CN106278954A - A kind of method extracting agmatine - Google Patents
A kind of method extracting agmatine Download PDFInfo
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- CN106278954A CN106278954A CN201610684104.8A CN201610684104A CN106278954A CN 106278954 A CN106278954 A CN 106278954A CN 201610684104 A CN201610684104 A CN 201610684104A CN 106278954 A CN106278954 A CN 106278954A
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- agmatine
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- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
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- C—CHEMISTRY; METALLURGY
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
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Abstract
The invention discloses a kind of method extracting agmatine, relate to the extractive technique field of compound.Comprise the following steps: (1) uses raw material to be arginine, and the bioenzymatic conversion feed liquid containing agmatine produced under arginine decarboxylase effect carries out freeze thawing treatment, makes arginine decarboxylase lose biological activity；(2) take the bioenzymatic conversion feed liquid after inactivation and carry out high speed centrifugation, isolate thalline and protein matter, obtain centrifugal clear liquid；(3) centrifugal clear liquid is crossed membranous system, remove thalline relic and macromolecular substances, obtained film dialysis clear liquid；(4) concentrate crossing film dialysis clear liquid, regulate pH after activated carbon decolorizing and carry out solvent crystal, filter to obtain agmatine crude product.This method can quickly process acquisition agmatine crude product, decreases chemical reaction intermediate processing steps, decreases impurity in product, simultaneously, capacity efficiency is high, and low cost is easy and simple to handle, good product quality, improves product quality and yield, creates good economic benefit.
Description
Technical field
The present invention relates to the extractive technique field of compound.
Background technology
Agmatine (gamatine) is the material of a multi-biological function, discharges hypothalamic hormone by stimulating
Carry out work, it is possible to promoting Alfasone and growth hormone, agmatine has multiple benefits, it is possible to increase health durability degree, to motion
Member and bodybuilders have certain benefit and it can be made satisfied, can accelerate physical recovery simultaneously, improve muscle quantities, reduce obesity
Oils and fats, improves health performance, and to pursuing, health is dynamic and to seek each age level healthy lifestyles helpful, guanidine
Base butylamine can also improve nitric oxide production content by two kinds of approach, stimulates release nitric oxide and suppression Nitric oxide syntheses
Synthesis (Nitric oxide syntheses can consume nitric oxide).
Having data to show, central nervous system, gamatine can strengthen the analgesic effect of opioid drug, slow down drug resistance
The generation of property and improve Acute Morphine withdrawal syndrome, gamatine can also promote consolidation of memory in addition.At cardiovascular system,
Gamatine can reduce heart rate, and mean arterial pressure, left chamber pressure, peripheral vascular resistance and cardiac index etc., gamatine is also simultaneously
Gastric acid and pepsic secretion can be increased, make mucosal thickness thinning, deteriorate the mucosa infection etc. that stress cause.There is research simultaneously
Showing, agmatine also has the effect of clear and definite suppression tumor cell proliferation, and the effect of its suppression tumor cell proliferation has tumor
Cell strain specificity.
Present stage, main by chemical synthesis acquisition gamatine on market, primary raw material has Putriscine, O-first
Base isourea sulfate, sulphuric acid, alcohol etc., course of reaction energy consumption is high, and yield is low, and impurity is many, and potential safety hazard is big, has certain dirt to environment
Dye；Also have employing Isosorbide-5-Nitrae-dibromobutane and potassium phthalimide is raw material simultaneously, is substituted, amine solution and guanidinated three steps
Reaction prepares the report of agmatine sulfate, this route reaction mild condition, but side reaction is more, and complex operation, and abnormal smells from the patient is difficult
Hearing, course of reaction uses relatively multi-solvent, does not meets the Production requirement of clean and effective.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of method extracting agmatine, and the method can quickly process and obtain
Obtain agmatine crude product, relatively conventional chemical synthesis, effectively reduce chemical reaction intermediate processing steps, decrease intermediate
Side reaction and during impurity, useless solvent, the generation of waste gas, meanwhile, capacity efficiency is high, and low cost is easy and simple to handle, product matter
Measure, decrease impurity in product, improve product quality and yield, create good economic benefit.
For solving above-mentioned technical problem, the technical solution used in the present invention is: a kind of method extracting agmatine, including
Following steps:
(1) using raw material is arginine, in the lower generation of arginine decarboxylase (arginine decarboxylase, ADC) effect
The bioenzymatic conversion feed liquid containing agmatine carry out freeze thawing treatment, make arginine decarboxylase lose biological activity；
(2) take the bioenzymatic conversion feed liquid after inactivation and carry out high speed centrifugation, isolate thalline and protein matter, obtain centrifugal clear
Liquid；
(3) centrifugal clear liquid is crossed membranous system, remove thalline relic and macromolecular substances, obtained film dialysis clear liquid；
(4) by cross film dialysis clear liquid concentrate, after activated carbon decolorizing regulate pH carry out solvent crystal, filter agmatine is thick
Product.
Preferably, in step (1), arginine decarboxylase is the arginine decarboxylase from antibacterial or plant-derived smart ammonia
Acid decarboxylase.
Preferably, in step (1), freeze thawing treatment, use-20 DEG C～5 DEG C ,-30 DEG C～10 DEG C ,-35 DEG C～20 DEG C successively
Freeze thawing treatment scheme.
It is further preferred that in step (1), freeze thawing treatment, use the mode of filtration to isolate portion after dissolving for the first time
Divide thalline.
Preferably, in step (2), take after the bioenzymatic conversion feed liquid after inactivation adds chelating agent or flocculant, carry out from
The heart.
It is further preferred that chelating agent used or flocculant have: mercaptoethylmaine, polyacrylamide, TGA, thiourea or
EDTA(ethylenediaminetetraacetic acid).
Preferably, in step (2), high speed centrifugation uses disk centrifugal separator or tube centrifuge, centrifugal rotational speed 12000～
15000 revs/min.
Preferably, in step (2), high speed centrifugation uses stacked centrifuge, and centrifugal rotational speed is at 15000 revs/min.
Preferably, in step (3), membranous system is pottery filter membrane and ultrafilter membrane.
It is further preferred that in step (3), pottery filter sizes is 20-100 μm；Ultrafiltration uses two-stage ultrafiltering, one-level fenestra
Footpath 8000-10000 dalton, secondary membrane aperture 3000-5000 dalton.
In step (3), ultrafiltration, secondary membrane aperture can also be 1500-3000 dalton；
Obtain film dialysis clear liquid after two-stage ultrafiltering, cross film dialysis clear liquid light transmittance more than 97%.
Preferably, in step (4), pH is 3.0-7.0.
Preferably, in step (4), after film dialysis clear liquid was concentrated into the 20-50% of film dialysis clear liquid original volume excessively, add
Enter the medicinal carbon of agmatine quality 0.5%-3% in film dialysis clear liquid and carry out adsorption bleaching.
Preferably, in step (4), solvent is methanol, ethanol or isopropanol, and solvent consumption is that the film of crossing after regulation pH is dialysed
1.2-4.5 times of supernatant volume.
Use and have the beneficial effects that produced by technique scheme: the inventive method can quickly process acquisition agmatine
Crude product, relatively conventional chemical synthesis, effectively reduce chemical reaction intermediate processing steps, decrease intermediate side reaction and
During impurity, useless solvent, the generation of waste gas, meanwhile, capacity efficiency is high, and low cost is easy and simple to handle, good product quality, subtracts
Lack impurity in product, improve product quality and yield, create good economic benefit.
Detailed description of the invention
Below in conjunction with detailed description of the invention, the present invention is further detailed explanation.
Embodiment 1
(1) using raw material is arginine, arginine decarboxylase (arginine decarboxylase is the arginine decarboxylase from antibacterial)
Lower bioenzymatic conversion feed liquid 500L containing agmatine 105kg produced of effect is placed in freeze dryer distributor pipe, carries out at freeze thawing
Reason, fast cooling is incubated 1 hour to-20 DEG C, is rapidly heated to 5 DEG C, is directly placed in centrifuge by the liquid in distributor pipe, gets rid of
Filter cutting out partial thalline；Liquid rejection filter gone out the most averagely imports in freeze dryer distributor pipe, fast cooling to-30 DEG C of insulations
It is warming up to 10 DEG C after 1 hour again, is cooled to-35 DEG C in the same way and rises again again to 20 DEG C.
(2) the bioenzymatic conversion feed liquid (freeze thawing inactivation) that will rise again, adds the chelating agent of bioenzymatic conversion feed liquid quality 2%,
Slowly putting into disk centrifugal separator after stirring 1 hour, centrifugal rotational speed, at 12000～15000 revs/min, is isolated thalline, is adopted continuously
Go out clear liquid, obtain centrifugal clear liquid 470L.
(3) above-mentioned clear liquid 470L carries out pottery filter, and pottery filter sizes is 20-100 μm；Ultrafiltration uses two-stage ultrafiltering, one-level
Membrane aperture 8000-10000 dalton, secondary membrane aperture 3000-5000 dalton, two-stage ultrafiltering, after terminating, use 50L purified water
Washing membranous system, obtained film dialysis clear liquid 500L, detected agmatine content 193g/L, yield 92.3%, crossed film dialysis clear liquid printing opacity
Rate is more than 97%.
(4) take above-mentioned cross film dialysis clear liquid 500L be concentrated into film dialysis clear liquid original volume 50% after, add 3kg activity
Charcoal adsorption bleaching, after filtration, regulates pH to 5.0, adds 500L isopropanol and separates out crystal, filter to obtain agmatine in gained feed liquid
Crude product, 65 DEG C of vacuum is dried, detects moisture 0.26%, pure 90.22kg, yield 93.5%.
Embodiment 2
(1) using raw material is arginine, and at arginine decarboxylase, (arginine decarboxylase is from plant-derived arginine decarboxylation
Enzyme) act on and descend the bioenzymatic conversion feed liquid containing agmatine produced to carry out freeze thawing treatment, make arginine decarboxylase lose biology
Activity.Freeze dryer distributor pipe 80 is cooled to-20 DEG C, in every distributor pipe, adds 5L bioenzymatic conversion feed liquid, constant temperature-20
DEG C insulation 1 hour, be rapidly heated to 5 DEG C, the liquid in distributor pipe be directly placed in centrifuge, rejection filter cutting out partial thalline
Amount to 4.6kg；Liquid rejection filter gone out the most averagely imports in distributor pipe, and fast cooling heats up after being incubated 1 hour to-30 DEG C again
To 10 DEG C, be cooled to-35 DEG C in the same way and rise again again to 20 DEG C.
(2) the bioenzymatic conversion feed liquid (freeze thawing inactivation) that will rise again, the bioenzymatic conversion feed liquid quality 3% that addition is risen again
Chelating agent, slowly puts into disk centrifugal separator after stirring 1 hour, and centrifugal rotational speed, at 12000～15000 revs/min, isolates bacterium
Body, continuous extraction clear liquid, obtain centrifugal clear liquid 355L.
(3) above-mentioned clear liquid 355L carries out pottery filter, and pottery filter sizes is 20-100 μm；Ultrafiltration uses two-stage ultrafiltering, one-level
Membrane aperture 8000-10000 dalton, secondary membrane aperture 3000-5000 dalton, two-stage ultrafiltering, after terminating, use 50L purified water
Washing membranous system, obtained film dialysis clear liquid 400L, detected agmatine content 190.2g/L, yield 90.5%, crossed film dialysis clear liquid saturating
Light rate is more than 97%.
(4) take the above-mentioned film dialysis clear liquid 400L that crosses and be concentrated into the 40% of film dialysis clear liquid original volume, add 2kg activated carbon
Adsorption bleaching, after filtration, regulates pH to 6.0, and the ethanol 500L adding volume fraction 95% in gained feed liquid separates out crystal, mistake
Filter to obtain agmatine crude product, pure 69.3kg, yield 91.2%.
Embodiment 3
(1) using raw material is arginine, arginine decarboxylase (arginine decarboxylase is the arginine decarboxylase from antibacterial)
Lower bioenzymatic conversion feed liquid 800L containing agmatine produced of effect is placed in freeze dryer distributor pipe, carries out freeze thawing treatment, soon
Speed is cooled to-20 DEG C and is incubated 1 hour, is rapidly heated to 5 DEG C, is directly placed in centrifuge by the liquid in distributor pipe, and rejection filter is divided
Separate out part thalline；Liquid rejection filter gone out the most averagely imports in distributor pipe, fast cooling to-30 DEG C insulation 1 hour after again
It is warming up to 10 DEG C, is cooled to-35 DEG C in the same way and rises again again to 20 DEG C.
(2) the bioenzymatic conversion feed liquid (freeze thawing inactivation) that will rise again, adds the bioenzymatic conversion feed liquid quality 2.5% risen again
Flocculant, slowly put into tube centrifuge after stirring 1 hour, centrifugal rotational speed, at 12000～15000 revs/min, isolates bacterium
Body, continuous extraction clear liquid, obtain centrifugal clear liquid 760L.
(3) above-mentioned centrifugal clear liquid 760L carries out pottery filter, and pottery filter sizes is 20-100 μm；Ultrafiltration uses two-stage ultrafiltering,
One-level membrane aperture 8000-10000 dalton, secondary membrane aperture 3000-5000 dalton, two-stage ultrafiltering is after terminating, pure with 50L
Change water washing membranous system, obtained film dialysis clear liquid 805L, and detected agmatine content 184.34g/L, yield 92.3%, and crossed film dialysis
Clear liquid light transmittance is more than 97%.
(4) take the above-mentioned film dialysis clear liquid 400L that crosses and be concentrated into the 50% of film dialysis clear liquid original volume, add 2kg activated carbon
Adsorption bleaching, after filtration, regulates pH to 4.5, and the ethanol 500L adding volume fraction 95% in gained feed liquid separates out crystal, mistake
Filtering to obtain agmatine crude product, 60 DEG C of vacuum is dried, detects moisture 0.3%, obtains the pure 67.1kg of agmatine crude product, yield 91.0%.
Claims (10)
1. the method extracting agmatine, it is characterised in that: comprise the following steps:
(1) using raw material is arginine, the bioenzymatic conversion feed liquid containing agmatine produced under arginine decarboxylase effect
Carry out freeze thawing treatment, make arginine decarboxylase lose biological activity；
(2) take the bioenzymatic conversion feed liquid after inactivation and carry out high speed centrifugation, isolate thalline and protein matter, obtain centrifugal clear
Liquid；
(3) centrifugal clear liquid is crossed membranous system, remove thalline relic and macromolecular substances, obtained film dialysis clear liquid；
(4) by cross film dialysis clear liquid concentrate, after activated carbon decolorizing regulate pH carry out solvent crystal, filter agmatine is thick
Product.
A kind of method extracting agmatine the most according to claim 1, it is characterised in that: in step (1), arginine decarboxylation
Enzyme is the arginine decarboxylase from antibacterial or plant-derived arginine decarboxylase.
A kind of method extracting agmatine the most according to claim 1, it is characterised in that: in step (1), freeze thawing treatment,
Use-20 DEG C～5 DEG C ,-30 DEG C～the freeze thawing treatment scheme of 10 DEG C ,-35 DEG C～20 DEG C successively.
A kind of method extracting agmatine the most according to claim 3, it is characterised in that: in step (1), freeze thawing treatment,
The mode cutting out partial thalline of filtration is used after dissolving for the first time.
A kind of method extracting agmatine the most according to claim 1, it is characterised in that: in step (2), after taking inactivation
After bioenzymatic conversion feed liquid adds chelating agent or flocculant, it is centrifuged.
A kind of method extracting agmatine the most according to claim 1, it is characterised in that: in step (2), high speed centrifugation is adopted
With disk centrifugal separator or tube centrifuge, centrifugal rotational speed is at 12000～15000 revs/min.
A kind of method extracting agmatine the most according to claim 1, it is characterised in that: in step (3), membranous system is pottery
Filter membrane and ultrafilter membrane.
A kind of method extracting agmatine the most according to claim 7, it is characterised in that: in step (3), filter sizes of making pottery
For 20-100 μm；Ultrafiltration uses two-stage ultrafiltering, one-level membrane aperture 8000-10000 dalton, 3000-5000 road, secondary membrane aperture
Er Dun.
A kind of method extracting agmatine the most according to claim 1, it is characterised in that in step (4), pH is 3.0-
7.0。
A kind of method extracting agmatine the most according to claim 1, it is characterised in that in step (4), solvent is first
Alcohol, ethanol or isopropanol.
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| CN201610684104.8A CN106278954B (en) | 2016-08-18 | 2016-08-18 | A kind of method for extracting agmatine |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114058651A (en) * | 2021-09-30 | 2022-02-18 | 新泰市佳禾生物科技有限公司 | Preparation method of agmatine |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1260588A2 (en) * | 2001-05-25 | 2002-11-27 | Ajinomoto Co., Ltd. | Methods of producing agmatine and arginine decarboxylase |
| EP1270552A2 (en) * | 2001-05-25 | 2003-01-02 | Ajinomoto Co., Inc. | Production process for a guanidine derivative containing an amido group and for a salt thereof |
| CN104152478A (en) * | 2014-07-31 | 2014-11-19 | 洛阳华荣生物技术有限公司 | Method for coproducing D-arginine and gamatine through biotransformation |
| CN105861529A (en) * | 2016-05-27 | 2016-08-17 | 江南大学 | Arginine decarboxylase and application thereof |
-
2016
- 2016-08-18 CN CN201610684104.8A patent/CN106278954B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1260588A2 (en) * | 2001-05-25 | 2002-11-27 | Ajinomoto Co., Ltd. | Methods of producing agmatine and arginine decarboxylase |
| EP1270552A2 (en) * | 2001-05-25 | 2003-01-02 | Ajinomoto Co., Inc. | Production process for a guanidine derivative containing an amido group and for a salt thereof |
| CN104152478A (en) * | 2014-07-31 | 2014-11-19 | 洛阳华荣生物技术有限公司 | Method for coproducing D-arginine and gamatine through biotransformation |
| CN105861529A (en) * | 2016-05-27 | 2016-08-17 | 江南大学 | Arginine decarboxylase and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| SUN XIA等: ""Enzymatic production of agmatine by recombinant arginine decarboxylase"", 《JOURNAL OF MOLECULAR CATALYSIS B: ENZYMATIC》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114058651A (en) * | 2021-09-30 | 2022-02-18 | 新泰市佳禾生物科技有限公司 | Preparation method of agmatine |
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