CN1865438A - Novel fixed enzyme vector comprising epoxy group and its preparation method and uses - Google Patents
Novel fixed enzyme vector comprising epoxy group and its preparation method and uses Download PDFInfo
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- CN1865438A CN1865438A CN 200510013522 CN200510013522A CN1865438A CN 1865438 A CN1865438 A CN 1865438A CN 200510013522 CN200510013522 CN 200510013522 CN 200510013522 A CN200510013522 A CN 200510013522A CN 1865438 A CN1865438 A CN 1865438A
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Abstract
The invention discloses a new typed immobilized enzyme carrier with epoxy radicals and preparing method and utility, which is composed of cross-linking polymer resin with epoxy radicals and hydrophilicity amido and hydroxyl group. The invention displays high hydrophilicity, mechanic strength and stable chemical property, which can carry all enzyme and other proteins.
Description
[technical field]
The present invention relates to enzyme immobilization carrier, specifically contain the crosslinking polymerization resin of epoxy group(ing) functional group and hydrophilic amide group and hydroxyl, as enzyme immobilization carrier.
[background technology]
Panoramic chemical reaction all carries out under enzyme catalysis in the organism.The characteristics of enzymic catalytic reaction have: 1. catalytic efficiency height, and transformation efficiency often can reach 100%; 2. the specificity height is very high to the catalytic selectivity of reactant (low thing), the product purity height, and side reaction is few; 3. the reaction conditions gentleness is reflected to reach under the normal pressure about organism body temperature temperature and carries out, and reaction medium is water (find also that in recent years some enzymic catalytic reactions can carry out in organic solvent, this has expanded the range of application of enzymic catalytic reaction widely).Therefore people attempt enzymic catalytic reaction is applied in the Industrial Catalysis, are used for synthetic some compound.But enzymic catalytic reaction also has shortcoming, mainly is: the enzyme price is higher, reclaims difficulty, and therefore synthetic cost is higher; The enzyme pollution products that is difficult for recovery increases the purifying expense of product; Enzyme to environment as sensitivities such as heat, acid, alkali, easy inactivation.The immobilization technology of enzyme has then partly solved enzymatic above-mentioned shortcoming, immobilized enzyme is easy to the enzyme recovery is used again, reusing number of times can reduce the cost of enzymic catalytic reaction widely up to thousands of times, and has solved the problem of residual enzyme pollution reaction product.The immobilization of enzyme increases the stability of heat-resisting, sour, the alkali of enzyme toward contact, makes the longer service life of enzyme.
The process for fixation of enzyme has: absorption method, ion exchange method, entrapping method, covalent linkage fixation method etc.Wherein make the enzyme molecule most widely used by the immobilized method on carrier of covalent linkage with amino or sulfydryl reaction by epoxy group(ing) on the carrier and enzyme molecule, because enzyme all contains amino as protein, the carrier that therefore contains epoxy group(ing) is the universality carrier of immobilized enzyme.The carrier of immobilized enzyme should have the following performance: active height, the good hydrophilic property of immobilized enzyme, chemical stability is good, physical strength is high, be that porousness and aperture are bigger etc. for the immobilization need carrier of the bigger enzyme of molecular weight.The epoxy group(ing) carrier that contains of bibliographical information comprises: (1) natural macromolecular material, and as Mierocrystalline cellulose, dextran, agarose etc., the advantage of examples of such carriers is a good hydrophilic property, shortcoming is bad mechanical strength, readily biodegradable, cost height.(2) synthetic macromolecule carrier, examples of such carriers comprises a variety of again.Study the cross-linked poly-methyl methacrylate glycidyl ester that maximum carriers obtains for the suspension polymerization by aqueous phase, the linking agent of use has divinylbenzene and methacrylate glycol ester.The advantage of this kind carrier be synthetic simple, cost is low, its shortcoming is that the wetting ability of skeleton is poor, and polymer fragment is fallen down on the surface of carrier gradually when stirring because of the rigidity of skeleton, not only easily makes the filter betting contest of aftertreatment, pollution products, and the work-ing life of immobilized enzyme is short.Germany Rohm company adopts the inverse suspension polymerization method, with Methacrylamide, N, N '-methene-two Methacrylamides, glycidyl methacrylate and propylene glycidyl ether are monomer, good, the physical strength advantages of higher of the carrier possess hydrophilic property that synthetic contains epoxy group(ing) is up to the present most popular enzyme immobilization carrier.This shortcoming is: because Methacrylamide and N, N '-methene-two Methacrylamides are water-soluble monomer, and glycidyl methacrylate and propylene glycidyl ether are fat-soluble monomer, the solubleness of the latter in water is very low, their allocation proportions in oil phase big than at aqueous phase when inverse suspension polymerization, this not only makes these two kinds of monomeric utilization ratios very low.And making the balling ratio of suspension polymerization very low in such distribution, the resin bead body easily is bonded to piece in the polymerization process, makes the yield of carrier very low.Another shortcoming is that inverse suspension polymerization is difficult to obtain macroporous resin.
[summary of the invention]
Purpose of the present invention is just at the shortcoming of above-mentioned existing enzyme immobilization carrier, propose a kind of employing contain hydrophilic amide group and hydroxyl and contain the gel-type of epoxy group(ing) functional group or the crosslinking polymerization resin of macroporous type as the carrier of enzyme immobilization, and prepare this resin and utilize this carrier method.
Novel fixed enzyme vector comprising epoxy group of the present invention is characterized in that containing the crosslinking polymerization resin of epoxy group(ing) functional group and hydrophilic amide group and hydroxyl, as the carrier of enzyme immobilization.The skeleton of carrier and functional group can be represented with following structural formula:
R=H or CH
3
The preparation method of novel fixed enzyme vector comprising epoxy group of the present invention is characterized in that:
A. methyl acrylate or methyl methacrylate and divinylbenzene carry out the suspension free-radical copolymerization, obtain gel-type polymethyl acrylate or plexiglass;
Or methyl acrylate or methyl methacrylate and divinylbenzene carry out the suspension free-radical copolymerization in the presence of pore-creating agent, obtains macroporous type polymethyl acrylate or plexiglass;
B. polymethyl acrylate or plexiglass and thanomin reaction obtains described resin with epichlorohydrin reaction then.
The purposes of novel fixed enzyme vector comprising epoxy group of the present invention is characterized in that described resin that contains epoxy group(ing) and enzyme in the medium of pH 6-14, and at 4 ℃ to room temperature reaction 2-48 hour that enzyme is immobilized on resin, making supported quantity is 10-150mg enzyme/g resin.
Carrier of the present invention have polymer backbone highly hydrophilic, both can make macroporous type and can make also that good, can the be immobilized all enzymes of gel-type, physical strength height, chemistry and biologically stable and other protein, synthesis technique are simple, the enzymic activity advantages of higher of immobilized enzyme.
[embodiment]
Novel fixed enzyme vector comprising epoxy group, it contains the crosslinking polymerization resin of epoxy group(ing) functional group and hydrophilic amide group and hydroxyl, both can be the resin of gel-type, also can be the resin of macroporous type.
The synthetic method of this carrier is: at first methyl acrylate or methyl methacrylate and divinylbenzene carry out suspending copolymerization and obtain gel-type polymethyl acrylate or plexiglass; Or methyl acrylate or methyl methacrylate and divinylbenzene carry out the suspension free-radical copolymerization in the presence of pore-creating agent, obtains macroporous type polymethyl acrylate or plexiglass.
The polymethyl acrylate of gel-type or macroporous type or plexiglass and thanomin carry out the aminolysis reaction of ester then, obtain containing the resin of the highly-hydrophilic of amide group and hydroxyl, resin behind the aminolysis and epichlorohydrin reaction obtain final enzyme immobilization carrier of the present invention.
In the resin behind aminolysis and the reaction of epoxy chloropropane, have only very the hydroxyl of small proportion that reaction has taken place on the resin and introduce functional group, all the other most of hydroxyls still keep, to guarantee the wetting ability of carrier.The building-up reactions formula can be expressed as follows:
R=H or CH
3
The degree of crosslinking that methyl acrylate or methyl methacrylate and divinylbenzene carry out suspending copolymerization is 2-20%, obtains gel-type polymethyl acrylate or plexiglass.In above-mentioned suspension copolymerization, add pore-creating agent, then obtain macroporous type polymethyl acrylate or plexiglass.Degree of crosslinking is 6-40%.The part by weight of monomer and pore-creating agent is 1: 0.3-1: 2.Pore-creating agent can be aromatic hydrocarbons such as toluene, higher alcohols such as butanols, hexanol, hexalin, alkanes such as heptane, industrial naptha, whiteruss, solid paraffin etc.Pore-creating agent can use separately or any two kinds mixing is used.
The temperature of reaction of the reaction of gel-type or macroporous type polymethyl acrylate or plexiglass and thanomin is 50-150 ℃, and the reaction times is 2-48 hour.
The aminolysis reaction gained resin of gel-type or macroporous type polymethyl acrylate or plexiglass and thanomin and the reaction of epoxy chloropropane both can be used acid catalysis, also can use base catalysis.
When using acid catalysis, available dioxane, tetrahydrofuran (THF) are as solvent, and the weight ratio of resin and acid catalyst (sulfuric acid) is 1: 0.01-1: 0.2, and the weight ratio of resin and epoxy chloropropane is 1: 0.1-1: 2, temperature of reaction is 50 ℃ and arrives reflux temperature that the reaction times is 8-24 hour.
When using base catalysis, the mixture as solvent of used water, dimethyl sulfoxide (DMSO) or water and dimethyl sulfoxide (DMSO), the ratio of water and dimethyl sulfoxide (DMSO) is 1: 0-0: 1, the weight ratio of resin and epoxy chloropropane is 1: 0.1-1: 2, and the mole number of alkali (sodium hydroxid or potassium hydroxide) is 1.1 times of epoxy chloropropane mole number.
Under the weakly alkaline condition, enzyme and the above-mentioned resin that contains epoxy group(ing) react under room temperature at 2 ℃ in neutrality, and enzyme passes through hydroxyl on it and/or sulfydryl and epoxy reaction and enzyme is immobilized on carrier.As protein; any enzyme all contains amido; and carrier of the present invention contains the active epoxy group(ing) that is easy to amido reaction, so examples of such carriers is fit to the fixing of any enzyme, for example penicillin acylase, glucase, glucose isomerase, cyan-hydrolysis enzyme, lipase, proteolytic enzyme etc.
Embodiment 1
The preparation of gel-type polymethylmethacrylate:
In the 1000ml there-necked flask, add the aqueous solution that 400ml contains 5% sodium-chlor and 0.5% polyvinyl alcohol, the organic phase solution that adding is made up of 92.6g methyl methacrylate, 7.4g divinylbenzene (content is 54.3%) and 0.5g benzoyl peroxide, adjust stirring velocity, the organic phase liquid pearl diameter that makes aqueous phase is warmed up to 80 ℃ and kept 8 hours under this stirring velocity between the 30-60 order.With the gained bead polymer with hot wash for several times, dry, 30-60 order resin is got in screening.
Embodiment 2
The preparation of gel-type polymethyl acrylate:
In the 1000ml there-necked flask, add the aqueous solution that 400ml contains 5% sodium-chlor and 0.5% polyvinyl alcohol, the organic phase solution that adding is made up of 89.0g methyl acrylate, 11.0g divinylbenzene (content is 54.3%) and 0.5g benzoyl peroxide, adjust stirring velocity, the organic phase liquid pearl diameter that makes aqueous phase is warmed up to 80 ℃ and kept 8 hours under this stirring velocity between the 30-60 order.With the gained bead polymer with hot wash for several times, dry, 30-60 order resin is got in screening.
Embodiment 3
The preparation of macroporous type polymethylmethacrylate:
In the 1000ml there-necked flask, add the aqueous solution that 400ml contains 5% sodium-chlor and 0.5% polyvinyl alcohol, the organic phase solution that adding is made up of 40.1g methyl methacrylate, 19.9g divinylbenzene (content is 54.3%), 48g propyl carbinol and 0.3g benzoyl peroxide, adjust stirring velocity, the organic phase liquid pearl diameter that makes aqueous phase is warmed up to 80 ℃ and kept 8 hours under this stirring velocity between the 30-60 order.With the gained bead polymer with hot wash for several times, dry the back and use acetone extraction 6 hours in apparatus,Soxhlet's, 30-60 order resin is got in screening.
Embodiment 4
The preparation of macroporous type polymethyl acrylate:
In the 1000ml there-necked flask, add the aqueous solution that 400ml contains 5% sodium-chlor and 0.5% polyvinyl alcohol, the organic phase solution that adding is made up of 27g methyl acrylate, 23g divinylbenzene (content is 54.3%), 33.3g toluene, 16.7g whiteruss and 0.25g benzoyl peroxide, adjust stirring velocity, the organic phase liquid pearl diameter that makes aqueous phase is warmed up to 80 ℃ and kept 8 hours under this stirring velocity between the 30-60 order.With the gained bead polymer with hot wash for several times, dry the back and use acetone extraction 8 hours in apparatus,Soxhlet's, 30-60 order resin is got in screening.
Embodiment 5
The aminolysis of embodiment 1 gained plexiglass:
30g embodiment 1 gained plexiglass is suspended in the 300ml thanomin, is heated to 120 ℃ of reactions 24 hours under stirring, and the gained resin washes neutrality with water, drying.The nitrogen content that records resin is 9.6%.
Embodiment 6-8
The aminolysis of embodiment 2-4 gained resin:
With used plexiglass among embodiment 2, embodiment 3 and embodiment 4 gained polymethyl acrylate resins or the plexiglass replacement embodiment 5, make identical operations respectively.The nitrogen content of gained resin is respectively: 10.5%, 6.5% and 6.0%.
Embodiment 9
The alkaline epoxy groupization of embodiment 5 gained aminolysis resins:
10g embodiment 5 gained aminolysis resins are suspended in the mixed solution of 70ml dimethyl sulfoxide (DMSO) and 30ml water, add the 10g epoxy chloropropane, under agitation dripping saturated sodium hydroxide solution makes the pH value of system between 10-12, react and wash resin with water to washings neutrality after 8 hours, must contain the resin of epoxy group(ing).Epoxy group content is 1.2mmol/g.
Embodiment 10
The acid epoxy groupization of embodiment 6 gained aminolysis resins:
10g embodiment 6 gained aminolysis resins are suspended in 70ml dioxane, 5g epoxy chloropropane and the 1g sulfuric acid, under agitation be heated to 115 ℃ of reactions 12 hours, wash resin with water to washings neutrality, then resin is suspended in the 50ml sodium hydroxide solution (0.5mol/L) and stirred 30 minutes, wash neutrality with water, must contain the resin of epoxy group(ing).Epoxy group content is 1.6mmol/g.
Embodiment 11
The alkaline epoxy groupization of embodiment 7 gained aminolysis resins:
10g embodiment 7 gained aminolysis resins are suspended in the mixed solution of 50ml dimethyl sulfoxide (DMSO) and 50ml water, add the 10g epoxy chloropropane, under agitation dripping saturated sodium hydroxide solution makes the pH value of system between 10-12, react and wash resin with water to washings neutrality after 8 hours, must contain the resin of epoxy group(ing).Epoxy group content is 1.4mmol/g.
Embodiment 12
The alkaline epoxy groupization of embodiment 8 gained aminolysis resins:
10g embodiment 8 gained aminolysis resins are suspended in the mixed solution of 50ml dimethyl sulfoxide (DMSO) and 50ml water, add the 10g epoxy chloropropane, under agitation dripping saturated sodium hydroxide solution makes the pH value of system between 10-12, react and wash resin with water to washings neutrality after 8 hours, must contain the resin of epoxy group(ing).Epoxy group content is 0.8mmol/g.
Embodiment 13
Embodiment 9 gained epoxy-containing yl resin immobilizing trypsinases:
1g embodiment 9 gained epoxy-containing yl resins are suspended in the trypsinase phosphoric acid buffer that the ice-cold concentration of 10ml is 4mg/ml (pH 7.0), and vibration is 48 hours under 4 ℃ of conditions, gets immobilizing trypsinase.The amount of immobilized protein is 24mg/g, and the activity of immobilizing trypsinase is 120U/g.
Embodiment 14
Embodiment 10 gained epoxy-containing yl resin immobilization rizolipases:
1g embodiment 10 gained epoxy-containing yl resins are suspended in (pH 7.5, and enzyme is lived and is 10U/ml) in the phosphoric acid buffer of 5ml rizolipase, and vibration is 12 hours under 25 ℃ of conditions, the immobilization rizolipase.The amount of immobilized protein is 30mg/g, and the activity of immobilization rizolipase is 32U/g.
Embodiment 15
Embodiment 11 gained epoxy-containing yl resin immobilized penicillin acylated enzymes:
1g embodiment 11 gained epoxy-containing yl resins are suspended in the phosphoric acid buffer of penicillin acylase that 10ml concentration is 8mg/ml (pH 7.5), and vibration is 24 hours under 25 ℃ of conditions, immobilized penicillin acylated enzyme.The amount of immobilized protein is 46mg/g, and the immobilized penicillin acylated enzyme activity is 482U/g.
Embodiment 16
Embodiment 12 gained epoxy-containing yl resin fixed glucose isomerases:
1g embodiment 12 gained epoxy-containing yl resins are suspended in the phosphoric acid buffer that 10ml concentration is the glucose isomerase of 10mg/ml (pH 7.5), and vibration is 24 hours under 25 ℃ of conditions, gets fixed glucose isomerase.The amount of immobilized protein is 46mg/g, and the activity of fixed glucose isomerase is 2350U/g.
Claims (10)
1. novel fixed enzyme vector comprising epoxy group is characterized in that it being the crosslinking polymerization resin that contains epoxy group(ing) functional group and hydrophilic amide group and hydroxyl by shown in the following structural formula, as the carrier of enzyme immobilization:
R=H or CH
3
2. according to the described carrier of claim 1, it is characterized in that said resin both can be the resin of gel-type, also can be the resin of macroporous type.
3. the preparation method of the novel fixed enzyme vector comprising epoxy group of claim 1 is characterized in that:
A. methyl acrylate or methyl methacrylate and divinylbenzene carry out the suspension free-radical copolymerization, obtain gel-type polymethyl acrylate or plexiglass;
Or methyl acrylate or methyl methacrylate and divinylbenzene carry out the suspension free-radical copolymerization in the presence of pore-creating agent, obtains macroporous type polymethyl acrylate or plexiglass;
B. polymethyl acrylate or plexiglass and thanomin reaction obtains described resin with epichlorohydrin reaction then.
4. in accordance with the method for claim 3, the degree of crosslinking that it is characterized in that gel-type polymethyl acrylate or plexiglass is 2-20%; The degree of crosslinking of macroporous type polymethyl acrylate or plexiglass is 6-40%.
5. in accordance with the method for claim 3, it is characterized in that macroporous type polymethyl acrylate or plexiglass, its pore-creating agent can be: aromatic hydrocarbons such as toluene, higher alcohols such as butanols, hexanol, hexalin, alkanes such as heptane, industrial naptha, whiteruss, solid paraffin etc., pore-creating agent can use separately or any two kinds mixing is used, and the part by weight of monomer and pore-creating agent is 1: 0.3-1: 2.
6. in accordance with the method for claim 3, it is characterized in that the temperature of reaction of gel-type or macroporous type polymethyl acrylate or plexiglass and thanomin reaction is 50-150 ℃, the reaction times is 2-48 hour.
7. in accordance with the method for claim 3, it is characterized in that the resin of gel-type or macroporous type polymethyl acrylate or plexiglass and thanomin reaction gained and the reaction of epoxy chloropropane, both can use acid catalysis, also can use base catalysis.
8. according to claim 3 and the described method of claim 7, when it is characterized in that using acid catalysis, available dioxane, tetrahydrofuran (THF) are as solvent, the weight ratio of resin and acid catalyst is 1: 0.01-1: 0.2, the weight ratio of resin and epoxy chloropropane is 1: 0.1-1: 2, temperature of reaction is 50 ℃ and arrives reflux temperature that the reaction times is 8-24 hour.
9. according to claim 3 and the described method of claim 7, when it is characterized in that using base catalysis, the mixture as solvent of used water, dimethyl sulfoxide (DMSO) or water and dimethyl sulfoxide (DMSO), the ratio of water and dimethyl sulfoxide (DMSO) is 1: 0-0: 1, the weight ratio of resin and epoxy chloropropane is 1: 0.1-1: 2, and the mole number of alkali is 1.1 times of epoxy chloropropane mole number.
10. the purposes of the novel fixed enzyme vector comprising epoxy group of claim 1, it is characterized in that described resin that contains epoxy group(ing) and enzyme are in the medium of pH6-14, at 4 ℃ to room temperature reaction 2-48 hour, enzyme is immobilized on resin, and making supported quantity is 10-150mg enzyme/g resin.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100135226A CN100564523C (en) | 2005-05-18 | 2005-05-18 | Contain epoxy group(ing) fixed enzyme vector and preparation method and purposes |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100135226A CN100564523C (en) | 2005-05-18 | 2005-05-18 | Contain epoxy group(ing) fixed enzyme vector and preparation method and purposes |
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| CN1865438A true CN1865438A (en) | 2006-11-22 |
| CN100564523C CN100564523C (en) | 2009-12-02 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101864410A (en) * | 2010-04-16 | 2010-10-20 | 华东理工大学 | Epoxy mesoporous molecular sieve for use in bio-enzyme immobilization and preparation method thereof |
| CN101987879A (en) * | 2010-11-05 | 2011-03-23 | 山东鲁抗立科药物化学有限公司 | Macroporous quaternary ammonium type epoxy carrier resin and preparation method thereof |
| CN102617780A (en) * | 2011-01-28 | 2012-08-01 | 湖州欣和环境科技有限公司 | Synthetic method of enzyme-immobilized resin of load epoxide group |
| CN102690846A (en) * | 2012-05-30 | 2012-09-26 | 广东乐尔康生物科技股份有限公司 | Method for catalytically synthesizing gamma-aminobutyric acid from glutamate biological solid-phase enzyme |
| CN103288991A (en) * | 2013-05-29 | 2013-09-11 | 西北师范大学 | Covalent connecting carrier by taking epoxy group as functional group and preparation method thereof |
| CN112126638A (en) * | 2020-09-27 | 2020-12-25 | 南开大学 | Lipase immobilized resin and preparation method thereof |
| CN113403297A (en) * | 2021-08-03 | 2021-09-17 | 北京诚志高科生物科技有限公司 | D-mannose isomerase immobilized enzyme and preparation method and application thereof |
-
2005
- 2005-05-18 CN CNB2005100135226A patent/CN100564523C/en active Active
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101864410A (en) * | 2010-04-16 | 2010-10-20 | 华东理工大学 | Epoxy mesoporous molecular sieve for use in bio-enzyme immobilization and preparation method thereof |
| CN101987879A (en) * | 2010-11-05 | 2011-03-23 | 山东鲁抗立科药物化学有限公司 | Macroporous quaternary ammonium type epoxy carrier resin and preparation method thereof |
| CN102617780A (en) * | 2011-01-28 | 2012-08-01 | 湖州欣和环境科技有限公司 | Synthetic method of enzyme-immobilized resin of load epoxide group |
| CN102690846A (en) * | 2012-05-30 | 2012-09-26 | 广东乐尔康生物科技股份有限公司 | Method for catalytically synthesizing gamma-aminobutyric acid from glutamate biological solid-phase enzyme |
| CN103288991A (en) * | 2013-05-29 | 2013-09-11 | 西北师范大学 | Covalent connecting carrier by taking epoxy group as functional group and preparation method thereof |
| CN103288991B (en) * | 2013-05-29 | 2015-10-28 | 西北师范大学 | Take epoxy group(ing) as covalently bound carrier of functional group and preparation method thereof |
| CN112126638A (en) * | 2020-09-27 | 2020-12-25 | 南开大学 | Lipase immobilized resin and preparation method thereof |
| CN112126638B (en) * | 2020-09-27 | 2022-04-08 | 南开大学 | Lipase immobilized resin and preparation method thereof |
| CN113403297A (en) * | 2021-08-03 | 2021-09-17 | 北京诚志高科生物科技有限公司 | D-mannose isomerase immobilized enzyme and preparation method and application thereof |
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| Publication number | Publication date |
|---|---|
| CN100564523C (en) | 2009-12-02 |
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