CN105198940A - Preparation technology of glucuronolactone - Google Patents
Preparation technology of glucuronolactone Download PDFInfo
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- CN105198940A CN105198940A CN201510679605.2A CN201510679605A CN105198940A CN 105198940 A CN105198940 A CN 105198940A CN 201510679605 A CN201510679605 A CN 201510679605A CN 105198940 A CN105198940 A CN 105198940A
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- glucuronic acid
- preparation technology
- acid lactone
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Abstract
The invention discloses a preparation technology of glucuronolactone, and belongs to the field of medicine raw material production. According to the preparation technology, acid pickling and water washing are mainly carried out on oxidized starch to remove impurities in the oxidized starch, the liquification and saccharification of the oxidized starch are faciliated, glycuronic acid, glucose, disaccharide and trisaccharide are obtained after the saccharification of the oxidized starch; by virtue of the property that glycuronic acid is easy to dissolve in ethyl alcohol (alcohol), but the glucose, disaccharide and trisaccharide are insoluble in alcohol, the glycuronic acid is subjected to separation and purification, so that the fermentation and impurity-removal technology is eliminated, and the production period is shortened by 72 h. The technology is simple in operation, short in reaction time, and low in requirements for equipment; the glucuronolactone prepared by the technology is high in yield and high in purity.
Description
Technical field
The invention belongs to medicine material production field, be specifically related to a kind of high purity Glucuronic acid lactone preparation technology.
Background technology
Glucuronic acid lactone is the good medicine for the treatment of hepatitis, liver cirrhosis and connective tissue disease, and China is the major country of production of Glucuronic acid lactone.Along with becoming increasingly conspicuous of environmental problem, the traditional method that nitric acid oxidation produces Glucuronic acid lactone is challenged.On the basis of Yuan Hua seminar of Central China University of Science and Technology technology abroad, adopt carried noble metal technology to produce Sumstar 190, though solve pollution problem when Sumstar 190 is produced, the hydrolysis of Sumstar 190 still adopts acid hydrolyzation to produce, and pollution still exists.Because Determination of Carboxyl Group Content in Oxidized Starches is low, be oxidized not thorough, therefore containing a large amount of impurity such as glucose, disaccharides, trisaccharide in hydrolyzed solution, cause difficulty, in order to solve this technical barrier to the crystallization of Glucuronic acid lactone after lactonizing, Yuan Hua seminar adopts three sub-band water technology, the moisture generated after as far as possible removing lactonization reaction, makes lactonization reaction more thorough, but the result done like this, make composition in system more complicated, the more difficult crystallization of Glucuronic acid lactone.As everyone knows, the honey of making due to metal ion in sugar industry acts on, and makes the sugar in mother liquor (molasses) be difficult to crystallization, equally because system is complicated, and Glucuronic acid lactone crystallization difficulty.Li Xiang seminar of Shaanxi Tech Univ is on the basis analyzing traditional Glucuronic acid lactone production technique, Fenton reagent Sumstar 190, Sumstar 190 enzymolysis, alcohol impurity-removing, stirring at normal temperature crystallization technique is adopted to obtain Glucuronic acid lactone, avoid a large amount of uses (this technology also handy acid certainly, alkali regulate the pH value of reaction system) of acid in oxidation, hydrolytic process, solve the pollution problem that Glucuronic acid lactone is produced.Can Glucuronic acid lactone be obtained according to ZL200810151100.9. (clean production method of glucuronolactone), ZL200910023005.5. (D-Glucose aldehydic acid-gamma lactone crystallization method) and 2014101006471 (Glucuronic acid lactone normal temperature crystallization method), but there is crystallization difficulty, product yield is low, purity does not reach requirement technical problem.
Summary of the invention
In order to overcome the defect that above-mentioned prior art exists, the object of the present invention is to provide a kind of Glucuronic acid lactone purifying process, this technological operation is simple, and the reaction times is short, low for equipment requirements, the Glucuronic acid lactone yield obtained through this technique is high, purity is high.
The present invention is achieved through the following technical solutions:
A kind of Glucuronic acid lactone preparation technology, comprises the following steps:
1) in yam starch, add deionized water, after stirring, regulation system pH value is 9.5, adds H while stirring
2o
2and FeSO
4, regulation system pH value is after 10, and reaction 2 ~ 5h, filters, and collects filter cake, by filter cake with after salt acid soak 3 ~ 5h, filters, with deionized water repetitive scrubbing filter cake until water lotion is in neutral, and not containing Cl
-, then drying process, obtained Sumstar 190;
2) in Sumstar 190, deionized water is added while stirring, obtained Sumstar 190 emulsion, regulation system pH value is 6.5, add α-amylase to be hydrolyzed reaction, then regulation system pH value is 4.5, adds saccharifying enzyme and carries out saccharification react, then filter, collect filtrate, be concentrated into no longer water outlet, obtained enriched material A;
3) by enriched material A in water-bath, add the alcohol (volume fraction) of 95% of enriched material A volume 1.5 ~ 3.5 times while stirring, filter after reaction 20 ~ 30min, collect filtrate, concentration and recovery alcohol, obtained enriched material B;
4) in enriched material B, add Glacial acetic acid/acetic anhydride, at 45 ~ 50 DEG C, react 3 ~ 5h, obtain mixed solution, mixed solution is concentrated, obtained concentrated solution C;
5) by concentrated solution C at 25 ~ 30 DEG C, be stirred to grain formation with 30 revs/min of constant speed, then be stirred to crystal with 50 revs/min of constant speed and occur in a large number, after leaving standstill process 3 ~ 5h, vacuum filtration, obtains crude product, by crude product washing, dry rear obtained Glucuronic acid lactone.
Step 1) be amount ratio by 1g:2 ~ 3mL, in yam starch, add deionized water while stirring.
Step 1) in the H that adds
2o
2be 1:5 ~ 6 with the volume ratio of deionized water; The FeSO added
4be 1:60 ~ 65 with the mass ratio of yam starch.
Step 1) in be the salt acid soak filter cake of employing 1 ~ 2mol/mL.
Step 2) be amount ratio by 1g:2 ~ 3mL, in Sumstar 190, add deionized water while stirring.
Step 2) add α-amylase, at 80 ~ 85 DEG C, be hydrolyzed 1 ~ 2h; And every 6 ~ 6.5g Sumstar 190 adds the α-amylase of 1mL.
Step 2) add saccharifying enzyme, saccharification process 12 ~ 15h at 50 ~ 55 DEG C; And every 35 ~ 40g Sumstar 190 adds the saccharifying enzyme of 1mL.
Step 2), 3), 4) described in concentrated be 0.085 ~ 0.009MPa in vacuum tightness, temperature is carry out under the condition of 50 ~ 55 DEG C.
Step 4) in the volume ratio of Glacial acetic acid and acetic anhydride be 2:1, volume ratio=(0.8 ~ 1) of enriched material B and Glacial acetic acid: 1.
Step 5) be use absolute ethanol washing crude product, then at 50 ~ 55 DEG C, be dried to constant weight and obtain Glucuronic acid lactone.
Compared with prior art, the present invention has following useful technique effect:
Glucuronic acid lactone preparation technology disclosed by the invention, adopts the relatively simple method of one, improves purity and the productive rate of Glucuronic acid lactone.Its main advantage is embodied in following two aspects:
The first, yam starch is at Fenton reagent (H
2o
2and FeSO
4) generate Sumstar 190 under effect, wherein containing the Fenton reagent that unreacted is complete, as Fe
2+/ Fe
3+, H
2o
2, Na
+deng, because starch is oxidized in the basic conditions, therefore wherein Fe
2+/ Fe
3+with Fe (OH)
2/ Fe (OH)
3form exist, Fe (OH)
2/ Fe (OH)
3easily be adsorbed on Sumstar 190, washing is difficult to be removed, in enzymolysis process, because system pH reduces, and Fe (OH)
2/ Fe (OH)
3become Fe again
2+/ Fe
3+, the activity of excessive metal ion inhibitory enzyme, makes enzyme digestion reaction be difficult to carry out completely, the carrying out of the yield of affecting glucose aldehydic acid and removal of impurities (wineization reaction).Therefore, the present invention adopts the process of acidleach, washing, Fenton reagent in Sumstar 190 can be removed completely, relieves the impact of metal ion on next step liquefaction, saccharification react.Pickling liquor can repeatedly use, and does not cause environment/pollutes less.Color and luster after Sumstar 190 washes with water is light yellow, and adopts the Sumstar 190 after acidleach of the present invention, washing to be snowy white.
The second, Sumstar 190 obtains glucuronic acid, glucose and a small amount of disaccharides, trisaccharide after liquefaction, saccharification, and because glucuronic acid is soluble in alcohol, and glucose, disaccharides, trisaccharide are insoluble to alcohol, utilize alcohol to be removed.The inventive method owing to eliminating the impurity such as glucose, disaccharides, trisaccharide in fermented liquid, thus is beneficial to the carrying out of lactonization reaction and the crystallization of Glucuronic acid lactone.Above two processing modes combine by the present invention, eliminate inhibitor and the impurity of reaction very easily, improve yield and the purity of Glucuronic acid lactone.Eliminate ion-exchange/membrane filtration etc. and remove deimpurity equipment investment, reduce the production cost of Glucuronic acid lactone.Meanwhile, zymamsis impurity removal process can be saved, more than 3 days production cycle can be shortened.The yield of Glucuronic acid lactone can be made to reach 14.3% through preparation technology of the present invention, purity reaches 99.8%.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail, and the explanation of the invention is not limited.
Embodiment 1
1) preparation of Sumstar 190
The deionized water of 300mL is added in there-necked flask, adds the yam starch of 150g while stirring, be 10 by the NaOH regulation system pH value of 2mol/L, add the H of 45mL while stirring
2o
2, 2.4g FeSO
4be react 4h, filtered while hot under the condition of 10 in pH value, filter cake (Sumstar 190) is placed in beaker, the HCl adding 2mol/L soaks 3h, agitation and filtration, is placed in beaker by filter cake, adds the deionized water of 300mL while stirring, agitation and filtration, in the same way, spend deionized water rinse filter cake until filtrate is neutral, and not containing Cl
-, dry Sumstar 190;
2) enzymolysis
According to the ratio adding 150mL deionized water in 75g Sumstar 190, in Sumstar 190, add deionized water while stirring obtain Sumstar 190 emulsion, adjust ph is 6.5, adds the α-amylase of 12mL, 1h is hydrolyzed at 85 DEG C, adjust ph is 4.5, adds 2mL saccharifying enzyme, saccharification 12h at 55 DEG C, filtered while hot, collect filtrate, be concentrated into be 0.085MPa/ temperature be 50 DEG C in vacuum tightness and no longer include till moisture slips out, obtain enriched material A;
3) purifying
Enriched material A is proceeded in there-necked flask, the alcohol of enriched material volume 1.5 times of 95v/v is added while stirring in the water-bath of 50 DEG C, stir 30min, supernatant liquor is poured out, under agitation, add the 95v/v alcohol of same volume again, after reaction 30min, separation of supernatant, merges supernatant liquor, be concentrated into be 0.009MPa/ temperature be 50 DEG C in vacuum tightness till no longer including and slipping and distribute, obtain enriched material B;
4) lactonization reaction
Glacial acetic acid/acetic anhydride is added in enriched material B, wherein the volume ratio of Glacial acetic acid and acetic anhydride is 2:1, volume ratio=the 1:1 of enriched material B and Glacial acetic acid, then reacts 4h and obtains mixed solution at 45 DEG C, by mixed solution temperature be 45 DEG C, vacuum tightness be 0.009Mpa under vacuum concentration obtain concentrated solution C;
5) crystallization
Concentrated solution C is proceeded in there-necked flask, at 28 DEG C, adopt stainless steel paddle, be that 30 revs/min of lower constant speed stir 12h and namely have grain formation at rotating speed, solution muddiness (this process is crystal formation), under 50 revs/min, continue constant speed again stir concentrated solution B50h, crystal occurs in a large number, and (this process is growing the grain, i.e. crystal growth phase), then 4h is left standstill, leave standstill final vacuum suction filtration, obtain crude product, use absolute ethanol washing crude product, then at 55 DEG C, be dried to constant weight and obtain Glucuronic acid lactone, purity through high-performance liquid chromatogram determination Glucuronic acid lactone is 99.2%.
Embodiment 2
1) preparation of Sumstar 190
The deionized water of 300mL is added in there-necked flask, adds the yam starch of 150g while stirring, be 9.5 by the NaOH regulation system pH value of 2mol/L, add the H of 43mL while stirring
2o
2, 2.3g FeSO
4be react 4h, filtered while hot under the condition of 10 in pH value, filter cake (Sumstar 190) is placed in beaker, the HCl adding 1.5mol/L soaks 3.5h, agitation and filtration, is placed in beaker by filter cake, adds the deionized water of 300mL while stirring, agitation and filtration, in the same way, spend deionized water rinse filter cake until filtrate is neutral, and not containing Cl
-, dry Sumstar 190.
2) enzymolysis
According to the ratio adding 150mL deionized water in 75g Sumstar 190, in Sumstar 190, add deionized water while stirring obtain Sumstar 190 emulsion, adjust ph is 6.5, adds the α-amylase of 10mL, 0.5h is hydrolyzed at 85 DEG C, adjust ph is 4.5, adds 2.5mL saccharifying enzyme, saccharification 24h at 55 DEG C, filtered while hot, collect filtrate, be concentrated into be 0.009MPa/ temperature be 45 DEG C in vacuum tightness and no longer include till moisture slips out, obtain enriched material A;
3) purifying
Enriched material A is proceeded in there-necked flask, the alcohol of enriched material volume 1.5 times of 95v/v is added while stirring in the water-bath of 50 DEG C, stir 30min, supernatant liquor is poured out, under agitation, add the 95v/v alcohol of enriched material volume 2.0 times of volumes again, after reaction 25min, separation of supernatant, merges supernatant liquor, be concentrated into be 0.085MPa/ temperature be 50 DEG C in vacuum tightness till no longer including and slipping and distribute, obtain enriched material B;
4) lactonization reaction
Glacial acetic acid/acetic anhydride is added in enriched material B, wherein the volume ratio of Glacial acetic acid and acetic anhydride is 2:1, volume ratio=the 0.8:1 of enriched material B and Glacial acetic acid, then at 45 DEG C, react 5h and obtain mixed solution, by mixed solution temperature be 45 DEG C, vacuum tightness be 0.009Mpa under vacuum concentration obtain concentrated solution C;
5) crystallization
Concentrated solution C is proceeded in there-necked flask, at 28 DEG C, adopt stainless steel paddle, be that 30 revs/min of lower constant speed stir 12h and namely have grain formation at rotating speed, solution muddiness (this process is crystal formation), under 50 revs/min, continue constant speed again stir concentrated solution B50h, crystal occurs in a large number, and (this process is growing the grain, i.e. crystal growth phase), then 4h is left standstill, leave standstill final vacuum suction filtration, obtain crude product, use absolute ethanol washing crude product, then at 55 DEG C, be dried to constant weight and obtain Glucuronic acid lactone, purity through high-performance liquid chromatogram determination Glucuronic acid lactone is 99.8%.
In sum, the present invention mainly carries out acidleach to Sumstar 190, washing, with removing impurity wherein, be conducive to the liquefaction of Sumstar 190, saccharification, glucuronic acid is obtained after Sumstar 190 saccharification, glucose, disaccharides, trisaccharide, because glucuronic acid is soluble in ethanol (alcohol), and glucose, disaccharides, trisaccharide is insoluble to alcohol, therefore utilize this character separating-purifying glucuronic acid, eliminate the fermentation impurity removal process in patent ZL200910023005.5. (D-Glucose aldehydic acid-gamma lactone crystallization method) and 2014101006471 (Glucuronic acid lactone normal temperature crystallization method), production cycle shortens 72h.The productivity ratio patent ZL200810151100.9. of the Glucuronic acid lactone adopting this patent to obtain improves 1.2%, reach 14.3%, purity improves 5.8% than patent ZL200810151100.9., reach 99%, and do not need to adopt the technology such as ion-exchange/membrane filtration just can improve purity and the productive rate of product.
The present invention contrasts crystallization theory, analyze and find reason, test through how many times, finding that Sumstar 190 is hydrolyzed halfway reason is that the purity of Sumstar 190 is low, containing the Fenton reagent that unreacted is complete in Sumstar 190, Fenton reagent suppresses the activity of amylase, saccharifying enzyme, make liquefaction, saccharification react is not thorough, saccharification product complicated component, also be unfavorable for the carrying out that wineization is reacted, the suitableeest substrate of wineization reaction is glucose, but the carrying out that disaccharides, trisaccharide inhibit wineization to react, make the product composition after wine complicated, do not reach wine and eliminate assorted object.Based on above analysis, acidleach, washing are carried out to the Sumstar 190 after Fenton reagent oxidation, the Fenton reagent (ferrous ion/iron ion, hydrogen peroxide) in removing Sumstar 190 and other ion.
Experiment finds, glucuronic acid is soluble in alcohol, and glucose, other polysaccharide and metal ion insoluble (slightly soluble) are in alcohol, therefore concentration is carried out to saccharified liquid, removal of impurities is carried out again with alcohol, supernatant liquor (alcohol liquid) is concentrated, obtains the glucuronic acid that purity is higher, because the crystallization of purity height just becomes comparatively easy after lactonizing.Above technology avoids the employing of ion-exchange, membrane filtration technique, reaches the object of removal of impurities.
Advantage of the present invention is mainly reflected in:
1, employing acidleach, washing eliminate the Fe (OH) be adsorbed on Sumstar 190 molecule
2/ Fe (OH)
3, pickling liquor can repeatedly use, and does not cause environment/pollutes less.Color and luster after Sumstar 190 washes with water is light yellow, and adopts the Sumstar 190 after acidleach, washing to be snowy white.
2, in saccharified liquid due to containing glucuronic acid, glucose, disaccharides, trisaccharide, adopt the moisture in vacuum concentration removal saccharified liquid, add the alcohol of enriched material amount 2.5-3.5 times 95v/v while stirring, collect filtrate 1, the alcohol of same amount is added while stirring in filter residue, collect filtrate 2, merging filtrate 1,2, vacuum concentration obtains glucuronic acid, lactonize and obtain Glucuronic acid lactone, zymamsis impurity removal process is saved in this invention, can shorten more than 3 days production cycle, save production cost.
Claims (10)
1. a Glucuronic acid lactone preparation technology, is characterized in that, comprises the following steps:
1) in yam starch, add deionized water, after stirring, regulation system pH value is 9.5, adds H while stirring
2o
2and FeSO
4, regulation system pH value is after 10, and reaction 2 ~ 5h, filters, and collects filter cake, by filter cake with after salt acid soak 3 ~ 5h, filters, with deionized water repetitive scrubbing filter cake until water lotion is in neutral, and not containing Cl
-, then drying process, obtained Sumstar 190;
2) in Sumstar 190, deionized water is added while stirring, obtained Sumstar 190 emulsion, regulation system pH value is 6.5, add α-amylase to be hydrolyzed reaction, then regulation system pH value is 4.5, adds saccharifying enzyme and carries out saccharification react, then filter, collect filtrate, be concentrated into no longer water outlet, obtained enriched material A;
3) by enriched material A in water-bath, add the alcohol of 95% of enriched material A volume 1.5 ~ 3.5 times while stirring, filter after reaction 20 ~ 30min, collect filtrate, concentration and recovery alcohol, obtained enriched material B;
4) in enriched material B, add Glacial acetic acid/acetic anhydride, at 45 ~ 50 DEG C, react 3 ~ 5h, obtain mixed solution, mixed solution is concentrated, obtained concentrated solution C;
5) by concentrated solution C at 25 ~ 30 DEG C, be stirred to grain formation with 30 revs/min of constant speed, then be stirred to crystal with 50 revs/min of constant speed and occur in a large number, after leaving standstill process 3 ~ 5h, vacuum filtration, obtains crude product, by crude product washing, dry rear obtained Glucuronic acid lactone.
2. a kind of Glucuronic acid lactone preparation technology according to claim 1, is characterized in that, step 1) be by 1g:(2 ~ 3) amount ratio of mL, in yam starch, add deionized water while stirring.
3. a kind of Glucuronic acid lactone preparation technology according to claim 1, is characterized in that, step 1) in the H that adds
2o
2be 1:(5 ~ 6 with the volume ratio of deionized water); The FeSO added
4be 1:(60 ~ 65 with the mass ratio of yam starch).
4. a kind of Glucuronic acid lactone preparation technology according to claim 1, is characterized in that, step 1) in be the salt acid soak filter cake of employing 1 ~ 2mol/mL.
5. a kind of Glucuronic acid lactone preparation technology according to claim 1, is characterized in that, step 2) be by 1g:(2 ~ 3) amount ratio of mL, in Sumstar 190, add deionized water while stirring.
6. a kind of Glucuronic acid lactone preparation technology according to claim 1, is characterized in that, step 2) add α-amylase, at 80 ~ 85 DEG C, be hydrolyzed 1 ~ 2h; And every 6 ~ 6.5g Sumstar 190 adds the α-amylase of 1mL.
7. a kind of Glucuronic acid lactone preparation technology according to claim 1, is characterized in that, step 2) add saccharifying enzyme, saccharification process 12 ~ 15h at 50 ~ 55 DEG C; And every 35 ~ 40g Sumstar 190 adds the saccharifying enzyme of 1mL.
8. a kind of Glucuronic acid lactone preparation technology according to claim 1, is characterized in that, step 2), 3), 4) described in concentrated be 0.085 ~ 0.009MPa in vacuum tightness, temperature is carry out under the condition of 50 ~ 55 DEG C.
9. a kind of Glucuronic acid lactone preparation technology according to claim 1, is characterized in that, step 4) in the volume ratio of Glacial acetic acid and acetic anhydride be 2:1, volume ratio=(0.8 ~ 1) of enriched material B and Glacial acetic acid: 1.
10. a kind of Glucuronic acid lactone preparation technology according to claim 1, is characterized in that, step 5) be use absolute ethanol washing crude product, then at 50 ~ 55 DEG C, be dried to constant weight and obtain Glucuronic acid lactone.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108486187A (en) * | 2018-02-02 | 2018-09-04 | 南京微构医药科技有限公司 | A kind of preparation process of iduronic acid |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382198A (en) * | 1980-01-09 | 1983-05-03 | Tektronix, Inc. | Amplitude limiter circuit |
| CN101363036A (en) * | 2008-09-25 | 2009-02-11 | 陕西科技大学 | Clean production method of glucuronolactone |
| CN101575625A (en) * | 2009-06-19 | 2009-11-11 | 陕西科技大学 | Method for crystallizing D-glucuronic acid gamma-lactone |
| CN101792780A (en) * | 2010-01-13 | 2010-08-04 | 陕西科技大学 | Separation method of D-glucuronic acid gamma-lactone |
| CN103882077A (en) * | 2014-03-18 | 2014-06-25 | 陕西科技大学 | Normal temperature crystallization method of glucuronolactone |
| CN104119405A (en) * | 2014-07-04 | 2014-10-29 | 陕西科技大学 | Fast vacuum concentration method for glucurolactone |
-
2015
- 2015-10-19 CN CN201510679605.2A patent/CN105198940B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382198A (en) * | 1980-01-09 | 1983-05-03 | Tektronix, Inc. | Amplitude limiter circuit |
| CN101363036A (en) * | 2008-09-25 | 2009-02-11 | 陕西科技大学 | Clean production method of glucuronolactone |
| CN101575625A (en) * | 2009-06-19 | 2009-11-11 | 陕西科技大学 | Method for crystallizing D-glucuronic acid gamma-lactone |
| CN101792780A (en) * | 2010-01-13 | 2010-08-04 | 陕西科技大学 | Separation method of D-glucuronic acid gamma-lactone |
| CN103882077A (en) * | 2014-03-18 | 2014-06-25 | 陕西科技大学 | Normal temperature crystallization method of glucuronolactone |
| CN104119405A (en) * | 2014-07-04 | 2014-10-29 | 陕西科技大学 | Fast vacuum concentration method for glucurolactone |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108486187A (en) * | 2018-02-02 | 2018-09-04 | 南京微构医药科技有限公司 | A kind of preparation process of iduronic acid |
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