CN108913735A - A method of chitosan oligosaccharide is prepared using lipase - Google Patents
A method of chitosan oligosaccharide is prepared using lipase Download PDFInfo
- Publication number
- CN108913735A CN108913735A CN201810880370.7A CN201810880370A CN108913735A CN 108913735 A CN108913735 A CN 108913735A CN 201810880370 A CN201810880370 A CN 201810880370A CN 108913735 A CN108913735 A CN 108913735A
- Authority
- CN
- China
- Prior art keywords
- lipase
- chitosan
- chitosan oligosaccharide
- solution
- oligosaccharide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention belongs to oligosaccharide preparation technical fields, and in particular to a method of chitosan oligosaccharide is prepared using lipase.The method provided by the invention for preparing chitosan oligosaccharide using lipase, including dissolving the chitosan in acetic acid-sodium acetate buffer solution and adding sucrose fatty ester, prepare chitosan solution, fatty enzyme solution enzymatic hydrolysis is added into chitosan solution, enzymolysis liquid is dialysed after the completion of enzymatic hydrolysis, drying and other steps will be carried out after the concentration of gained dialyzate.The method provided by the invention for preparing chitosan oligosaccharide using lipase is easy to operate, and quickly, short the time required to preparation, obtained catabolite chitosan oligosaccharide yield height, even molecular weight distribution, quality are consistent.
Description
Technical field
The invention belongs to oligosaccharide preparation technical fields, and in particular to a method of chitosan oligosaccharide is prepared using lipase.
Background technique
Chitosan nickname chitosan belongs to long-chain macromolecule, and poorly water-soluble under physiological condition, solution viscosity is big,
It is dissolved in after weakly acidic solution that form the chitosan gum liquid solution of clear viscous be its most important property, this makes its as biology effect
The application of agent is answered to be very limited.Chitosan oligosaccharide is chitosan by a kind of the low of degree of polymerization lower (2-20) obtained from degradation
Molecularly Imprinted Polymer is connected to a large amount of activity group hydroxy and amino on chain segment molecule, therefore has that molecular weight is low, dissolution
Degree is high, moisture absorbability and moisture retentivity is good, absorbability is strong and has many advantages, such as preferable biocompatibility, while also having anti-inflammatory, enhancing
Immunity reduces the physiological activity such as cholesterol, reducing blood lipid, antitumor, antibacterial, antiviral, removing free radical, anti-oxidant.Therefore,
Chitosan oligosaccharide product has preferable application prospect in fields such as health food, medical treatment, cosmetics, utilizes chitosan for further investigation
The related process for preparing chitosan oligosaccharide has positive effect to chitosan oligosaccharide Related product is advanced optimized.
The method of degradation of chitosan mainly includes chemical method, physical method and enzymatic isolation method at present.It is prepared relative to other two kinds
Method, enzymic degradation chitosan has reaction condition mild and is easy to control, is highly-safe, low in the pollution of the environment and can obtain specific
The advantages that degree of polymerization product.Enzyme is divided into specificity enzyme and non-specific enzyme, and specificity enzyme mainly has chitosan enzyme, chitinase
Deng non-specific enzyme mainly has lipase, cellulase, amylase, pectase, protease etc., and wherein lipase is to act on
Water bios meets personally the lipase of insoluble object, and the relative molecular mass of chitosan can be significantly reduced under the conditions of slightly sour, has aobvious
The degradation of chitosan vigor of work, but compared with other non-specific enzymes, it is opposite for the research of Lipase-promoted Hydrolysis of Chitosan at present
It is less.Therefore the present invention selects lipase to prepare the chitosan oligosaccharide of low polymerization degree, to which easier quick preparation oligomerization can be obtained
Spend the method for chitosan oligosaccharide.
1320123 C of Chinese patent literature CN discloses a kind of method using lipase production low-molecular weight chitoglycan,
Enzyme digestion reaction is carried out under conditions of 5~6h of 10~100g/L of concentration of substrate and reaction time, filter vacuum is concentrated and crosses gel
Chromatographic column obtains low-molecular weight chitoglycan, and this method significantly reduces production cost, but the required reaction time is long, enzyme
Liquid and the time length of air contact are oxidized easily, and inevitably cause to seriously affect to the color of the catabolite in later period.
Tan Peiyi etc. has studied the technique that orthogonal experiment method optimization lipase prepares chitosan oligosaccharide, and determining optimum condition is：Lipase
Additive amount is 1.2g/100mL, and hydrolysis temperature is 50 DEG C, pH value of solution 4.5, enzymolysis time 6h, but the time needed for reacting
Long, yield is lower.102492664 B of Chinese patent literature CN discloses a kind of method for preparing chitosan oligosaccharide using complex enzyme,
Middle complex enzyme includes cellulase, lysozyme, amylase, lipase, glucolase and papain, and this method is effective
Yield is improved, obtained chitosan oligosaccharide product distribution is uniform, but the huge number of required enzyme, and step is complicated.Therefore, it is necessary to
Overcoming current chitosan substrate viscosity to lead to problems such as greatly, yield is lower, the reaction time is long and step is complicated, as people
A kind of novel easy to operate, the reaction time short method for preparing chitosan oligosaccharide using lipase are provided.
Summary of the invention
The purpose of the present invention is intended to overcome the shortcomings of the prior art, provides and a kind of prepares chitosan oligosaccharide using lipase
Method, with easy to operate, the reaction time is short, yield is high, obtained catabolite chitosan oligosaccharide even molecular weight distribution etc.
Advantage.In order to achieve the above technical purposes, the technical scheme is that：
A method of chitosan oligosaccharide being prepared using lipase, specifically includes following steps：
S1 dissolution：Acetic acid-sodium acetate buffer solution of pH value 4.0~5.0 is dissolved the chitosan in, sucrose-fatty is added
Ester is made into the chitosan solution that mass concentration is 1.0~2.0%；
S2 lipase hydrolysis：The fatty enzyme solution that concentration is 0.5% is added into the resulting chitosan solution of step S1, makes enzyme
Bottom mass ratio is 20~30%, 40~50 DEG C of 0.5~1.5h of water bath with thermostatic control, obtains enzymolysis liquid, after taking-up boiling water bath 10 minutes into
Row inactivation, is cooled to room temperature；
S3 adjusts pH and dialysis：Into enzymolysis liquid obtained in step S2 be added dropwise mass concentration be 5%NaOH solution simultaneously
PH value is adjusted to 7.0~8.0, water-insoluble chitosan is precipitated, takes filtrate to discard filter residue after filtering, by filtrate regenerated fiber
Plain bag filter is dialysed for 24 hours, and a dialyzate is changed in 8 hours in interval；
Dialyzate obtained in step S3 is concentrated S4, is dried, and chitosan oligosaccharide is made, and the chitosan oligosaccharide quality is uniform
Unanimously.
Further, the pH value of the acetic acid-sodium acetate buffer solution is 4.5.
Further, the additive amount of the sucrose fatty ester is the 0.1~0.5% of chitosan weight.
Further, the HLB value of the sucrose fatty ester is 10~13.
Further, the mass concentration of the chitosan solution is 1.7%.
Further, the fatty enzyme solution is that the acetic acid-sodium acetate buffer solution for being 4.5 by pH value is formulated.
Further, enzyme bottom mass ratio is 22%.
Further, the temperature of the water bath with thermostatic control is 45 DEG C.
Further, the water bath time is 1h.
Further, the molecule interception of the regenerated cellulose bag filter is 3000Da.
Further, the drying means is freeze-drying.
In the inventive solutions, using chitosan as reaction raw materials, chitosan is not soluble in water, lye, You Jirong
Agent, sulfuric acid and phosphoric acid, but acetic acid and dilute hydrochloric acid are dissolved in, this is because its molecular weight is larger, intermolecular and intramolecular exists big
The hydrogen bond of amount leads to its poorly water-soluble.And chitosan is dissolved in the chitosan gum liquid solution of formation clear viscous after acetic acid solution, by
It is sticky in solution, thus lipase is difficult to evenly dispersed in the solution, and substrate is also difficult to the catalytic center knot with lipase
It closes, causes enzymolysis time long, enzymolysis speed is slow, low yield.But it is molten that a large amount of acetic acid is added in order to reduce enzymatic hydrolysis system viscosity
Liquid then will lead to enzymolysis efficiency reduction again, and increased production cost.
Sucrose fatty ester is a kind of nonionic surfactant, is mainly used for emulsifier, antistaling agent, meat products, emulsification
Essence etc.；Meanwhile sucrose fatty ester is also a kind of viscosity reduction auxiliary agent, is widely used in sugar boiling process, for reducing massecuite
Surface tension and viscosity, shortening boil the sugared time, energy saving, increase the sugar rate of recovery.Therefore, inventor attempts in dissolution shell
Sucrose fatty ester is added when glycan, discovery sucrose fatty ester can be effectively reduced the viscosity of chitosan gum liquid solution, obtain
The weak solution of even dispersion.On the one hand, sucrose fatty ester significantly can change or reduce the surface tension of chitosan mucus,
The surface of mucus is set to stretch, to increase its mobility；On the other hand, contain hydrophilic radical in sucrose fatty acid ester,
To destroy the intermolecular hydrogen bond with intramolecular of macromolecular, its dissolubility is improved.But sucrose fatty ester is in a heated condition
It can be saponified, however the optimum pH of lipase is 4.5,45 DEG C of optimum temperature, therefore the sucrose fatty ester in enzymolysis process
It may inactivate, lead to the raising of system viscosity, but it is unexpected that during enzymatic hydrolysis, under system viscosity continues
Drop does not occur the case where viscosity maintains or increases, thus it is speculated that be the combination of chitosan and sucrose fatty ester, improve sucrose
The stability of aliphatic ester, so that it is not saponified in a heated condition.Therefore, the present invention passes through addition chitosan weight 0.1
~0.5% and HLB value be 10~13 sucrose fatty ester, the viscosity of chitosan solution is significantly reduced, to effectively improve
Enzymolysis speed shortens enzymolysis time, improves enzymatic hydrolysis yield.
Compared with prior art, the invention has the advantages that：
(1) present invention is by adding sucrose fatty ester when dissolve chitosan to reduce the viscosity of substrate chitosan,
Then chitosan oligosaccharide is prepared using lipase, the chitosan oligosaccharide that product quality is good, yield is high is finally prepared, prepare shell for lipase
The production of oligosaccharides provides foundation.
(2) method provided by the invention for preparing chitosan oligosaccharide using lipase is simple, and process stabilizing, enzymolysis time is short, enzyme
It is fast to solve speed, obtained chitosan oligosaccharide even molecular weight distribution, quality uniformity, cost is relatively low, is produced on a large scale.
Specific embodiment
The following describes the present invention further through the description of specific embodiments, but it is to limit of the invention that this, which is not,
System, those skilled in the art's basic thought according to the present invention can make various modifications or improvements, but without departing from this
The basic thought of invention, is all within the scope of the present invention.
Chitosan (lot number：171112A, deacetylation > 85%, Shandong aokang Biotechnology Co., Ltd), chitosan oligosaccharide
(lot number：170311C, DD90%, Shandong aokang Biotechnology Co., Ltd), (analysis is pure, in Sigma of U.S. Order for lipase
Odd company), sucrose fatty ester (food-grade, solid, Zhengzhou is abundant and food additives Co., Ltd), regenerated cellulose bag filter
(molecular cut off 3000Da, Town in Shanghai spectrum experiment Science and Technology Co., Ltd.).
The method that embodiment 1, the present invention prepare chitosan oligosaccharide using lipase
S1 dissolution：It dissolves the chitosan in acetic acid-sodium acetate buffer solution of pH value 4.0 and adds chitosan weight
0.1% sucrose fatty ester (HLB value 10) is made into the chitosan solution that mass concentration is 1.0%；
S2 lipase hydrolysis：The fatty enzyme solution that concentration is 0.5% is added into the resulting chitosan solution of step S1, makes enzyme
Bottom mass ratio is 20%, and 40 DEG C of water bath with thermostatic control 0.5h obtain enzymolysis liquid, are inactivated within boiling water bath 10 minutes after taking-up, are cooled to
Room temperature；
S3 adjusts pH and dialysis：The NaOH solution tune that mass concentration is 5% is added dropwise into enzymolysis liquid obtained in step S2
PH value is saved to 7.0~8.0, water-insoluble chitosan is precipitated, takes filtrate to discard filter residue after filtering, by filtrate molecule interception
It is dialysed for 24 hours for the regenerated cellulose bag filter of 3000Da, a dialyzate is changed in 8 hours in interval；
Dialyzate obtained in step S3 is concentrated S4, and is freeze-dried, and obtains chitosan oligosaccharide, and the chitosan oligosaccharide quality is equal
It is even consistent.
Fatty enzyme solution in the step S2 is formulated by acetic acid-sodium acetate buffer solution of pH value 4.5.
The method that embodiment 2, the present invention prepare chitosan oligosaccharide using lipase
S1 dissolution：It dissolves the chitosan in acetic acid-sodium acetate buffer solution of pH value 4.5 and adds chitosan weight
0.4% sucrose fatty ester (HLB value 12) is made into the chitosan solution that mass concentration is 1.7%；
S2 lipase hydrolysis：The fatty enzyme solution that concentration is 0.5% is added into the resulting chitosan solution of step S1, makes enzyme
Bottom mass ratio is 22%, and 45 DEG C of water bath with thermostatic control 1h obtain enzymolysis liquid, are inactivated within boiling water bath 10 minutes after taking-up, are cooled to room
Temperature；
S3 adjusts pH and dialysis：The NaOH solution tune that mass concentration is 5% is added dropwise into enzymolysis liquid obtained in step S2
PH to 7.0~8.0 is saved, water-insoluble chitosan is precipitated, takes filtrate to discard filter residue after filtering, is with molecular interception amount by filtrate
The regenerated cellulose bag filter of 3000Da is dialysed for 24 hours, and a dialyzate is changed in 8 hours in interval；
Dialyzate obtained in step S3 is concentrated S4, and is freeze-dried, and obtains chitosan oligosaccharide, and the chitosan oligosaccharide quality is equal
It is even consistent.
Fatty enzyme solution in the step S2 is formulated by acetic acid-sodium acetate buffer solution of pH value 4.5.
The method that embodiment 3, the present invention prepare chitosan oligosaccharide using lipase
S1 dissolution：It dissolves the chitosan in acetic acid-sodium acetate buffer solution of pH value 5.0 and adds chitosan weight
0.5% sucrose fatty ester (HLB value 13) is made into the chitosan solution that mass concentration is 2.0%；
S2 lipase hydrolysis：The fatty enzyme solution that concentration is 0.5% is added into the resulting chitosan solution of step S1, makes enzyme
Bottom mass ratio is 30%, and 50 DEG C of water bath with thermostatic control 1.5h obtain enzymolysis liquid, are inactivated within boiling water bath 10 minutes after taking-up, are cooled to
Room temperature；
S3 adjusts pH and dialysis：The solution tune that mass concentration is 5%NaOH is added dropwise into enzymolysis liquid obtained in step S2
PH to 7.0~8.0 is saved, water-insoluble chitosan is precipitated, takes filtrate to discard filter residue after filtering, is with molecular interception amount by filtrate
The regenerated cellulose bag filter of 3000Da is dialysed for 24 hours, and a dialyzate is changed in 8 hours in interval；
Dialyzate obtained in step S3 is concentrated S4, and is freeze-dried, and obtains chitosan oligosaccharide, and the chitosan oligosaccharide quality is equal
It is even consistent.
Fatty enzyme solution in the step S2 is formulated by acetic acid-sodium acetate buffer solution of pH value 4.5.
Comparative example 1
Compared with Example 2, the difference of this comparative example is：Do not add sucrose fatty ester.
Comparative example 2
Compared with Example 2, the difference of this comparative example is：The additive amount of sucrose fatty ester is addition chitosan weight
1%.
Comparative example 3
Compared with Example 2, the difference of this comparative example is：Sucrose-fatty is replaced using the sorbierite of identical additive amount
Ester.
The detection of the reduced sugar of chitosan oligosaccharide made from test example, the method for the present invention, moisture, viscosity and yield
(1) measurement of content of reducing sugar：The measurement of content of reducing sugar uses DNS method.Enzymolysis liquid and DNS reagent is taken to react
Boiling water bath colour developing is carried out, constant volume measures its absorbance with ultraviolet specrophotometer, measurement wavelength is to certain volume after colour developing
485nm.Absorbance is updated in standard curve, content of reducing sugar can be calculated.
(2) measurement of moisture：Powder after drying is collected in glass dish, dries 2h in the baking oven of temperature 50 C, with
The cooling 30min in drier afterwards, then 30min is dried again, it weighs after cooling, repeatedly drying weighing, until 2 weighings difference is less than
The calculation formula of 0.003g, chitosan oligosaccharide aqueous powder is：
In formula：ω1To calculate gained chitosan oligosaccharide moisture；G is the chitosan oligosaccharide quality (mg) for measurement；G' is that drying rear shell is few
Saccharic amount (mg).
(3) measurement of viscosity：Under conditions of 25 DEG C of room temperature, the viscosity of rotary viscosity design determining enzymolysis liquid is utilized.This reality
It tests using NDJ-8S Digital Viscometer, L is used according to the range of viscosities of chitosan0The viscosity number of rotor measurement, the process of measurement
It needs to keep solution temperature constant.The 3000Da chitosan oligosaccharide standard items and experiment gained sample for preparing 1% concentration, use viscosimeter
It measures its viscosity and is compared.
(4) measurement of yield：The yield of chitosan oligosaccharide be the obtained raw material object chitosan mass of product quality and enzymatic hydrolysis it
Between ratio multiplied by absolutely.
In formula：m1For gained sample quality (mg) after spray drying；m0For the raw material object chitosan mass (mg) of enzymatic hydrolysis.
To Examples 1 to 3, the product that comparative example 1~3 obtains is detected, and the results are shown in Table 1：
The testing result of each chitosan oligosaccharide product of table 1
Note：COS3000For the chitosan oligosaccharide raw material of molecular weight 3000
From upper table 1：
(1) compared with comparative example 1, Examples 1 to 3 is added to sucrose fatty ester when chitosan dissolves, the bottom of according to
It is obvious at its viscosity reducing effect known to uniform solution when object dissolves, and its yield relative to when being not added with sucrose fatty ester all
It is significantly improved；In Examples 1 to 3, with the yield of chitosan oligosaccharide made from embodiment 2 and content of reducing sugar highest, therefore implement
Example 2 is highly preferred embodiment of the present invention.
(2) compared with Example 2, the additive amount of sucrose fatty ester is the 1% of chitosan weight in comparative example 2, but its
Yield is not significantly improved, illustrates the additive amount for being further continued for increasing sucrose fatty ester, has no apparent raising to yield
Effect, therefore the additive amount of sucrose fatty ester is suitable in the range of 0.1~0.5%.
(3) compared with Example 2, sucrose fatty ester, discovery are replaced using the sorbierite of identical additive amount in comparative example 3
Its yield reduces, and illustrates the more preferable for the viscosity reducing effect of chitosan of sucrose fatty ester, the yield of obtained chitosan oligosaccharide is higher.
The above-described embodiments merely illustrate the principles and effects of the present invention, and is not intended to limit the present invention.It is any ripe
The personage for knowing this technology all without departing from the spirit and scope of the present invention, carries out modifications and changes to above-described embodiment.Cause
This, institute is complete without departing from the spirit and technical ideas disclosed in the present invention by those of ordinary skill in the art such as
At all equivalent modifications or change, should be covered by the claims of the present invention.
Claims (10)
1. a kind of method for preparing chitosan oligosaccharide using lipase, which is characterized in that include the following steps：
S1 dissolution：Acetic acid-the sodium acetate buffer solution for dissolving the chitosan in pH value 4.0~5.0, then adds sucrose-fatty
Ester is made into the chitosan solution that mass concentration is 1.0~2.0%；
S2 lipase hydrolysis：The fatty enzyme solution that concentration is 0.5% is added into the resulting chitosan solution of step S1, makes enzyme substrate
Amount obtains enzymolysis liquid, goes out within boiling water bath 10 minutes after taking-up than being 20~30%, 40~50 DEG C of 0.5~1.5h of water bath with thermostatic control
It is living, it is cooled to room temperature；
S3 adjusts pH and dialysis：The NaOH solution that mass concentration is 5% is added dropwise into enzymolysis liquid obtained in step S2, adjusts pH
Value is precipitated water-insoluble chitosan, takes filtrate to discard filter residue after filtering, filtrate is dialysed with regenerated cellulose to 7.0~8.0
Bag is dialysed for 24 hours, and a dialyzate is changed in 8 hours in interval；
S4 is dry：Dialyzate obtained in step S3 is concentrated, and dry, chitosan oligosaccharide is made.
2. the method for preparing chitosan oligosaccharide using lipase as described in claim 1, which is characterized in that the acetic acid-sodium acetate
The pH value of buffer solution is 4.5.
3. the method for preparing chitosan oligosaccharide using lipase as described in claim 1, which is characterized in that the sucrose fatty ester
Additive amount be chitosan weight 0.1~0.5%.
4. the method for preparing chitosan oligosaccharide using lipase as described in claim 1, which is characterized in that the sucrose fatty ester
HLB value be 10~13.
5. the method for preparing chitosan oligosaccharide using lipase as described in claim 1, which is characterized in that the chitosan solution
Concentration is 1.7%.
6. the method for preparing chitosan oligosaccharide using lipase as described in claim 1, which is characterized in that the fat enzyme solution be by
Acetic acid-sodium acetate buffer solution that pH value is 4.5 is formulated.
7. the method for preparing chitosan oligosaccharide using lipase as described in claim 1, which is characterized in that enzyme bottom mass ratio is
22%.
8. the method for preparing chitosan oligosaccharide using lipase as described in claim 1, which is characterized in that the temperature of the water bath with thermostatic control
Degree is 45 DEG C.
9. the method for preparing chitosan oligosaccharide using lipase as described in claim 1, which is characterized in that the regenerated cellulose is saturating
The molecule interception for analysing bag is 3000Da.
10. the method for preparing chitosan oligosaccharide using lipase as described in claim 1, which is characterized in that the drying means is
Freeze-drying.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810880370.7A CN108913735B (en) | 2018-08-03 | 2018-08-03 | A method of chitosan oligosaccharide is prepared using lipase |
| PCT/CN2018/105045 WO2020024374A1 (en) | 2018-08-03 | 2018-09-11 | Method for preparing chitosan oligosaccharide by using lipase |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810880370.7A CN108913735B (en) | 2018-08-03 | 2018-08-03 | A method of chitosan oligosaccharide is prepared using lipase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108913735A true CN108913735A (en) | 2018-11-30 |
| CN108913735B CN108913735B (en) | 2019-09-03 |
Family
ID=64397242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810880370.7A Active CN108913735B (en) | 2018-08-03 | 2018-08-03 | A method of chitosan oligosaccharide is prepared using lipase |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN108913735B (en) |
| WO (1) | WO2020024374A1 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1401652A (en) * | 2001-08-14 | 2003-03-12 | 华东理工大学 | Process for industrial production of oligochitose and chitooligose |
| CN101381752A (en) * | 2008-10-17 | 2009-03-11 | 扬州日兴生物科技股份有限公司 | Technique for preparing low chitose and chitosan oligosaccharide |
-
2018
- 2018-08-03 CN CN201810880370.7A patent/CN108913735B/en active Active
- 2018-09-11 WO PCT/CN2018/105045 patent/WO2020024374A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1401652A (en) * | 2001-08-14 | 2003-03-12 | 华东理工大学 | Process for industrial production of oligochitose and chitooligose |
| CN101381752A (en) * | 2008-10-17 | 2009-03-11 | 扬州日兴生物科技股份有限公司 | Technique for preparing low chitose and chitosan oligosaccharide |
Non-Patent Citations (3)
| Title |
|---|
| CHIAPPISI, L.等: "Co-assembly in chitosan–surfactant mixtures: thermodynamics,", 《ADVANCES IN COLLOID AND INTERFACE SCIENCE》 * |
| 周莉等: "羧甲基壳聚糖与表面活性剂复配性能的研究", 《深圳大学学报理工版》 * |
| 隋卫平等: "羧甲基壳聚糖与表面活性剂的相互作用", 《青岛海洋大学学报》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2020024374A1 (en) | 2020-02-06 |
| CN108913735B (en) | 2019-09-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Porto et al. | Immobilization of α-amylase in ultrafine polyvinyl alcohol (PVA) fibers via electrospinning and their stability on different substrates | |
| JP2002543248A5 (en) | ||
| Xie et al. | Preparation of low molecular weight chitosan by complex enzymes hydrolysis | |
| WO2021081999A1 (en) | Low-molecular-weight chondroitin sulfate and preparation method therefor | |
| WO2020038077A1 (en) | Chitosan oligosaccharide prepared by compound enzyme and preparation method for chitosan oligosaccharide | |
| WO2013053071A1 (en) | Production method for preparing high purity mannan oligosaccharide from enzymolysis of hemicellulose | |
| CN106432538A (en) | Method for preparing chitin oligosaccharides, chitooligosaccharides and chitosan oligosaccharides | |
| CN104745659B (en) | The method that oligomeric galactomannan sugar enzymolysis liquid is quickly prepared using guar gum | |
| CN105154496B (en) | A method of specified molecular weight water soluble chitosan is prepared using enzyme process | |
| CN110295208B (en) | Method for improving resistance and yield of resistant dextrin | |
| CN108913735B (en) | A method of chitosan oligosaccharide is prepared using lipase | |
| CN101215593B (en) | Technique for preparing oligomeric chitosan by complex enzyme degradation | |
| Il'ina et al. | Depolymerization of high-molecular-weight chitosan by the enzyme preparation Celloviridine G20x | |
| JP2008075075A (en) | Novel glucan and its preparation method | |
| CN101280330A (en) | Method for preparing chitosan oligosaccharide with trichoderma reesei cellulase | |
| CN115887341B (en) | Red rice enzymolysis extract and preparation method thereof | |
| CN104745657B (en) | The method that guar gum solution prepares oligomeric galactomannan sugar enzymolysis liquid | |
| CN108359700B (en) | Method for preparing artemisia desertorum oligosaccharide through enzymolysis and application of artemisia desertorum oligosaccharide | |
| WO2020048270A1 (en) | Method for preparing chitooligosaccharide using snailase and application thereof | |
| CN108300745B (en) | Method for preparing special modified starch by using complex enzyme | |
| CN111035581B (en) | Method for maintaining stability of sialic acid solution at high temperature and application thereof | |
| AU2017101852A4 (en) | Chitooligosaccharide with a specific structure and preparation method and application thereof | |
| CN107501424A (en) | A kind of method for purifying tamarind seed polysaccharide glue | |
| Anggela et al. | OLIGO-GLUCOMANNAN PRODUCTION FROM PORANG (Amorphophallus oncophyllus) GLUCOMANNAN BY ENZYMATIC HYDROLYSIS USING β-MANNANASE | |
| CN112980904B (en) | Method for preparing tussah pupa oligomeric chitosan by using enzymatic method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |