CN108588150A - Batch feeding-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method - Google Patents
Batch feeding-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method Download PDFInfo
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Abstract
Batch feeding oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, is related to the preparation method of low-molecular weight chitoglycan.The batch feeding oxidative degradation of chitosan pre-processes, and obtains degradation solution；Hydrogen peroxide removes；The enzymatic hydrolysis of chitosan inhibits with side reaction；Product detaches and drying, obtains chitosan oligosaccharide.Concentration of substrate in degradation of chitosan system is improved by batch feeding mode in oxidation pre-treatment, initial hydrolysis is realized, so that chitosan is further hydrolyzed eventually by the effect of enzyme.With the highly concentrated Hydrolyze method of chitosan of early development comparatively, preprocess method has equipment simple, adaptable, it is easy to be combined with technologies such as enzyme mebrane reactor, immobilised enzymes, has larger application prospect in terms of the chitosan oligosaccharide of preparation Narrow Molecular Weight Distribution.
Description
Technical field
The present invention relates to the preparation methods of low-molecular weight chitoglycan, are assisted more particularly, to batch feeding-oxidation pre-treatment
The method that enzyme hydrolysis chitosan prepares chitosan oligosaccharide.
Background technology
Chitosan is by Glucosamine and acetylglucosamine linear big point by β-Isosorbide-5-Nitrae glucosides key connection
Son, molecular weight are differed from hundreds of thousands to millions of, are unique naturally occurring positively charged glycan in nature, neutral and
It is insoluble in alkaline solution, it can not dissolve in organic solvent, although solvable in acidic aqueous solution, solubility is limited,
And viscosity is high, seriously affects the application of chitosan.Low-molecular weight chitoglycan is the incomplete hydrolysate of chitosan, is retained
There are the fundamental characteristics such as characterization of adsorption, positive charge characteristic, reproducibility and the alkalinity of chitosan, while having dissolubility good, viscous again
The advantages that low, bioactivity is high is spent, especially potential application of the chitosan oligosaccharide in antitumor drug and in terms of improving immunity causes
The extensive concern of domestic and international researcher.Low-molecular weight chitoglycan as a kind of functional sugar, agricultural, medicine, functional food,
The fields such as material have broad application prospects.
The biodegrading process of chitosan mainly has Physical, chemical method, enzyme process and various united hydrolysis methods.Physical is such as common
γ radiation methods be easy to happen chitosan crosslinked and disproportionation side reaction in degradation process, influence further to degrade, and large-scale spoke
Jet device increases production cost.Chemical method is to destroy β-Isosorbide-5-Nitrae glycosidic bond using strong acid or oxidant to realize hydrolysis, the method valence
Lattice are cheap, especially using hydrogen peroxide be the oxidative degradation process of oxidant with no residual hazard, cleaning, efficiently etc. advantages.But it is logical
Chemical method is crossed to prepare chitosan oligosaccharide there is also prodigious drawbacks.If acid-hydrolysis method hydrolytic process is difficult to control, product is mainly monosaccharide
With the lower product of bioactivity such as disaccharides, and a large amount of acid is unfavorable to the purifying of late-stage products and liquid waste processing；Hydrogen peroxide
Oxidative degradation chitosan is further degraded and is deposited for preparing low-molecular weight chitoglycan of the molecular weight higher than 10000 advantageously
In product " peroxidating " problem, i.e. product structure occurs significant change, therefore is difficult to obtain oligopolymerization chitosan only by chemical method
Sugar.Enzyme process, which is a kind of mild method, the especially chitosan enzyme of specificity, can produce the oligosaccharide product for being practically free of monosaccharide.
But specificity enzyme preparation is of high cost, thermal stability is poor, it is difficult to large-scale application；In addition, the high viscosity of chitosan solution is very big
The collision for hindering enzyme molecule and chitosan macromolecular is unfavorable for effective shearing of enzyme.It is experimentally confirmed that when chitosan concentration is higher than
When 5% (mass volume ratio), chitosan dissolving is slow, it is difficult to form uniform system, and viscosity is high, dispersibility is very poor.Shell
The low concentration hydrolysis of glycan causes energy consumption, water consume high, and utilization rate of equipment and installations is low, post-processing trouble etc..Therefore, degradation of chitosan system
Low concentration, high viscosity be still to hinder the maximum bottleneck that efficiently produces of low-molecular weight chitoglycan.Chinese patent
The 201010172203.0 a kind of methods for disclosing quick dissolving chitosan, chitosan oligosaccharide being prepared with high concentration substrate enzymatic, using height
Speed shearing dispersion machine auxiliary dissolving chitosan, makes degradation of chitosan by way of gradually adding chitosan, acetic acid and hydrolase
Final substrate concentrations reach 10%~20% in system.But this method needs that the work of enzyme may be influenced using high-speed dispersion equipment
Property, in addition, the lasting high viscosity systems of degradation process are unfavorable for conversion and the molecule diffusion of enzyme texture image, therefore the technique
(20~80U/g) more demanding to enzymatic activity and dosage, production cost is higher.
Invention content
It is an object of the invention to can to overcome in existing chitosan oligosaccharide production technology that there are viscosity high, concentration of substrate is low, production
The deficiencies such as efficiency is low, provide the method that batch feeding-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide.
The present invention includes the following steps：
1) batch feeding of chitosan-oxidative degradation pretreatment, obtains degradation solution；
In step 1), the pretreated method of batch feeding-oxidative degradation of the chitosan can be：By Chitosan powder
It is dispersed in water, acid dissolving is added, add hydrogen peroxide reaction, acid and chitosan are added in batches, until chitosan concentration reaches
6%~30%；It is described to be dispersed in water Chitosan powder, Chitosan powder is scattered in 25~50 times of water by mass volume ratio
In, wherein Chitosan powder by mass, calculate by volume by water；The addition acid dissolving can be according to 0.25~0.35mL acid/g
Chitosan；It can be 0.5%~10% that quality final concentration, which can be added, in the hydrogen peroxide；The temperature of the reaction can be 40~70 DEG C；
The pretreated time can be 10~60min；Acetic acid can be used in the acid；It is described to add acid and chitosan in batches, it can be each
The chitosan amount added is no more than the initial incremental amount of chitosan, and each feed supplement time interval is 5~10min, makes chitosan most
Final concentration reaches 6%~30%；After oxidative degradation, using the hydrogen peroxide in catalase removing system until starch-
The constant indigo plant of potassium iodide starch paper, hydrogen peroxide enzyme dosage are 0.0015~0.003g/mL.
2) hydrogen peroxide removes；
In step 2), the method for the hydrogen peroxide removing can be：Hydrogen peroxide is added in degradation solution obtained by step 1)
The remaining hydrogen peroxide of enzyme removing, dosage is 0.0015~0.003g/mL pretreatment fluids, until liquid cannot be such that KI- starch papers become
It is blue.
3) enzymatic hydrolysis of chitosan inhibits with side reaction；
In step 3), the method that the enzymatic hydrolysis of the chitosan inhibits with side reaction can be：With ammonium hydroxide, sodium hydroxide
Or a kind of set-up procedure 2 in potassium hydroxide solution) gained liquid pH value 4~6, add according to the 1%~20% of chitosan mass
Shell adding endohydrolase, enzymolysis process are brown by adding a kind of inhibition in sodium hydrogensulfite, sodium sulfite, sodium pyrosulfite etc.
Becoming reaction, the dosage of inhibitor is 0.05~0.15g/g chitosans, 40~60 DEG C of reaction temperature, the reaction time 4~for 24 hours, until
Required molecular weight；It is 5~10M that mass concentration, which can be used, in the ammonium hydroxide, sodium hydroxide or potassium hydroxide solution；The enzyme includes shell
One kind in dextranase, cellulase, hemicellulase etc..
4) product separation and drying, obtain chitosan oligosaccharide.
In step 4), the product separation can be with dry method：With ammonium hydroxide, sodium hydroxide or potassium hydroxide solution
In a kind of set-up procedure 3) gained liquid pH value to 7, removes enzyme using 10~20kDa ultrafiltration membranes, chitosan oligosaccharide obtained after dry,
The chitosan oligosaccharide is light yellow chitosan oligosaccharide product, and deacetylating degree of chitosan is 80%~100%；It is dry that spraying can be used in the drying
One kind in dry, freeze-drying, vacuum drying etc..
The present invention improves concentration of substrate in degradation of chitosan system in oxidation pre-treatment by batch feeding mode,
It realizes initial hydrolysis, so that chitosan is further hydrolyzed eventually by the effect of enzyme.With the highly concentrated Hydrolyze method of chitosan of early development
Comparatively, the present invention relates to preprocess method have equipment it is simple, adaptable, be easy to enzyme mebrane reactor, fixation
Change the technologies such as enzyme to be combined, has larger application prospect in terms of the chitosan oligosaccharide for preparing Narrow Molecular Weight Distribution.The content of present invention pair
Efficient, the green production of chitosan oligosaccharide are of great significance.
The present invention has the following advantages：
1) batch feeding oxidation pre-treatment method viscosity reduction, enrichment effect are good, and method applicability is strong, be easy to enzyme mebrane reactor,
Fixation techniques for enzyme is coupled, and has larger application prospect in terms of the chitosan oligosaccharide for preparing Narrow Molecular Weight Distribution；
2) chemical reagent that this method uses is few, and pollution is few, and Product safety is high, meets Green Chemistry production theory；
3) entirely degradation system reaction condition is mild, and consersion unit is simple, is easily enlarged production.
Description of the drawings
Fig. 1 is chitosan molecular weight of product distribution situation after peroxidating-enzymic degradation obtained by the embodiment of the present invention.Scheming
In 1, (a) is 6% chitosan；(b) it is 9% chitosan.
Specific implementation mode
Following embodiment will be described in detail the specific implementation mode of the present invention in conjunction with attached drawing.
Embodiment 1
3g chitosans are dispersed in 96mL water, 1mL glacial acetic acid are added, at room temperature stirring and dissolving, then add 4mL
30% hydrogen peroxide, is stirred to react 5min at 60 DEG C, adds 1mL glacial acetic acid and 3g chitosans, control pretreatment total time rapidly
1h, addition 0.2g catalases remove hydrogen peroxide, and pH value is adjusted with concentrated ammonia liquor, and 5g cellulases are added, anti-in 55 DEG C of shaking tables
12h is answered, it is 7 that the degradation solution ammonium hydroxide of acquisition, which adjusts pH value, removes enzyme using 10kDa ultrafiltration membranes, filtrate is dry by vacuum refrigeration
It is dry to obtain light yellow chitosan oligosaccharide product, wherein the chitosan oligosaccharide yield that can be dissolved in 75% ethyl alcohol reaches 90%.Product is carried out
TLC identification is shown in that Fig. 1 (a), S are standard items, and 1~4 is respectively that same sample is repeated 4 times.Standard items from top to bottom 7
Point is respectively GlcN：Glucosamine；(GlcN)2：Chitobiose；(GlcN)3：Chitotriose；(GlcN)4：Shell tetrose；(GlcN)5：
Shell pentasaccharides；(GlcN)6：Six sugar of shell；(GlcN)7：Seven sugar of shell.
Embodiment 2
According to embodiment 1,1mL glacial acetic acid and 3g chitosans, control pretreatment are added respectively pre-processing the 5th and 15min
Total time 0.5h, addition 0.2g catalases remove hydrogen peroxide, adjust pH value with concentrated ammonia liquor, 5g cellulases are added, in 55
DEG C shaking table reacts 6h, and product can dissolve under the conditions of pH7~14, and the reaction was continued to 12h, the degradation solution ammonium hydroxide tune of acquisition
It is 7 to save pH value, and enzyme is removed using 10kDa ultrafiltration membranes, and filtrate obtains light yellow chitosan oligosaccharide product by vacuum freeze drying, wherein
The chitosan oligosaccharide yield that 75% ethyl alcohol can be dissolved in reaches 70%.TLC identification is carried out to product, sees Fig. 1 (b).S is mark
Quasi- product；5~8 be respectively that same sample is repeated 4 times.From top to bottom 7 points are respectively GlcN to standard items：Glucosamine；
(GlcN)2：Chitobiose；(GlcN)3：Chitotriose；(GlcN)4：Shell tetrose；(GlcN)5：Shell pentasaccharides；(GlcN)6：Six sugar of shell；
(GlcN)7：Seven sugar of shell.
Embodiment 3
According to embodiment 2,1.2g NaHSO are added in when enzymolysis3, 12h is digested, almost lily chitosan oligosaccharide is obtained, wherein
The chitosan oligosaccharide yield that 75% ethyl alcohol can be dissolved in reaches 48%.
Claims (10)
1. batch feeding-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, it is characterised in that including following step
Suddenly：
1) batch feeding of chitosan-oxidative degradation pretreatment, obtains degradation solution；
2) hydrogen peroxide removes；
3) enzymatic hydrolysis of chitosan inhibits with side reaction；
4) product separation and drying, obtain chitosan oligosaccharide.
2. batch feeding as described in claim 1-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, feature
It is in step 1), the pretreated method of batch feeding-oxidative degradation of the chitosan is：Chitosan powder is scattered in
In water, acid dissolving is added, adds hydrogen peroxide reaction, adds acid and chitosan in batches, until chitosan concentration reaches 6%~
30%.
3. batch feeding as claimed in claim 2-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, feature
Be it is described Chitosan powder is dispersed in water, Chitosan powder is scattered in 25~50 times of water by mass volume ratio,
Middle Chitosan powder by mass, calculate by volume by water.
4. batch feeding as claimed in claim 2-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, feature
It is that the addition acid dissolving is according to 0.25~0.35mL acid/g chitosans；The hydrogen peroxide is that addition quality is final concentration of
0.5%~10%；The temperature of the reaction is 40~70 DEG C；The pretreated time is 10~60min.
5. batch feeding as claimed in claim 2-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, feature
It is that the acid uses acetic acid；It is described to add acid and chitosan in batches, it is that the chitosan amount added every time is no more than chitosan
Initial incremental amount, each feed supplement time interval are 5~10min, and chitosan ultimate density is made to reach 6%~30%；Oxidative degradation
After, using the hydrogen peroxide in catalase removing system until the constant indigo plant of starch-kalium iodide test paper, catalase are used
Amount is 0.0015~0.003g/mL.
6. batch feeding as described in claim 1-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, feature
It is in step 2), the method for the hydrogen peroxide removing is：The addition catalase removing in degradation solution obtained by step 1)
Remaining hydrogen peroxide, dosage are 0.0015~0.003g/mL pretreatment fluids, until liquid cannot make KI- starch papers become blue.
7. batch feeding as described in claim 1-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, feature
It is in step 3), the method that the enzymatic hydrolysis of the chitosan inhibits with side reaction is：With ammonium hydroxide, sodium hydroxide or hydrogen-oxygen
Change a kind of set-up procedure 2 in potassium solution) gained liquid pH value 4~6, it is poly- according to 1%~20% addition shell of chitosan mass
Glycosylhydrolase, enzymolysis process are reacted by a kind of Restrain browning added in sodium hydrogensulfite, sodium sulfite, sodium pyrosulfite,
The dosage of inhibitor is 0.05~0.15g/g chitosans, 40~60 DEG C of reaction temperature, reaction time 4~for 24 hours, until required point
Son amount.
8. batch feeding as claimed in claim 7-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, feature
It is that the ammonium hydroxide, sodium hydroxide or potassium hydroxide solution use mass concentration for 5~10M；The enzyme includes chitosan enzyme, fibre
One kind in the plain enzyme of dimension, hemicellulase.
9. batch feeding as described in claim 1-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, feature
It is in step 4), the product separation is with dry method：With one in ammonium hydroxide, sodium hydroxide or potassium hydroxide solution
Kind of set-up procedure 3) gained liquid pH value to 7, removes enzyme using 10~20kDa ultrafiltration membranes, chitosan oligosaccharide obtained after dry.
10. batch feeding as claimed in claim 9-oxidation pre-treatment auxiliary enzymes hydrolyzing chitosan prepares chitosan oligosaccharide method, special
Sign is described dry one kind using in spray drying, freeze-drying, vacuum drying.
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| CN110305916A (en) * | 2019-07-22 | 2019-10-08 | 厦门大学 | A kind of preparation method of the fluorescent material based on chitosan oligosaccharide Maillard reaction |
| CN110627712A (en) * | 2019-09-29 | 2019-12-31 | 华中农业大学 | Application of 5-hydroxy-2 pyridine methanol isomer as browning marker of chitooligosaccharide |
| CN110642676A (en) * | 2019-10-09 | 2020-01-03 | 上海泾维化工科技有限公司 | Method for producing 1,2, 4-butanetriol |
| CN114438150A (en) * | 2022-04-11 | 2022-05-06 | 中国海洋大学 | Method for inhibiting browning of chitosan oligosaccharide |
| CN115521960A (en) * | 2022-09-20 | 2022-12-27 | 山东海锋生物工程有限公司 | Production process for reducing non-enzymatic browning of chitosan oligosaccharide |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109975282A (en) * | 2019-04-04 | 2019-07-05 | 华侨大学 | A kind of spectrophotometry based on enzymatic potassium iodide oxidative color-developing detection content of hydrogen peroxide |
| CN110305916A (en) * | 2019-07-22 | 2019-10-08 | 厦门大学 | A kind of preparation method of the fluorescent material based on chitosan oligosaccharide Maillard reaction |
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| CN114438150A (en) * | 2022-04-11 | 2022-05-06 | 中国海洋大学 | Method for inhibiting browning of chitosan oligosaccharide |
| CN115521960A (en) * | 2022-09-20 | 2022-12-27 | 山东海锋生物工程有限公司 | Production process for reducing non-enzymatic browning of chitosan oligosaccharide |
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