CN108690120A - A kind of method of bacillus production glycine histidyl lysine - Google Patents
A kind of method of bacillus production glycine histidyl lysine Download PDFInfo
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- CN108690120A CN108690120A CN201810504268.7A CN201810504268A CN108690120A CN 108690120 A CN108690120 A CN 108690120A CN 201810504268 A CN201810504268 A CN 201810504268A CN 108690120 A CN108690120 A CN 108690120A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P21/00—Preparation of peptides or proteins
- C12P21/02—Preparation of peptides or proteins having a known sequence of two or more amino acids, e.g. glutathione
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Abstract
The invention belongs to technical field of bioengineering, more particularly to a kind of method of bacillus production glycine histidyl lysine.The method of the production glycine histidyl lysine, it is characterized in that, it is inoculated into liquid seed culture medium and cultivates from picking bacillus on test tube slant, liquid seeds are made;Liquid seeds are inoculated into liquid fermentation medium, are fermented, zymotic fluid pH value is readjusted the distribution, aminoacids solution is added dropwise, continues to ferment, the zymotic fluid containing glycine histidyl lysine is made;By filtering fermentation liquor, filter liquor is collected, extractant is added into filter liquor, split-phase is made the extract liquor containing glycine histidyl lysine, extract liquor is evaporated in vacuo, and glycine histidyl lysine product is made.The serialization of glycine histidyl lysine production, scale may be implemented in the present invention;And the production technology of glycine histidyl lysine is easy, and production cost is relatively low, great industrial applications foreground.
Description
Technical field
The invention belongs to technical field of bioengineering, more particularly to a kind of bacillus produces glycine histidyl lysine
Method.
Background technology
Glycyl-L- histidyl-s-L-lysine (Glycyl-L-Histidyl-L-Lysine, GHK) is by glycine, group
A kind of tripeptides of propylhomoserin and lysine composition, molecular formula C14H24N6O4, molecular weight 340.38.Glycyl histidyl- relies ammonia
Acid can increase the survival rate of normal liver cell, and the synthesis of the DNA and RNA of cell cultured supernatant, be referred to as hepatocyte growth factor.
The complex compound (GHK-Cu) that GHK and GHK is formed with bivalent cupric ion can promote nerve cell, immunity-associated cell and glomerulus
Growth, division and the differentiation of cell, GHK-Cu can also promote or inhibit the conjunction of metalloproteinases in fibroblast cell culture
At.The multiple biological activities that GHK and GHK-Cu have make them have good application on including treatments such as dermatoplasty, burns
Foreground.
The production method of glycine histidyl lysine has extraction method and chemical synthesis.Extraction method is from the blood plasma of people
Extraction, this method by raw material sources due to being limited, without having the condition of large-scale production.Chemical synthesis is using sweet
Propylhomoserin, histidine and lysine synthesize to obtain GHK, such as thank into (fine-chemical intermediate, 2008.6) and use solid-phase synthesis
GHK, product yield 79.4% are synthesized;As Peng's small third (Chinese biological chemistry and molecular biosciences journal, 2003.3) uses
Liquid phase synthesizing method has synthesized GHK;As 101230089 A (application number 200810043144.X) of Chinese patent literature CN are disclosed
A kind of solid phase synthesis process of glycine histidyl lysine, the synthesis of GHK are to pass through four at 45 DEG C~50 DEG C in a solvent
Step reaction is made.But the severeer environmental issue of chemical synthesis generally existing, reaction condition is generally relatively violent, to equipment requirement
Higher, production technology is complicated, and product yield is low;And due to the residual containing substances such as raw material, by-product, solvents in product
Object, therefore the GHK that this method obtains can not be applied directly in pharmaceuticals industry.
With the increasingly raising that people require green product, there is production using the method that biotechnology produces GHK
Product green natural, the advantages that safe and reliable, reaction condition is mild, environmental pollution is small and be valued by people.Bioanalysis and change
It learns synthetic method to compare, with raw material sources are extensive, by-product is few, product yield is high, production cost is low, are easily industrialized life
The characteristics of production is the GHK production methods that there are industrialization prospect in a kind of economical and effective and pole.
Invention content
In order to compensate for the shortcomings of the prior art, the present invention provides a kind of bacillus to produce glycine histidyl lysine
Method.
The present invention is achieved through the following technical solutions:
A kind of method of bacillus production glycine histidyl lysine, includes the following steps:
(1) be inoculated into liquid seed culture medium from 1~2 ring bacillus of picking on test tube slant, 28~30 DEG C,
Under 120~160r/min, 16~20h is cultivated, liquid seeds are made;
(2) liquid seeds are inoculated into for 3~5% inoculum concentration in liquid fermentation medium by volume, fermentation 20~
For 24 hours, zymotic fluid pH value 7.5~8.5 is readjusted the distribution, aminoacids solution is added dropwise, continues 72~96h of fermentation, is made and relies containing glycyl histidyl-
The zymotic fluid of propylhomoserin;
(3) by zymotic fluid filtering with microporous membrane, filter liquor is collected, extractant is added into filter liquor, be uniformly mixed, it is quiet
Split-phase is set, the extract liquor containing glycine histidyl lysine is made, extract liquor is evaporated in vacuo, glycyl histidyl- is made and relies
Propylhomoserin product.
The present invention more excellent scheme be:
In step (1), bacillus is bacillus subtilis (Bacillus subtilis) ATCC6633, which protects
It is hidden in American Type Culture collection (ATCC), can be obtained by way of purchase.
In step (1), the group of liquid seed culture medium is divided into:10~20.0g/L of glucose, 5~10.0g/L of peptone,
5.0~10.0g/L of beef extract, glycine histidyl lysine 1.0g/L, NaCl 1.0~3.0g/L, pH 7.0.
In step (2), the group of liquid fermentation medium is divided into:30.0~50.0g/L of glucose, peptone 5.0g/L, ox
Meat extract 5.0g/L, glycyl histidine 1.0g/L, lysine 1.0g/L, K2HPO44.0g/L, MgSO41.0g/L, pH7.2.
In step (2), the fermentation condition of liquid seeds is 28~37 DEG C, 150~200r/min.
In step (2), the sodium hydroxide solution that zymotic fluid pH value uses mass percentage concentration as 10~20wt% is readjusted the distribution.
In step (2), the dosage of aminoacids solution be fermentating liquid volume than 20~30%, when the stopping of aminoacids solution is added dropwise
Between for 8h before fermentation ends.The group of aminoacids solution is divided into:20~50mmol/L of glycine, 20~50mmol/L of histidine rely ammonia
Acid 50~80mmol/L, glycyl histidine 20~40mmol/L, MgC1220~30mmol/L, pH8.0.
In step (3), the operating pressure of miillpore filter is 0.05~0.1MPa, and the aperture of miillpore filter is 0.2~0.4 μ
m。
In step (3), extractant be ethyl acetate or butyl acetate, dosage be filtrate volume percentage 30~
50%.
Beneficial effects of the present invention are as follows:The bacillus that the present invention uses can be by the sweet ammonia of Amino acid synthesis in zymotic fluid
Acyl histidyl- lysine and production rate height;The glycine histidyl lysine production method of the present invention meets relevant food safety law
Rule, safe and non-toxic;The serialization of glycine histidyl lysine production, scale, and glycyl may be implemented in the present invention
The production technology of histidyl- lysine is easy, and production cost is relatively low, great industrial applications foreground.
Specific implementation mode
Technical scheme of the present invention is specifically described or is described further with reference to embodiment, it is therefore intended that more
The method of the present invention, but protection scope of the present invention embodiment not limited to the following are understood well.
The determination step of glycine histidyl lysine content is as follows in the present invention:
The methyl orange standard items for weighing 32.733mg are dissolved in 1000mL deionized waters, are shaken up, and are made a concentration of
0.1mmol/L methyl orange standard solution.
Weigh 34.04mg, 51.06mg, 68.08mg, 85.10mg, 102.12mg, 119.14mg, 136.16mg,
The glycine histidyl lysine standard items of 153.18mg are dissolved in respectively in 1000mL deionized waters, are shaken up, and GHK solution is made,
Above-mentioned GHK solution is diluted 10 times respectively, the GHK standard solution of 0.01~0.045mmol/L is made.
8 parts of methyl orange standard solution, every part of each 2.0mL is taken to be separately added into sodium dihydrogen phosphate-citric acid solution
2.0mL, then the GHK standard solution 2.0mL of various concentration are separately added into, it is sufficiently mixed, is heated to 30 DEG C, acutely shake, constant temperature
React 30min;4000r/min, centrifugation 15min, take supernatant 1.0mL, shake up respectively.After the reaction was complete, pass through chemistry
Reaction equation can obtain remaining methyl orange molar concentration value in standard reaction liquid.With spectrophotometer in 465nm wavelength
Place measures the absorbance value of each standard reaction liquid, is remaining methyl orange in ordinate, standard reaction liquid with absorbance value (A)
Molar concentration value (C) is abscissa, makes methyl orange solution standard curve.The regression equation of the curve is obtained according to standard curve
For:A=8.978C-0.021 (R2=0.999), wherein:A is absorbance value, and C is methyl orange molar concentration (mmol/L), R2For
Related coefficient.The variation of absorbance value A and methyl orange molar concentration are linear, and degree of fitting is up to 0.999.
It weighs GHK samples 34.04mg to be measured to be dissolved in 1000mL deionized waters, GHK sample solutions to be measured is made, then should
Solution dilutes 10 times, and the GHK sample solutions to be measured of a concentration of 0.01mmol/L are made.Methyl orange standard solution 2.0mL is taken, is added
Sodium dihydrogen phosphate-citric acid solution 2.0mL adds GHK sample solutions 2.0mL to be measured and is reacted, waited for after reaction
Absorbance value of the reaction solution through spectrophotometer detection reaction solution at 465nm wavelength is surveyed, according to methyl orange solution mark obtained
Then directrix curve, remaining methyl orange molar concentration after being reacted calculate the molar concentration of GHK according to following formula:
React the molar concentration of the preceding methyl orange standard solution of methyl orange molar concentration (mmol/L)=reaction of consumption
(mmol/L) remaining methyl orange molar concentration (mmol/L) after-reaction
Methyl orange molar concentration (mmol/L) ÷ 2 of GHK molar concentrations (mmol/L)=reaction consumption
GHK mass is calculated according to following formula:GHK mass (mg)=340.38 × GHK molar concentrations × liquor capacity
GHK contents are calculated according to following formula:GHK contents (%)=(GHK mass ÷ GHK sample qualities to be measured) ×
100%.
Raw material sources:Glycine, histidine, lysine are purchased from the Shandong bio tech ltd Xi Tang, glycyl group ammonia
Acid is purchased from the Shanghai bio tech ltd Yuan Ye, and ethyl acetate, butyl acetate are purchased from the Shanghai bio tech ltd Pu Zhen,
Methyl orange standard items are purchased from Tianjin Kai Tong chemical reagent Co., Ltd;Glycine histidyl lysine standard items are given birth to purchased from gill
Change (Shanghai) Co., Ltd..
Embodiment 1
A kind of method of bacillus production glycine histidyl lysine, includes the following steps:
(1) be inoculated into the liquid seed culture medium of 10mL from 2 ring bacillus of picking on test tube slant, 30 DEG C,
Under 160r/min, 20h is cultivated, liquid seeds are made.
(2) liquid seeds are inoculated into for 5% inoculum concentration in the liquid fermentation medium of 200mL by volume, 37
DEG C, ferment for 24 hours under 200r/min, readjust the distribution zymotic fluid pH value 8.0, be added dropwise aminoacids solution, dosage be fermentating liquid volume than 30%,
Continue the 96h that ferments, the zymotic fluid containing glycine histidyl lysine is made.
(3) filtering with microporous membrane for being 0.2 μm with aperture at 0.1MPa by zymotic fluid collects filter liquor.To filter liquor
Middle addition ethyl acetate, the dosage of ethyl acetate are the 50% of filtrate volume percentage,
Be uniformly mixed, stand split-phase, be made the extract liquor containing glycine histidyl lysine, by extract liquor 100 DEG C,
It is evaporated under 667Pa, glycine histidyl lysine product 5.07g is made.
Bacillus in the step (1) is bacillus subtilis (Bacillus subtilis) ATCC6633, the bacterium
Kind is purchased from American Type Culture collection (ATCC).
Liquid seed culture medium group in the step (1) is divided into:Glucose 20.0g/L, peptone 10.0g/L, beef
Cream 10.0g/L, glycine histidyl lysine 1.0g/L, NaCl 3.0g/L, pH 7.0.
Fluid nutrient medium group in the step (2) is divided into:Glucose 50.0g/L, peptone 5.0g/L, beef extract
5.0g/L, glycyl histidine 1.0g/L, lysine 1.0g/L, K2HPO44.0g/L, MgSO41.0g/L, pH7.2.
Aminoacids solution group in the step (2) is divided into:Glycine 50mmol/L, histidine 50mmol/L, lysine
80mmol/L, glycyl histidine 40mmol/L, MgC1230mmol/L, pH8.0.
Embodiment 2
A kind of method of bacillus production glycine histidyl lysine, includes the following steps:
(1) be inoculated into the liquid seed culture medium of 10mL from 1 ring bacillus of picking on test tube slant, 28 DEG C,
Under 120r/min, 16h is cultivated, liquid seeds are made.
(2) liquid seeds are inoculated into for 3% inoculum concentration in the liquid fermentation medium of 200mL by volume, 28
DEG C, ferment under 150r/min 20h, readjusts the distribution zymotic fluid pH value 7.5, be added dropwise aminoacids solution, dosage be fermentating liquid volume than 20%,
Continue the 72h that ferments, the zymotic fluid containing glycine histidyl lysine is made.
(3) filtering with microporous membrane for being 0.4 μm with aperture at 0.05MPa by zymotic fluid collects filter liquor.To filter liquor
Middle addition ethyl acetate, the dosage of ethyl acetate are the 30% of filtrate volume percentage, are uniformly mixed, stand split-phase, are made
Extract liquor containing glycine histidyl lysine evaporates extract liquor at 100 DEG C, 667Pa, and glycyl histidyl- is made and relies
Propylhomoserin product 3.03g.
Bacillus in the step (1) is bacillus subtilis (Bacillus subtilis) ATCC6633, the bacterium
Kind is purchased from American Type Culture collection (ATCC).
Liquid seed culture medium group in the step (1) is divided into:Glucose 10.0g/L, peptone 5.0g/L, beef extract
5.0g/L, glycine histidyl lysine 1.0g/L, NaCl 1.0g/L, pH 7.0.
Fluid nutrient medium group in the step (2) is divided into:Glucose 30.0g/L, peptone 5.0g/L, beef extract
5.0g/L, glycyl histidine 1.0g/L, lysine 1.0g/L, K2HPO44.0g/L, MgSO41.0g/L, pH7.2.
Aminoacids solution group in the step (2) is divided into:Glycine 20mmol/L, histidine 20mmol/L, lysine
50mmol/L, glycyl histidine 20mmol/L, MgC1220mmol/L, pH8.0.
Embodiment 3
The method of bacillus production glycine histidyl lysine as described in Example 1, the difference is that:
In step (2), the dosage of aminoacids solution be fermentating liquid volume than 25%.
Glycine histidyl lysine product 4.22g is made with this condition.
Embodiment 4
The method of bacillus production glycine histidyl lysine as described in Example 1, the difference is that:
In step (3), butyl acetate is added into filter liquor, the dosage of butyl acetate is filtrate volume percentage
50%.
Glycine histidyl lysine product 5.01g is made with this condition.
Claims (9)
1. a kind of method of bacillus production glycine histidyl lysine, it is characterized in that, include the following steps:(1) from examination
1~2 ring bacillus of picking is inoculated into liquid seed culture medium on pipe inclined-plane, at 28~30 DEG C, 120~160r/min,
16~20h is cultivated, liquid seeds are made;(2) liquid seeds are inoculated into liquid fermentation for 3~5% inoculum concentration by volume
In culture medium, fermentation 20~for 24 hours, zymotic fluid pH value 7.5~8.5 is readjusted the distribution, aminoacids solution is added dropwise, continues 72~96h of fermentation, is made and contains
There is the zymotic fluid of glycine histidyl lysine;(3) by zymotic fluid filtering with microporous membrane, filter liquor is collected, into filter liquor
Extractant is added, is uniformly mixed, stands split-phase, the extract liquor containing glycine histidyl lysine is made, by extract liquor vacuum
Glycine histidyl lysine product is made in evaporation.
2. the method for bacillus production glycine histidyl lysine according to claim 1, which is characterized in that step
(1) in, bacillus is bacillus subtilis (Bacillus subtilis) ATCC6633.
3. the method for bacillus production glycine histidyl lysine according to claim 1, which is characterized in that step
(1) in, the group of liquid seed culture medium is divided into:10~20.0g/L of glucose, 5~10.0g/L of peptone, beef extract 5.0~
10.0g/L, glycine histidyl lysine 1.0g/L, NaCl 1.0~3.0g/L, pH 7.0.
4. the method for bacillus production glycine histidyl lysine according to claim 1, which is characterized in that step
(2) in, the group of liquid fermentation medium is divided into:30.0~50.0g/L of glucose, peptone 5.0g/L, beef extract 5.0g/L are sweet
Aminoacyl histidine 1.0g/L, lysine 1.0g/L, K2HPO44.0g/L, MgSO41.0g/L, pH7.2.
5. the method for bacillus production glycine histidyl lysine according to claim 1, which is characterized in that step
(2) in, the fermentation condition of liquid seeds is 28~37 DEG C, 150~200r/min.
6. the method for bacillus production glycine histidyl lysine according to claim 1, which is characterized in that step
(2) in, the sodium hydroxide solution that zymotic fluid pH value uses mass percentage concentration as 10~20wt% is readjusted the distribution.
7. the method for bacillus production glycine histidyl lysine according to claim 1, which is characterized in that step
(2) in, the dosage of aminoacids solution be fermentating liquid volume than 20~30%, the dwell time that aminoacids solution is added dropwise is fermentation ends
Preceding 8h.The group of aminoacids solution is divided into:20~50mmol/L of glycine, 20~50mmol/L of histidine, 50~80mmol/ of lysine
L, glycyl histidine 20~40mmol/L, MgC1220~30mmol/L, pH8.0.
8. the method for bacillus production glycine histidyl lysine according to claim 1, which is characterized in that step
(3) in, the operating pressure of miillpore filter is 0.05~0.1MPa, and the aperture of miillpore filter is 0.2~0.4 μm.
9. the method for bacillus production glycine histidyl lysine according to claim 1, which is characterized in that step
(3) in, extractant is ethyl acetate or butyl acetate, and dosage is the 30~50% of filtrate volume percentage.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109988304A (en) * | 2019-04-22 | 2019-07-09 | 苏州美瑞姿生物科技有限公司 | The synthetic method of the poly-aspartate derivant of glycine histidyl lysine grafting |
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| CN101245363A (en) * | 2008-03-14 | 2008-08-20 | 南京华锦生物制品有限公司 | Production fermentation technique for glutathione |
| CN103344592A (en) * | 2013-07-18 | 2013-10-09 | 齐鲁工业大学 | Determining method for GHK (Glycyl-L-Histidyl-L-Lysine) content |
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2018
- 2018-05-23 CN CN201810504268.7A patent/CN108690120A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101245363A (en) * | 2008-03-14 | 2008-08-20 | 南京华锦生物制品有限公司 | Production fermentation technique for glutathione |
| CN103344592A (en) * | 2013-07-18 | 2013-10-09 | 齐鲁工业大学 | Determining method for GHK (Glycyl-L-Histidyl-L-Lysine) content |
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| LIAKOPOULOU K.M.等: "A new synthesis of the tripeptide Gly-His-Lys with antimicrobial activity.", 《AMINO ACIDS》 * |
| 彭小三等: "甘氨酰组氨酰赖氨酸(GHK)的液相合成及其酶促降解", 《中国生物化学与分子生物学报》 * |
| 马丽等: "固相法合成Arg-Leu-Pro三肽", 《应用化学》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109988304A (en) * | 2019-04-22 | 2019-07-09 | 苏州美瑞姿生物科技有限公司 | The synthetic method of the poly-aspartate derivant of glycine histidyl lysine grafting |
| CN109988304B (en) * | 2019-04-22 | 2021-06-08 | 苏州美瑞姿生物科技有限公司 | Synthesis method of glycyl histidyl lysine grafted polyaspartic acid derivative |
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