CN103266153A - Production method of modified chitosan - Google Patents
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- CN103266153A CN103266153A CN2013102388623A CN201310238862A CN103266153A CN 103266153 A CN103266153 A CN 103266153A CN 2013102388623 A CN2013102388623 A CN 2013102388623A CN 201310238862 A CN201310238862 A CN 201310238862A CN 103266153 A CN103266153 A CN 103266153A
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Abstract
The invention belongs to the field of biological engineering and relates to chitosan modification. The chitosan modification comprises the following steps of: adding protein or polypeptide; adding transglutaminase; adjusting the pH value; removing precipitates after full reaction; and desalting and drying for modification. The modified chitosan produced by the technical scheme disclosed by the invention is good in water solubility, does not generate precipitate at the pH value of 3-10, and is small in viscosity. Moreover, the functions including strong adsorption, antibacterial property and the like of the chitosan are kept, and the application prospect is extensive.
Description
Technical field
The invention belongs to bioengineering field, relate in particular to a kind of production method of modified chitosan.
Technical background
Chitosan (chitosan) is to be obtained through deacetylation by the chitin (chitin) that nature extensively exists, and chemical name is poly-dextrose amine (1-4)-2-amino-B-D glucose.Amino has a large amount of positive charges owing to existing in a large number in its macromolecular structure, thereby electronegative all kinds of objectionable impuritiess are had powerful adsorption.Premium propertiess such as the biological functionality of this natural polymer and consistency, blood compatibility, security, microbic resolvability are by all trades and professions extensive concern, have the control cholesterol, suppress bacterium, prevention and control hypertension, absorption and drainage heavy metal, keep physiological functions such as humidity, enhancing immunity, obtained major progress in the applied research of numerous areas such as medicine, food, chemical industry, makeup, water treatment, METAL EXTRACTION and recovery, biochemistry and biomedical engineering.
Yet chitosan can only be dissolved in some rare mineral acids or organic acid, can not be directly soluble in water, and this has limited its application to a great extent.In order to address this problem, people make the chitosan energy water-soluble by adopting serial of methods.As: 1. water-soluble chitosan mineral acid or the organic acid hydrochlorate of various energy, as chitosan hydrochloride, chitosan lactate and Chitosan citrate etc.; 2. making degradation of chitosan by chemistry or biological method is the water-soluble low-molecular weight chitoglycan of energy; 3. chitosan chemical modification object that can be water-soluble, as: cm-chitosan etc.; 4. by chemical reaction the acidylate degree of chitosan is accurately controlled, controlled its acidylate degree 50% ~ 60%.
But all there are some defectives in these methods, though water-soluble as chitosan mineral acid or organic acid hydrochlorate, can precipitate greater than 6.2 o'clock in the pH value and to separate out; The physiologically active of low-molecular weight chitoglycan such as germ resistance, adsorptivity etc. reduce greatly or disappear; There is certain safety issue in the chitosan chemical modification object, and its physiologically active also exists change or forfeiture simultaneously; The acidylate degree of chitosan is accurately controlled not only difficult the realization, also have same problem aspect security and the physiologically active.
Summary of the invention
Low in order to solve the chitosan solvability, the pH value can precipitate greater than 6.2 o'clock to be separated out, problems such as viscosity is big, the invention provides a kind of good water solubility, pH3-10 does not precipitate, viscosity is little, also keeps the modified chitosan production method of functions such as the original strong adsorptivity of chitosan, germ resistance, and concrete technical scheme is as follows:
A kind of production method of modified chitosan, comprise the following step: (1) is got chitosan and is dissolved in organic acid or the inorganic acid solution, regulate pH4.0-6.2, (2) add acry radical donor, add Transglutaminase EC2.3.2.13 again, 25-85 ℃ of fully reaction, regulate pH6.2-7.0, filter and remove precipitation, desalination, drying; Described chitosan or chitosan inorganic acid salt: acry radical donor: the Transglutaminase EC2.3.2.13 mass ratio is=1:0.01-1:0.1; Described adding acry radical donor utilizes the γ-carboxamide groups of its glutamine residue as acry radical donor for adding protein or polypeptide.
Described mineral acid or organic acid soln are hydrochloric acid, acetic acid, lactic acid or the citric acid of 0.1-1mol/L; Described Transglutaminase EC2.3.2.13 is 2000U/g.
In order to reach better effect:
Regulating pH is 6.2;
Described acry radical donor is one or more the mixture in glutin, soybean protein, casein, collagen protein, silk fibroin, the polypeptide, is preferably glutin; Described polypeptide is preferably gsh.
Described chitosan: acry radical donor: the Transglutaminase EC2.3.2.13 mass ratio is 1:0.2:0.1.
Dialysis or ultrafiltration desalination are taked in described desalination; Described drying is spraying drying or vacuum-drying.
Chitosan after the modification is the derivative of poly-dextrose amine (1-4)-2-amino-B-D glucose, can dissolve under the pH3-10 condition.
Glutamine changes ammonia (amine) enzyme; another name: trans-glutaminases; English name: Glutamine trasaminase (TG); can derive from animal; plant and microorganism; it is (or interior) acyl group shift reaction between a kind of catalytic proteins; but its catalytic proteins polypeptide generation intramolecularly and intermolecular generation covalent cross-linking; thereby improve the structure and function of protein; to the character of protein as foaminess; emulsifying property; emulsifying stability; thermostability; effects such as water-retentivity and gel ability are remarkable; and then improve flavours in food products; mouthfeel; quality and outward appearance etc. are widely used at food processing field, can be applicable to the aquatic products processing product; ham; sausage; Noodles; bean curd etc.
The present invention relates to the bio-modification of chitosan, can make chitosan when keeping original absorption, flocculation, function such as antibiotic, water soluble, and can not precipitate greater than 6.2 o'clock in the pH value, its solubility property significantly improves than unmodified chitosan greater than 6.2 o'clock in the pH value, and can reduce the viscosity of chitosan, thereby strengthen the scope of application of chitosan greatly.Its ultimate principle is: the transacylate function of utilizing Transglutaminase EC2.3.2.13; the various materials (protein, peptide etc.) that will contain glutamine or contain glutamine are connected by amido linkage with the primary amine groups of chitosan, thereby reach the purpose of the bio-modification of chitosan.
Technical solution of the present invention is carried out the chitosan bio-modification and is had following beneficial effect:
1, the chitosan good water solubility after the modification, the pH value can not precipitate between 3.0-10.0, can make chitosan when keeping original absorption, flocculation, function such as antibiotic, and the scope of application is wider, is particularly useful for the physiological environment of human body;
3, can reduce the viscosity of chitosan, thereby strengthen the scope of application of chitosan greatly;
4, raw material has characteristics such as biological functionality and consistency, blood compatibility, security, microbic resolvability for using food grade or pharmaceutical grade raw material (TG enzyme, protein and polypeptide etc.), and security is good;
5, enzymatic reaction condition gentleness, reaction efficiency height are environmentally friendly;
6, the modified chitosan of producing by the present invention, keeping original bioactive while of chitosan, owing to have the water-soluble and wideer pH scope of application, and it is more safe and reliable, be particularly useful for the physiological pH environment of human body, it has the big using value of tool in fields such as medical and health, health therapy, food-processing, chemical industry and biotechnology.
Embodiment
Biosynthesizing and the application of embodiment 1 chitosan glutin
The biosynthesizing of chitosan glutin: get chitosan 100 gram, be dissolved in the hydrochloric acid of 0.1-1.0 M (under the mol/L with) (or get 100 gram chitosan hydrochlorides, and soluble in water), with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 4.0-6.2, add glutin 1-100 gram (soluble in water in advance), add TG enzyme 5 grams (2000 U/g), in 25 ℃-85 ℃ reactions 1-48 hour, after reaction finishes, with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 6.2-7.0, cross the elimination precipitation, after dialysis or the ultrafiltration desalination, spraying drying or vacuum-drying, get final product the chitosan glutin.
Embodiment 2
Get chitosan 100 gram, be dissolved in the hydrochloric acid of 0.1-1.0 M (or get 100 gram chitosan hydrochlorides, and soluble in water), with the NaOH of 0.1N or the NaHCO of 0.1N
3Regulate pH6.2.Add the acry radical donor glutin, add 2000 U/g Transglutaminase EC2.3.2.13s again, 25-85 ℃ of fully reaction is after reaction finishes, with the NaOH of 0.1N or the NaHCO of 0.1N
3Regulate pH6.2, filter and remove precipitation, desalination, spraying drying or vacuum-drying; Chitosan or chitosan inorganic acid salt: glutin: the Transglutaminase EC2.3.2.13 mass ratio is=1:0.2:0.1.
Biosynthesizing and the application of embodiment 3 chitosan collagen albumen
Get chitosan 100 gram, be dissolved in the hydrochloric acid of 0.1-1.0 M (or get 100 gram chitosan hydrochlorides, and soluble in water), with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 4.0-6.2, add collagen protein 1-100 gram (soluble in water in advance), add TG enzyme 5 grams, in 25 ℃-85 ℃ reactions 1-48 hour, after reaction finishes, with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 6.2-7.0, cross the elimination precipitation, after dialysis or the ultrafiltration desalination, spraying drying or vacuum-drying, get final product chitosan collagen albumen.
Biosynthesizing and the application of embodiment 4 chitosan soybean proteins
Get chitosan 100 gram, be dissolved in the acetic acid of 0.1-1.0 M (or get 100 gram chitosan acetates, and soluble in water), with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 4.0-6.2, add soybean protein 1-100 gram (soluble in water in advance), add TG enzyme 15 grams, in 25 ℃-85 ℃ reactions 1-48 hour, after reaction finishes, with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 6.2-7.0, cross the elimination precipitation, after dialysis or the ultrafiltration desalination, spraying drying or vacuum-drying, get final product the chitosan soybean protein.
The caseic biosynthesizing of embodiment 5 chitosans and application
Get chitosan 100 gram, be dissolved in the lactic acid of 0.1-1.0 M (or get 100 gram chitosan lactates, and soluble in water), with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 4.0-6.2, add casein 1-100 gram (soluble in water in advance), add TG enzyme 6 grams, in 25 ℃-85 ℃ reactions 1-48 hour, after reaction finishes, with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 6.2-7.0, cross the elimination precipitation, after dialysis or the ultrafiltration desalination, spraying drying or vacuum-drying, get final product the chitosan casein.
Biosynthesizing and the application of embodiment 6 chitosan gsh
Get chitosan 100 gram, be dissolved in the citric acid of 0.1-1.0 M (or get 100 gram Chitosan citrates, and soluble in water), with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 4.0-6.2, add gsh 0.1-20 gram (soluble in water in advance), add TG enzyme 12 grams, in 25 ℃-85 ℃ reactions 1-48 hour, after reaction finishes, with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 6.2-7.0, cross the elimination precipitation, after dialysis or the ultrafiltration desalination, spraying drying or vacuum-drying, get final product the chitosan gsh.
Biosynthesizing and the application of embodiment 7 chitosan ovalbumins
Get chitosan 100 gram, be dissolved in the hydrochloric acid of 0.1-1.0 M (or get 100 gram chitosan hydrochlorides, and soluble in water), with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 4.0-6.2, add ovalbumin 1-100 gram (soluble in water in advance), add TG enzyme 5 grams, in 25 ℃-85 ℃ reactions 1-48 hour, after reaction finishes, with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 6.2-7.0, cross the elimination precipitation, after dialysis or the ultrafiltration desalination, spraying drying or vacuum-drying, get final product the chitosan ovalbumin.
Biosynthesizing and the application of embodiment 8 chitosan silk fibroins
Get chitosan 100 gram, be dissolved in the hydrochloric acid of 0.1-1.0 M (or get 100 gram chitosan hydrochlorides, and soluble in water), with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 4.0-6.2, add silk fibroin 1-100 gram (soluble in water in advance), add TG enzyme 5 grams, in 25 ℃-85 ℃ reactions 1-48 hour, after reaction finishes, with the NaOH of 0.1N or the NaHCO of 0.1N
3Transfer the pH value of solution to 6.2-7.0, cross the elimination precipitation, after dialysis or the ultrafiltration desalination, spraying drying or vacuum-drying, get final product the chitosan silk fibroin.
The performance comparison test of embodiment 9 modified chitosan
Get embodiment 1 gained modified chitosan (chitosan glutin), its bacteriostasis rate, viscosity and pH are tested greater than 6.2 o'clock indexs such as solubleness, namely the chitosan performance before and after the correctability is compared as follows table:
| Performance index | Before the modification | After the modification |
| To intestinal bacteria inhibiting rate (1mg/ml) | 99.8% | 99.6% |
| To streptococcus aureus inhibiting rate (1mg/ml) | 100% | 100% |
| To aspergillus niger inhibiting rate (1mg/ml) | 86% | 84.5% |
| Viscosity (20mg/ml, 37 ℃)) | 45-55cP | 10-12cP |
| Solubleness during pH 7.0 | 0-1% | 4-10% |
Claims (6)
1. the production method of a modified chitosan, it is characterized in that comprising the following step: (1) is got chitosan and is dissolved in organic acid or the inorganic acid solution, regulate pH4.0-6.2, (2) add acry radical donor, add Transglutaminase EC2.3.2.13 again, 25-85 ℃ of fully reaction, regulate pH6.2-7.0, filter and remove precipitation, desalination, drying; Described chitosan or chitosan inorganic acid salt: acry radical donor: the Transglutaminase EC2.3.2.13 mass ratio is=1:0.01-1:0.1; Described adding acry radical donor utilizes the γ-carboxamide groups of its glutamine residue as acry radical donor for adding protein or polypeptide.
2. the method for claim 1 is characterized in that described mineral acid or organic acid soln are hydrochloric acid, acetic acid, lactic acid or the citric acid of 0.1-1mol/L; Described Transglutaminase EC2.3.2.13 is 2000U/g.
3. the method for claim 1, it is characterized in that regulating pH is 6.2.
4. the method for claim 1 is characterized in that described acry radical donor is one or more the mixture in glutin, soybean protein, casein, collagen protein, silk fibroin, the polypeptide, is preferably glutin; Described polypeptide is preferably gsh.
5. the method for claim 1, it is characterized in that described chitosan: acry radical donor: the Transglutaminase EC2.3.2.13 mass ratio is 1:0.2:0.1.
6. the method for claim 1 is characterized in that described desalination takes dialysis or ultrafiltration desalination; Described drying is spraying drying or vacuum-drying.
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| CN103980500A (en) * | 2014-04-23 | 2014-08-13 | 湖南尔康北山明胶有限公司 | Protein-grafted natural polysaccharide, preparation method and application thereof |
| CN104437413A (en) * | 2014-12-26 | 2015-03-25 | 厦门大学 | Method of preparing bio-adsorbent |
| CN104492392A (en) * | 2014-12-26 | 2015-04-08 | 厦门大学 | Application of biological adsorbing agent |
| CN105084498A (en) * | 2015-07-14 | 2015-11-25 | 湖南科技大学 | Preparation method and application for chitosan modified collagen-iron-manganese oxide |
| CN105174406A (en) * | 2015-08-04 | 2015-12-23 | 湖南科技大学 | Preparation method of chitosan modified collagen-iron manganese oxide under ultraviolet irradiation condition and application |
| CN105854839A (en) * | 2016-04-15 | 2016-08-17 | 武汉轻工大学 | Enzymatic crosslinking chitosan/polyethyleneimine grafted magnetic gelatin material and preparing method and application thereof |
| CN106006906A (en) * | 2016-07-02 | 2016-10-12 | 杨奇 | Biodegradable flocculating agent |
| CN106132978A (en) * | 2014-02-19 | 2016-11-16 | 波兰科学院生物化学与生物物理研究所 | A kind of synthetic method of biopolymer derivant, this biopolymer derivant and application thereof |
| CN107376872A (en) * | 2017-08-06 | 2017-11-24 | 桂林理工大学 | Preparation method for the chitosan soybean protein composite porous microspheres of lead absorption |
| CN107372811A (en) * | 2017-07-28 | 2017-11-24 | 平南县正达农业发展有限公司 | A kind of preservation method of pomegranate |
| CN107593872A (en) * | 2017-10-30 | 2018-01-19 | 广东集菜送食品科技有限公司 | Safety and environmental protection meat product Cold Chain Logistics preservation method |
| CN109007411A (en) * | 2018-07-25 | 2018-12-18 | 石阡县毅峰农牧开发有限公司 | One breeder high-protein feed and its processing method |
| CN109517866A (en) * | 2018-11-01 | 2019-03-26 | 天津科技大学 | A method of ferritin-chitosan complexes are prepared using transglutaminase and chitosan |
| CN112537981A (en) * | 2020-12-08 | 2021-03-23 | 中诚国联（河南）生物科技有限公司 | Preparation method and application of composite biological control microbial agent |
| CN112645418A (en) * | 2020-12-01 | 2021-04-13 | 安徽鸿昌糖业科技有限公司 | Composite flocculant for purifying stevioside |
| CN112890187A (en) * | 2021-02-23 | 2021-06-04 | 安徽家佳食品有限责任公司 | Method for preparing convenient nutritional bean shreds |
| CN111393520B (en) * | 2020-03-24 | 2022-07-22 | 江南大学 | Functional material prepared based on milk protein concentrate |
| CN117122058A (en) * | 2023-07-17 | 2023-11-28 | 扬州大学 | Preparation method of curcumin-loaded enzymatic glycosylation modified protein emulsion gel |
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| CN117122058A (en) * | 2023-07-17 | 2023-11-28 | 扬州大学 | Preparation method of curcumin-loaded enzymatic glycosylation modified protein emulsion gel |
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