CN100584955C - Chitosan oligosaccharide/chito-oligomer single enzyme production process - Google Patents
Chitosan oligosaccharide/chito-oligomer single enzyme production process Download PDFInfo
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- CN100584955C CN100584955C CN200610166594A CN200610166594A CN100584955C CN 100584955 C CN100584955 C CN 100584955C CN 200610166594 A CN200610166594 A CN 200610166594A CN 200610166594 A CN200610166594 A CN 200610166594A CN 100584955 C CN100584955 C CN 100584955C
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- enzyme
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- chitooligosaccharide
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 13
- 102000004190 Enzymes Human genes 0.000 title claims abstract description 13
- RQFQJYYMBWVMQG-IXDPLRRUSA-N chitotriose Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](CO)O1 RQFQJYYMBWVMQG-IXDPLRRUSA-N 0.000 title 1
- 229920001661 Chitosan Polymers 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 150000001768 cations Chemical class 0.000 claims abstract description 7
- 239000011347 resin Substances 0.000 claims abstract description 7
- 229920005989 resin Polymers 0.000 claims abstract description 7
- 108010093096 Immobilized Enzymes Proteins 0.000 claims abstract description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 5
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- 238000001976 enzyme digestion Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 238000009288 screen filtration Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000007857 degradation product Substances 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 abstract description 3
- 238000006731 degradation reaction Methods 0.000 abstract description 3
- 101710136247 Endo-chitosanase Proteins 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- 108010089807 chitosanase Proteins 0.000 description 5
- 230000002255 enzymatic effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000003912 environmental pollution Methods 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 3
- 229960002442 glucosamine Drugs 0.000 description 3
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000002144 chemical decomposition reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 239000004382 Amylase Substances 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 108010064696 N,O-diacetylmuramidase Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention is a chitooligosaccharide/chito oligomer production process by specific enzyme, firstly preparing 1-6% chitosan solution, adding in saturated sodium bicarbonate solution to regulate pH value, adding in endo-chitosanase for enzymic hydrolysis, then adopting macroporous weakly acidic cation resin chromatographic column to separate and purify the degraded product- chitooligosaccharide, and after reaction ends, adopting screen filter method to recover immobilized enzyme, adopting ultrafiltration membrane to recover dissociative enzyme, and able to use repeatedly. And the process can make high efficiency specific degradation on chitosan, extremely raising yield of chitooligosaccharide, having featuring of simple production process, largely reduced production cost, and effectively improved quality of chitooligosaccharide product. And the whole production process is a continous production process, which meets the requirements for industrialized large-scale production of chitooligosaccharide product.
Description
Technical field
The present invention relates to the specificity enzymatic production process of a kind of oligochitosan/shell oligomer.
Background technology
Oligochitosan is the solubility small molecules chitosan of the glucosamine polymerization degree in 2≤n 〉=10 scopes, and the shell oligomer is a polymerization degree n greater than 10 soluble chitosan.Oligochitosan and shell oligomer are the key intermediates of chitosan serial application product, possess good water solubility, biological activity height, function various, easily be absorbed by the body, have great application prospect in fields such as medicine, food, daily use chemicals, industrial or agricultural, have the good reputation of the sixth-largest vital principle of human body, soft gold at home and abroad.
Chemical degradation method and non-specificity combined-enzyme method are mainly adopted in the preparation of oligochitosan at present.Adopt the chemical method degrade chitosan, product oligochitosan yield is low, the product separation difficulty, and environmental pollution is serious, is eliminated gradually in recent years.The enzyme liberating method has the reaction conditions gentleness, and oligochitosan yield height does not cause advantages such as environmental pollution, is the main direction of present industrialization degrade chitosan production development.But it is to adopt non-specificity prozyme basically that existing enzyme process prepares the technology of oligochitosan, as lipase, amylase, N,O-Diacetylmuramidase, proteolytic ferment etc., main drawback is: non-specificity, degradation efficiency is low, the molecular weight distribution of oligochitosan product is inhomogeneous, physiologically active is inconsistent, does not reach domestic and international food, the medical market demand to high-quality oligochitosan intermediate, has therefore seriously hindered the producing and selling and the application of oligochitosan.
Summary of the invention
Purpose of the present invention just provides the specificity enzymatic production process of a kind of oligochitosan/shell oligomer, and this art production process is simple, cost is low, oligochitosan yield height, the relative homogeneous of oligochitosan molecular size, quality controllable, and non-environmental-pollution.
The specificity enzymatic production process of oligochitosan of the present invention/shell oligomer is:
1, at first with chitosan with 1～2% dilute acetic acid, be made into 1～6% chitosan solution; 2,, add saturated sodium bicarbonate solution and regulate pH value to 5.8～6 according to the needs of enzymolysis; 3, add the inscribe chitoanase and carry out enzymolysis, inscribe chitoanase add-on is 1～10U/g chitosan, described inscribe chitoanase (eCSN, molecular weight 25KDa) is a kind of inscribe chitoanase that derives from fungi, can specificity cut off the β-1 of chitosan, 4 glycosidic links, the pattern of inscribe chitosanase preparation, it can be the enzyme of unbound state, also can be immobilized enzyme, the enzyme digestion reaction temperature be at 30～60 ℃, and the enzyme digestion reaction time can (need the molecular weight of shell oligomer more little for 2～12 hours, then the reaction times long more, can regulate control voluntarily); 4, adopt macropore acidulous cation resin chromatography column that the degradation products oligochitosan is carried out separation and purification, concrete grammar be with sample on the enzymolysis solution to chromatography column, last sample volume is 5%～50%, adopts 0～3mol/L ammoniacal liquor wash-out again, perhaps the hydrochloric acid soln wash-out of 0～3mol/L concentration reclaims product; 5, after reaction finishes, adopt the method for screen filtration to reclaim immobilized enzyme, the method for employing ultrafiltration membrance filter reclaims the enzyme of unbound state, can recycle.
The specificity enzymatic production process of oligochitosan of the present invention/shell oligomer adopts narrow spectrum inscribe chitoanase, can carry out high efficiency specificity degraded to chitosan, improved the yield of oligochitosan greatly, production process is simple, production cost descends significantly, and product does not contain monose (glucosamine), has improved the quality of oligochitosan product effectively, whole process of production is serialization production, has satisfied the requirement of the large-scale industrialization production of oligochitosan product.This technology and chemical degradation or non-specificity enzymic degradation technology relatively have very big advantage:
1, the relative homogeneous of oligochitosan molecular size of Production by Enzymes is quality controllable;
2, the working condition gentleness is free from environmental pollution;
3, the oligochitosan yield height (95.9%) of Production by Enzymes;
4, do not contain monose (glucosamine) in the finished product.
Embodiment
Embodiment 1
3% chitosan is dissolved in the acetic acid of 1% concentration, regulate pH to 5.8 with saturated sodium bicarbonate solution, press 5U/g and add immobilization inscribe chitosanase preparation, immobilization inscribe chitosanase preparation is by Jiangxi Normal University's chitosan development of resources and utilize project team to provide; The enzyme digestion reaction temperature is 45 ℃, and the enzyme digestion reaction time is 3 hours; Adopt the method for screen filtration to reclaim immobilized enzyme, and obtain the enzymolysis supernatant liquor; The enzymolysis supernatant liquor that adds 30% column volume in macropore acidulous cation resin D155 chromatography column upper end, 0～3mol/L ammoniacal liquor gradient elution, collection and the reducing sugar that whether contains with DNS (3, the 5-dinitrosalicylic acid) reagent detection elutriant; Be not degraded into the white precipitate that the bigger constituent of chitosan of the molecular weight of oligochitosan forms in the elutriant as yet, can direct filtration reclaim, carry out enzymolysis again; Collect DNS reagent and detect the elutriant that male contains oligochitosan, the elutriant water white transparency illustrates that macropore acidulous cation resin D155 has the ability of adsorpting pigment, so can save oligochitosan this purification step that decolours; Adopt the shell and tube thin-film evaporator to concentrate the elutriant that contains oligochitosan, ammonia wherein is volatile matter, can absorb with deionized water to utilize again; Spissated oligochitosan solution spray or lyophilize obtain the oligochitosan product.
Embodiment 2
3% chitosan is dissolved in the acetic acid of 1% concentration, regulate pH to 5.8 with saturated sodium bicarbonate solution, press the inscribe chitosanase preparation that 5U/g adds free state, the inscribe chitosanase preparation of free state is by Jiangxi Normal University's chitosan development of resources and utilize project team to provide; The enzyme digestion reaction temperature is 45 ℃, and the enzyme digestion reaction time is 3 hours; Adopt the method for ultrafiltration membrance filter to reclaim the enzyme of unbound state, and obtain the enzymolysis supernatant liquor; The enzymolysis supernatant liquor that adds 30% column volume in macropore acidulous cation resin D155 chromatography column upper end, 0～3mol/L ammoniacal liquor gradient elution, collection and the reducing sugar that whether contains with DNS reagent detection elutriant; Be not degraded into the white precipitate that the bigger constituent of chitosan of the molecular weight of oligochitosan forms in the elutriant as yet, can direct filtration reclaim, carry out enzymolysis again; Collect DNS reagent and detect the elutriant that male contains oligochitosan, the elutriant water white transparency illustrates that macropore acidulous cation resin D155 has the ability of adsorpting pigment, so can save oligochitosan this purification step that decolours; Adopt the shell and tube thin-film evaporator to concentrate the elutriant that contains oligochitosan, ammonia wherein is volatile matter, can absorb with deionized water to utilize again; Spissated oligochitosan solution spray or lyophilize obtain the oligochitosan product.
Claims (1)
1, the specificity Production by Enzymes method of a kind of oligochitosan/shell oligomer is characterized in that: said method comprising the steps of:
(1), at first with chitosan with 1～2% dilute acetic acid, be made into 1～6% chitosan solution;
(2), according to the needs of enzymolysis, add saturated sodium bicarbonate solution and regulate pH value to 5.8～6;
(3), add the inscribe chitoanase and carry out enzymolysis, inscribe chitoanase add-on is 1～10U/g chitosan, the enzyme digestion reaction temperature is at 30～60 ℃, and the enzyme digestion reaction time can be 2～12 hours, and the preparation pattern of described inscribe chitoanase is unbound state enzyme or immobilized enzyme;
(4), adopt macropore acidulous cation resin chromatography column that the degradation products oligochitosan is carried out separation and purification, to chromatography column, last sample volume is 5%～50% with sample on the enzymolysis solution, adopts 0～3mol/L ammoniacal liquor wash-out again, perhaps the hydrochloric acid soln wash-out of 0～3mol/L concentration reclaims product;
(5), after reaction finishes, adopt screen filtration to reclaim immobilized enzyme, adopt ultrafiltration membrance filter to reclaim the enzyme of unbound state.
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| Application Number | Priority Date | Filing Date | Title |
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| CN200610166594A CN100584955C (en) | 2006-12-27 | 2006-12-27 | Chitosan oligosaccharide/chito-oligomer single enzyme production process |
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| Application Number | Priority Date | Filing Date | Title |
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| CN200610166594A CN100584955C (en) | 2006-12-27 | 2006-12-27 | Chitosan oligosaccharide/chito-oligomer single enzyme production process |
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| CN101024850A CN101024850A (en) | 2007-08-29 |
| CN100584955C true CN100584955C (en) | 2010-01-27 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101619082B (en) * | 2008-07-01 | 2011-08-10 | 中国科学院大连化学物理研究所 | Method for separating and purifying chitosan oligosaccharide monomer |
| CN102994489B (en) * | 2012-10-09 | 2014-01-08 | 山西农业大学 | Biotin-avidin system immobilized glucoamylase and preparation method thereof |
| CN105861597A (en) * | 2016-06-01 | 2016-08-17 | 青岛科海生物有限公司 | Novel marine polysaccharide-chitooligosaccharide production technique |
| CN111171182B (en) * | 2020-03-02 | 2020-09-01 | 江西师范大学 | Method for preparing chitosan oligosaccharide monomer by modifying chitosan oligosaccharide with aromatic aldehyde |
| CN113293185A (en) * | 2021-04-02 | 2021-08-24 | 上海应用技术大学 | Preparation method of chitosan oligosaccharide |
| CN117238447B (en) * | 2023-11-16 | 2024-06-14 | 山东卫康生物医药科技有限公司 | Medical functional food production monitoring and adjusting system |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1724659A (en) * | 2005-06-14 | 2006-01-25 | 浙江大学 | Preparation method of chitin incision enzyme |
| CN1746193A (en) * | 2005-09-15 | 2006-03-15 | 武汉大学 | Preparation of low-molecular weight chitoglycan or chitooligose |
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- 2006-12-27 CN CN200610166594A patent/CN100584955C/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1724659A (en) * | 2005-06-14 | 2006-01-25 | 浙江大学 | Preparation method of chitin incision enzyme |
| CN1746193A (en) * | 2005-09-15 | 2006-03-15 | 武汉大学 | Preparation of low-molecular weight chitoglycan or chitooligose |
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| CN101024850A (en) | 2007-08-29 |
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