preparing arginine ketoglutaric acid by spraying method |
| CN108220351B (en) * | 2017-12-19 | 2021-09-14 | 山东阳成生物科技有限公司 | Method for preparing L-arginine-alpha-ketoglutaric acid by biological enzyme method |
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