CN105087509A - Preparation method of lauric acid modified superoxide dismutase - Google Patents
Preparation method of lauric acid modified superoxide dismutase Download PDFInfo
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- CN105087509A CN105087509A CN201510535250.XA CN201510535250A CN105087509A CN 105087509 A CN105087509 A CN 105087509A CN 201510535250 A CN201510535250 A CN 201510535250A CN 105087509 A CN105087509 A CN 105087509A
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0089—Oxidoreductases (1.) acting on superoxide as acceptor (1.15)
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- C12Y115/00—Oxidoreductases acting on superoxide as acceptor (1.15)
- C12Y115/01—Oxidoreductases acting on superoxide as acceptor (1.15) with NAD or NADP as acceptor (1.15.1)
- C12Y115/01001—Superoxide dismutase (1.15.1.1)
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Abstract
The invention discloses a preparation method of lauric acid modified superoxide dismutase. The preparation method includes subjecting raw materials including lauric acid and thionyl chloride to pyridine DMF (dimethyl formamide) catalytic reaction to obtain lauroyl chloride; subjecting the lauroyl chloride and superoxide dismutase to acylation reaction at the temperature of 40-48 DEG C under alkaline conditions; filtering an acylation reactant, taking supernatant I, and subjecting the supernatant I to temperature gradient treatment of stages 3-6, wherein the initial temperature is 40-45 DEG C, temperature difference of each stage is 5-10 DEG C, the low temperature of last stage treatment is 5-10 DEG C, and the cooling temperature of previous stage treatment is recovered after cooling of each stage treatment; taking supernatant obtained after temperature gradient treatment, and subjecting the supernatant to stage-2 sediment sterilization and purification to obtain the lauric acid modified superoxide dismutase. The preparation method has the advantages of high activity and yield of the lauric acid modified superoxide dismutase obtained according to the method, simple process and short period.
Description
Technical field
The present invention relates to a kind of superoxide-dismutase modification technique, particularly relate to a kind of preparation method of La-SOD.
Background technology
Superoxide-dismutase (SOD) due to be subject to transformation period short, relative molecular mass greatly, not easily permeate through cell membranes, oral time be subject to the restriction of the factors such as stomach en-decomposition, body internal specific, SOD be difficult to as medicinal enzyme be widely used in clinical in.Chemically modified is carried out to SOD, the activity of natural enzyme can be retained, its stability can be improved again, all improve a lot in heat-resisting, acid and alkali-resistance and antipepsin decomposition etc. simultaneously.Chinese patent CN101323845A and CN103805588A individually discloses the preparation method of modified by lauroyl chloride superoxide dismutase and the preparation method of lauric acid modification superoxide dismutase, and how further raising Product Activity and yield are the problems needing to solve.
Summary of the invention
For above-mentioned the deficiencies in the prior art, the object of this invention is to provide a kind of preparation method of La-SOD to improve activity and the yield of La-SOD.
Technical solution of the present invention is: a kind of preparation method of La-SOD, to comprise with lauric acid and sulfur oxychloride for raw material, obtains lauroyl chloride with pyridine DMF for catalyzer carries out catalyzed reaction, under the alkaline condition of 40 ~ 48 DEG C, carry out acylation reaction with lauroyl chloride and superoxide-dismutase, to getting the thermograde process of supernatant liquor I by 3 ~ 6 grades after the filtration of acylation reaction thing, the thermograde process of described 3 ~ 6 grades is initial temperature is 40 ~ 45 DEG C, every grade of temperature difference is 5 ~ 10 DEG C, the low temperature of final stage process is 5 ~ 10 DEG C, wherein the process of chopped-off head thermograde supernatant liquor I is cooled to rapidly initial temperature by initial temperature deduct the low temperature after every grade of temperature difference, and keep rapid temperature increases to initial temperature after 10 ~ 15 minutes carry out 3500 ~ 4500 revs/min centrifugal 10 ~ 30 minutes, removing precipitation gets supernatant liquor, follow-up every grade of thermograde process is that after previous stage supernatant liquor is cooled to rapidly previous stage process by temperature after previous stage process, temperature deducts the low temperature after every grade of temperature difference, and keep rapid temperature increases after 10 ~ 15 minutes to the low temperature of previous stage process carry out 3500 ~ 4500 revs/min centrifugal 10 ~ 30 minutes, removing precipitation gets supernatant liquor, 2 grades of precipitation sterilizing purification processes are carried out to the supernatant liquor II after final stage process and obtains La-SOD.
Described 2 grades of precipitation sterilizing purification processes be to supernatant liquor II add 1 ~ 5 times of volume lower than the dehydrated alcohol of-10 DEG C, abundant stirring, 3500 ~ 4500 revs/min centrifugal 5 ~ 15 minutes, abandon supernatant liquor, precipitation is dissolved in the sterilized water of 2 ~ 5 times of volumes, after abundant dissolving, repeat aforesaid operations, leave and take precipitation.
Described catalyzed reaction comprises the steps: to be that the lauric acid of 100ml ︰ 6 ~ 7g and sulfur oxychloride to join in reactor and to add catalyst pyridine DMF by lauric acid ︰ pyridine DMF volume ratio 100 ︰ 4 ~ 5 by moon osmanthus acid ︰ sulfur oxychloride envelope-bulk to weight ratio, be heated to 90 ~ 93 DEG C, stirring reaction 1 ~ 2 hour, reflux 1 ~ 2 hour, backflow terminates, and allows reactant carry out fractionation again, decompression, remove excessive sulfur oxychloride, collect the cut of 146 ~ 150 DEG C, obtain lauroyl chloride.
It is in 8.0 ~ 9.2 potassium phosphate buffers that described acylation reaction comprises the steps: that superoxide-dismutase is dissolved in pH according to weightmeasurement ratio 1g ︰ 50 ~ 500ml, slow dropping lauroyl chloride, superoxide-dismutase solution and lauroyl chloride mol ratio are 1 ︰ 80 ~ 3000; After abundant stirring, drip the sodium hydroxide solution of 0.5mol/L, regulate the pH value of superoxide-dismutase solution to be that 8.0 ~ 9.2, pH is stable in 30 minutes and be not only changed to; Above-mentioned solution is positioned over the stirred in water bath 1 ~ 1.5 hour of 40 ~ 48 DEG C.
The pH value of described superoxide-dismutase solution is 8.8.
The present invention beneficial effect be the activity of the superoxide-dismutase that the lauric acid obtained by the method is modified and yield all comparatively prior art be improved; The superoxide-dismutase that lauric acid is modified is compared superoxide-dismutase and is all improved a lot in heat-resisting, acid and alkali-resistance and antipepsin decomposition etc.The present invention has that technique is simple, the cycle is short, earning rate is high, has higher economic results in society.
Embodiment
Below in conjunction with embodiment, the invention will be further described, but not as a limitation of the invention.
Embodiment 1
The catalyst pyridine DMF of 250ml lauric acid, 17g sulfur oxychloride and 12ml is joined in reactor, be heated to 93 DEG C, stirring reaction 2 hours, reflux again 2 hours, backflow terminates, and allows reactant carry out fractionation, decompression, remove excessive sulfur oxychloride, the cut collecting 146 ~ 150 DEG C obtains lauroyl chloride; Take superoxide-dismutase 50g to be dissolved in the pH8.5 sodium phosphate buffer of 5000ml, fully dissolve; In enzyme solution, slowly drip lauroyl chloride 200ml, after abundant stirring reaction, drip the sodium hydroxide solution of 0.5mol/L, the pH value maintaining enzyme solution is 8.8, until the pH of enzyme solution maintains, 8.8, pH is stable in 30 minutes not only to be changed to, and stops dripping sodium hydroxide.
Above-mentioned solution is positioned over the stirred in water bath 60 minutes of 40 DEG C, acidylates sufficient reacting and carry out; Suction filtration removing precipitation, gets supernatant liquor I.
Thermograde process: 3 grades of thermograde process are carried out to supernatant liquor I, elementary temperature is 40 DEG C, ultimate temperature is 10 DEG C, each interstage temperature gradient difference is 10 DEG C, supernatant liquor I is down to rapidly 30 DEG C by 40 DEG C, keep rising to rapidly 40 DEG C again after 10 minutes, 4000 revs/min centrifugal 20 minutes, removing precipitation, be cooled to rapidly 20 DEG C again, keep rising to rapidly 30 DEG C again after 10 minutes, 4000 revs/min centrifugal 20 minutes, removing precipitation, be cooled to rapidly 10 DEG C again, keep rising to rapidly 20 DEG C again after 10 minutes, 4000 revs/min centrifugal 20 minutes, removing precipitation, obtain supernatant liquor II.
The sterilizing of secondary alcohol settling is carried out to supernatant liquor II: the dehydrated alcohol adding-12 DEG C of 3 times of volumes, abundant stirring, namely white precipitate is produced, 4000 revs/min centrifugal 5 minutes, abandon supernatant liquor, precipitation is dissolved in the sterilized water of 4 times of volumes, after fully dissolving, repeat aforesaid operations, leave and take and precipitate about about 40g.
With the sodium phosphate buffer dissolution precipitation of the 50mmol/LpH=6.2 of 250ml, obtain the superoxide-dismutase solution that lauric acid is modified, obtain lyophilized powder after freeze-drying and be about 30g.
Embodiment 2
The catalyst pyridine DMF of 100ml lauric acid, 6g sulfur oxychloride and 4ml is joined in reactor, be heated to 90 DEG C, stirring reaction 1 hour, reflux 1 hour, backflow terminates, and allows reactant carry out fractionation again, decompression, remove excessive sulfur oxychloride, collect the cut of 146 ~ 150 DEG C, obtain lauroyl chloride; Take superoxide-dismutase 50g to be dissolved in the pH8.7 sodium phosphate buffer of 8000ml, fully dissolve; In enzyme solution, slowly drip lauroyl chloride 50ml, slowly drip, after abundant stirring reaction, drip the sodium hydroxide solution of 0.5mol/L, the pH value maintaining enzyme solution is 9.0, until the pH of enzyme solution maintains 9.0, pH is stable in 30 minutes not only to be changed to, and stops dripping sodium hydroxide.
Above-mentioned solution is positioned over the stirred in water bath 80 minutes of 45 DEG C, acidylates sufficient reacting and carry out; Cross and filter precipitation, get supernatant liquor I.
Thermograde process: 5 grades of thermograde process are carried out to supernatant liquor I, elementary temperature is 45 DEG C, ultimate temperature is 5 DEG C, each interstage temperature gradient difference is 8 DEG C, supernatant liquor I is down to rapidly 37 DEG C by 45 DEG C, keep rising to rapidly 45 DEG C again after 15 minutes, 3500 revs/min centrifugal 30 minutes, removing precipitation, be cooled to rapidly 29 DEG C again, keep rising to rapidly 37 DEG C again after 15 minutes, 3500 revs/min centrifugal 30 minutes, removing precipitation, be cooled to rapidly 21 DEG C again, keep rising to rapidly 29 DEG C again after 15 minutes, 3500 revs/min centrifugal 30 minutes, removing precipitation, be cooled to rapidly 13 DEG C again, keep rising to rapidly 21 DEG C again after 15 minutes, 3500 revs/min centrifugal 30 minutes, removing precipitation, be cooled to rapidly 5 DEG C again, keep rising to rapidly 13 DEG C again after 15 minutes, 3500 revs/min centrifugal 30 minutes, removing precipitation, obtain supernatant liquor II.
The sterilizing of secondary alcohol settling is carried out to supernatant liquor II :-10 DEG C of dehydrated alcohols adding 5 times of volumes, abundant stirring, produce white precipitate, centrifugal 5 minutes of low speed 4500 revs/min, abandon supernatant liquor, precipitation is dissolved in the sterilized water of 5 times of volumes, after fully dissolving, repeat aforesaid operations, leave and take and precipitate about about 50g.
With the sodium phosphate buffer dissolution precipitation of the 50mmol/LpH=6.3 of 350ml, obtain the superoxide-dismutase solution that lauric acid is modified, obtain lyophilized powder after freeze-drying and be about 40g.
Embodiment 3
The catalyst pyridine DMF of 200ml lauric acid, 13g sulfur oxychloride and 10ml is joined in reactor, be heated to 91 DEG C, stirring reaction 2 hours, reflux 2 hours, backflow terminates, and allows reactant carry out fractionation again, decompression, remove excessive sulfur oxychloride, collect the cut of 146 ~ 150 DEG C, obtain lauroyl chloride; Take superoxide-dismutase 40g to be dissolved in the pH8.0 sodium phosphate buffer of 2000ml, fully dissolve; In enzyme solution, slowly drip lauroyl chloride 120ml, slowly drip, after abundant stirring reaction, drip the sodium hydroxide solution of 0.5mol/L, the pH value maintaining enzyme solution is 9.2, until the pH of enzyme solution maintains 9.2, pH is stable in 30 minutes not only to be changed to, and stops dripping sodium hydroxide.
Above-mentioned solution is positioned over the stirred in water bath 90 minutes of 45 DEG C, acidylates sufficient reacting and carry out; Cross and filter precipitation, get supernatant liquor I.
Thermograde process: 6 grades of thermograde process are carried out to supernatant liquor I, elementary temperature is 40 DEG C, ultimate temperature is 10 DEG C, each interstage temperature gradient difference is 5 DEG C, supernatant liquor I is down to rapidly 35 DEG C by 40 DEG C, keep rising to rapidly 40 DEG C again after 15 minutes, 4500 revs/min centrifugal 10 minutes, removing precipitation, be cooled to rapidly 30 DEG C again, keep rising to rapidly 35 DEG C again after 15 minutes, 4500 revs/min centrifugal 10 minutes, removing precipitation, be cooled to rapidly 25 DEG C again, keep rising to rapidly 30 DEG C again after 15 minutes, 4500 revs/min centrifugal 10 minutes, removing precipitation, be cooled to rapidly 20 DEG C again, keep rising to rapidly 25 DEG C again after 15 minutes, 4500 revs/min centrifugal 10 minutes, removing precipitation, be cooled to rapidly 15 DEG C again, keep rising to rapidly 20 DEG C again after 15 minutes, 4500 revs/min centrifugal 10 minutes, removing precipitation, be cooled to rapidly 10 DEG C again, keep rising to rapidly 15 DEG C again after 15 minutes, 4500 revs/min centrifugal 10 minutes, removing precipitation, obtain supernatant liquor II.
The sterilizing of secondary alcohol settling is carried out to supernatant liquor II :-15 DEG C of dehydrated alcohols adding 4 times of volumes, abundant stirring, produce white precipitate, 3500 revs/min centrifugal 10 minutes, abandon supernatant liquor, precipitation is dissolved in the sterilized water of 4 times of volumes, after fully dissolving, repeat aforesaid operations, leave and take and precipitate about about 38g.
With the sodium phosphate buffer dissolution precipitation of the 50mmol/LpH=6.5 of 300ml, obtain the superoxide-dismutase solution that lauric acid is modified, obtain lyophilized powder after freeze-drying and be about 28g.
Embodiment 4
The catalyst pyridine DMF of 200ml lauric acid, 13g sulfur oxychloride and 10ml is joined in reactor, be heated to 91 DEG C, stirring reaction 2 hours, reflux 2 hours, backflow terminates, and allows reactant carry out fractionation again, decompression, remove excessive sulfur oxychloride, collect the cut of 146 ~ 150 DEG C, obtain lauroyl chloride; Take SOD-3 0g to be dissolved in the pH9.2 sodium phosphate buffer of 15000ml, fully dissolve; In enzyme solution, slowly drip lauroyl chloride 120ml, slowly drip, after abundant stirring reaction, drip the sodium hydroxide solution of 0.5mol/L, the pH value maintaining enzyme solution is 9.2, until the pH of enzyme solution maintains 9.2, pH is stable in 30 minutes not only to be changed to, and stops dripping sodium hydroxide.
Above-mentioned solution is positioned over the stirred in water bath 70 minutes of 48 DEG C, acidylates sufficient reacting and carry out; Cross and filter precipitation, get supernatant liquor I.
Thermograde process: 3 grades of thermograde process are carried out to supernatant liquor I, elementary temperature is 40 DEG C, ultimate temperature is 10 DEG C, each interstage temperature gradient difference is 10 DEG C, supernatant liquor I is down to rapidly 30 DEG C by 40 DEG C, keep rising to rapidly 40 DEG C again after 10 minutes, 4500 revs/min centrifugal 15 minutes, removing precipitation, be cooled to rapidly 20 DEG C again, keep rising to rapidly 30 DEG C again after 10 minutes, 4500 revs/min centrifugal 15 minutes, removing precipitation, be cooled to rapidly 10 DEG C again, keep rising to rapidly 20 DEG C again after 10 minutes, 4500 revs/min centrifugal 15 minutes, removing precipitation, obtain supernatant liquor II.
The sterilizing of secondary alcohol settling is carried out to supernatant liquor II :-10 DEG C of dehydrated alcohols adding 2 times of volumes, abundant stirring, produce white precipitate, 4500 revs/min centrifugal 10 minutes, abandon supernatant liquor, precipitation is dissolved in the sterilized water of 5 times of volumes, after fully dissolving, repeat aforesaid operations, leave and take and precipitate about about 36g.
With the sodium phosphate buffer dissolution precipitation of the 50mmol/LpH=6.5 of 320ml, obtain the superoxide-dismutase solution that lauric acid is modified, obtain lyophilized powder after freeze-drying and be about 28g.
Carry out analysis to each embodiment result to measure, specifically comprise determination of activity: determination of activity adopts assay NBT photoreduction, the mensuration of protein content adopts: Coomassie Brilliant Blue (Bradford method); Remaining determined amino acid: adopt TNBS volumetry; Molecular weight and purity testing: gel strength 12.5%, electrode buffer is for containing 0.1%SDS, Tris-glycine buffer, and coomassie brilliant blue R250 dyes.Measurement result is as shown in the table
Claims (5)
1. a preparation method for La-SOD, is characterized in that: comprise the following steps, and with lauric acid and sulfur oxychloride for raw material, obtains lauroyl chloride with pyridine DMF for catalyzer carries out catalyzed reaction, under the alkaline condition of 40 ~ 48 DEG C, carry out acylation reaction with lauroyl chloride and superoxide-dismutase, to getting the thermograde process of supernatant liquor I by 3 ~ 6 grades after the filtration of acylation reaction thing, the thermograde process of described 3 ~ 6 grades is initial temperature is 40 ~ 45 DEG C, every grade of temperature difference is 5 ~ 10 DEG C, the low temperature of final stage process is 5 ~ 10 DEG C, wherein the process of chopped-off head thermograde supernatant liquor I is cooled to rapidly initial temperature by initial temperature deduct the low temperature after every grade of temperature difference, and keep rapid temperature increases to initial temperature after 10 ~ 15 minutes carry out 3500 ~ 4500 revs/min centrifugal 10 ~ 30 minutes, removing precipitation gets supernatant liquor, follow-up every grade of thermograde process is that after previous stage supernatant liquor is cooled to rapidly previous stage process by temperature after previous stage process, temperature deducts the low temperature after every grade of temperature difference, and keep rapid temperature increases after 10 ~ 15 minutes to the low temperature of previous stage process carry out 3500 ~ 4500 revs/min centrifugal 10 ~ 30 minutes, removing precipitation gets supernatant liquor, 2 grades of precipitation sterilizing purification processes are carried out to the supernatant liquor II after final stage process and obtains La-SOD.
2. the preparation method of La-SOD according to claim 1, it is characterized in that: described 2 grades of precipitation sterilizing purification processes be to supernatant liquor II add 1 ~ 5 times of volume lower than the dehydrated alcohol of-10 DEG C, abundant stirring, 3500 ~ 4500 revs/min centrifugal 5 ~ 15 minutes, abandon supernatant liquor, precipitation is dissolved in the sterilized water of 2 ~ 5 times of volumes, after fully dissolving, repeat aforesaid operations, leave and take precipitation.
3. the preparation method of La-SOD according to claim 1 and 2, it is characterized in that: described catalyzed reaction comprises the steps: to be that the lauric acid of 100ml ︰ 6 ~ 7g and sulfur oxychloride to join in reactor and to add catalyst pyridine DMF by lauric acid ︰ pyridine DMF volume ratio 100 ︰ 4 ~ 5 by moon osmanthus acid ︰ sulfur oxychloride envelope-bulk to weight ratio, be heated to 90 ~ 93 DEG C, stirring reaction 1 ~ 2 hour, reflux again 1 ~ 2 hour, backflow terminates, reactant is allowed to carry out fractionation, decompression, remove excessive sulfur oxychloride, collect the cut of 146 ~ 150 DEG C, obtain lauroyl chloride.
4. the preparation method of La-SOD according to claim 1 and 2, it is characterized in that: it is in 8.0 ~ 9.2 potassium phosphate buffers that described acylation reaction comprises the steps: that superoxide-dismutase is dissolved in pH according to weightmeasurement ratio 1g ︰ 50 ~ 500ml, slow dropping lauroyl chloride, superoxide-dismutase solution and lauroyl chloride mol ratio are 1 ︰ 80 ~ 3000; After abundant stirring, drip the sodium hydroxide solution of 0.5mol/L, regulate the pH value of superoxide-dismutase solution to be that 8.0 ~ 9.2, pH is stable in 30 minutes and be not only changed to; Above-mentioned solution is positioned over the stirred in water bath 1 ~ 1.5 hour of 40 ~ 48 DEG C.
5. the preparation method of La-SOD according to claim 4, is characterized in that: the pH value of described superoxide-dismutase solution is 8.8.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111743795A (en) * | 2020-07-29 | 2020-10-09 | 苏州讯如电子科技有限公司 | Repair skin cream with blue light resisting function and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101323845A (en) * | 2007-06-14 | 2008-12-17 | 铁岭均坤生物工程有限公司 | Preparation of superoxide dismutase modified by lauroyl chloride |
| CN103805588A (en) * | 2013-02-28 | 2014-05-21 | 无锡华奇生物科技有限公司 | Method for modifying superoxide dismutase by using lauric acid |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101323845A (en) * | 2007-06-14 | 2008-12-17 | 铁岭均坤生物工程有限公司 | Preparation of superoxide dismutase modified by lauroyl chloride |
| CN103805588A (en) * | 2013-02-28 | 2014-05-21 | 无锡华奇生物科技有限公司 | Method for modifying superoxide dismutase by using lauric acid |
Non-Patent Citations (1)
| Title |
|---|
| GUI XINGFEN ET AL.: "Studies on the Preparation and the Stability of SOD Modified by Lauric Acid", 《WUHAN UNIVERSITY JOURNAL OF NATURAL SCIENCES》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111743795A (en) * | 2020-07-29 | 2020-10-09 | 苏州讯如电子科技有限公司 | Repair skin cream with blue light resisting function and preparation method thereof |
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