CN1803849A - Method for preparing complete water soluble low molecular weight chitosan/chitooligosaccharace - Google Patents
Method for preparing complete water soluble low molecular weight chitosan/chitooligosaccharace Download PDFInfo
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Abstract
The disclosed preparation method for chitose/chitosan oligosaccharide with low molecular weight as 0.18-15mega and well water-solubility comprises: preparing water-soluble chitosan by acetylization; degrading the product with non-specific hydrolase while controlling the enzyme dosage and reaction time; adjusting the degraded product pH value to 8-9 with KOH or NaOH solution; depositing with ethanol, cleaning, and vacuum drying the final product with free amidogen that can promote wound healing, restrains tumor cell growth and improves human immunity. Compared with prior art, this invention is convenient to control for wide application.
Description
Technical field
The present invention relates to a kind of preparation method of simple water-soluble fully low-molecular weight chitoglycan/oligochitosan, belong to renewable resource chemicobiology field.
Background technology
Water-soluble chitosan is the product of chitosan through control deacetylation 40-60% after the acetylize.The water-soluble chitosan of any molecular weight can be water-soluble when lower concentration, and low molecular weight water-soluble shitosan and oligochitosan can be also water-soluble when higher concentration, and have than the better biocompatibility of macromolecule water-soluble chitosan.The water-soluble chitosan of different molecular weight has different bio-physiological activities, so be applied to aspects such as food, medicine for it significant for the water-soluble chitosan of preparation different molecular weight.The method that prepare at present low molecular weight water-soluble shitosan/oligochitosan mainly is first chitosan to be degraded to different molecular weight with chemical method, and then carries out acetylize and improve further that it is water-soluble.This reaction process is loaded down with trivial details, is not easy control.Especially the chemical method degradation process is violent, is not easy to obtain low-molecular weight chitoglycan/oligochitosan, and product structure is modified.
Summary of the invention
At above-mentioned problems of the prior art, the invention provides the method for the water-soluble fully low-molecular weight chitoglycan/oligochitosan of a kind of simple preparation, this method is the reaction process simple controllable not only, and can realize suitability for industrialized production.
Technical scheme provided by the invention is to adopt following steps to prepare this water-soluble low-molecular weight chitoglycan/oligochitosan fully:
(1) chitosan is dissolved in 1%-10% (v/v) acetum, make the chitosan-acetic acid solution that concentration is 0.025-0.040g/ml, ethanol solution with acetic anhydride under magnetic agitation slowly joins in the above-mentioned chitosan solution, room temperature continuously stirring reaction 1-5 hour, obtain water-soluble chitosan solution, wherein the mol ratio of acetic anhydride and chitosan is 5: 2～5: 4, and the volume ratio of dehydrated alcohol and acetum is 3: 2～3: 5.
(2) the reaction solvent dehydrated alcohol is removed in the evaporation of gained water-soluble chitosan solution rotating, regulate its pH to 8-9 with 1-5mol/l potassium hydroxide or sodium hydroxide solution then, water dialysis 24-72 hour of packing in the dialysis tubing, filter dialyzate and remove insolubles, then with filtrate with Rotary Evaporators concentrate, ethanol sedimentation, washing with alcohol, vacuum-drying obtain the water-soluble chitosan powder.
(3) with gained water-soluble chitosan powder dissolution in 0.5-1.5% (v/v) acetum, making concentration is the water-soluble chitosan solution of 0.025-0.040g/ml, potassium hydroxide or sodium hydroxide with 0.05-1mol/l are adjusted the pH value of solution value to 4.0-5.0, add at the bottom of the enzyme than being the non-specificity lytic enzyme of 0.5-5% (w/w), at 50-60 ℃ of continuous oscillation 0.2-6 hour, the hydrolysate hot water bath is boiled and was dezymotized in 5-10 minute, filtering solution then, potassium hydroxide or sodium hydroxide with 1-5mol/l behind the filtrate vacuum concentration is regulated its pH value to 8-9, again through ethanol sedimentation, washing with alcohol, can the gain freedom complete water-soluble low-molecular weight chitoglycan/oligochitosan of amine-format of vacuum-drying.Wherein, the molecular weight ranges of raw materials used chitosan is 300,000-850,000, and the deacetylation scope is 75-95%; Non-specificity lytic enzyme is cellulase, hemicellulase, amylase or neutral protease.If the deacetylation of intermediate product water-soluble chitosan is controlled at 40-60%, can make weight-average molecular weight at last at the complete water-soluble low-molecular weight chitoglycan/oligochitosan of 180,000～1500 free amino group form.
Preparation method provided by the invention is earlier with the chitosan acetylize; the control deacetylation is 40-60%; obtain water-soluble chitosan; use non-narrow spectrum cellulase, hemicellulase, amylase or the neutral protein enzymatic hydrolysis water-soluble chitosan of catalytic amount then; control enzyme dosage and reaction times, the water-soluble chitosan/oligochitosan of acquisition different molecular weight.This method is improved the water-soluble of chitosan by the control deacetylation earlier, is the enzymolysis substrate with this water-soluble chitosan then, the complete water-soluble chitosan of preparation different molecular weight.Can improve the water-soluble of chitosan by control deacetylation and molecular weight, simplify reaction process, realize the controllability of reaction.With non-narrow spectrum commercial enzyme degradation water soluble chitosan, then can realize suitability for industrialized production, reduce cost, guaranteed quality is stable.
Although chitosan is through acetylization reaction; destroyed the regularity of chitosan molecule chain; improved water-soluble; make the water-soluble chitosan of any molecular weight can be water-soluble when lower concentration; but because intramolecularly and intermolecular interaction, the water-soluble chitosan of macromolecule can not be water-soluble fully when high density.And the present invention has not only improved the water-soluble of chitosan, and reduced the molecular weight of water-soluble chitosan, make water-soluble chitosan both can be dissolved in water fully, can also be dissolved in water and organic solvent (as methyl-sulphoxide, N, dinethylformamide) in the mixing solutions, widened the range of application of chitosan.And low-molecular-weight water-soluble chitosan has the activity that promotes wound healing, suppresses growth of tumour cell and raising body immunity, has wide practical use in agricultural, food, makeup and pharmaceutical industries.
Embodiment
Below by specific embodiment the water-soluble fully low-molecular weight chitoglycan of preparation provided by the invention, the method for oligochitosan are elaborated.
Embodiment 1: with deacetylation 75%, the chitosan of weight-average molecular weight 850,000 is dissolved in 100 milliliter of 10% (v/v) acetum, makes the chitosan-acetic acid solution that concentration is 0.040g/ml.To be that 5: 3 acetic anhydride is dissolved in 80 milliliters of dehydrated alcohols with the chitosan mol ratio.Under magnetic agitation this mixing solutions is slowly added in the above-mentioned chitosan solution, room temperature continuously stirring 5 hours obtains water-soluble chitosan solution.The reaction solvent dehydrated alcohol is removed in the evaporation of water-soluble chitosan solution rotating, transfer pH to 8-9 with the 3mol/l sodium hydroxide solution then, the water dialysis 24 hours of packing in the dialysis tubing, dialysate filter is removed insolubles, filtrate concentrates with Rotary Evaporators, ethanol sedimentation, washing with alcohol, vacuum-drying obtains the water-soluble chitosan powder.Water-soluble chitosan is dissolved in 100 milliliter of 1.5% (v/v) acetum, make the chitosan-acetic acid solution that concentration is 0.035g/ml, sodium hydroxide solution with 0.8mol/l is adjusted pH value of solution value to 4.0, this solution is 60 ℃ of insulations, add 0.02 gram cellulase, continuous oscillation 3 hours, the hydrolysate hot water bath is boiled and was dezymotized in 10 minutes, solution filters, sodium hydroxide with 1mol/l behind the filtrate vacuum concentration is transferred pH8-9, ethanol sedimentation, washing with alcohol, vacuum-drying acquisition weight-average molecular weight are 180,000 the complete water-soluble low-molecular weight chitoglycan of free amino group form.
Embodiment 2: with deacetylation 82%, the chitosan of weight-average molecular weight 600,000 is dissolved in 100 milliliter of 3% (v/v) acetum, makes the chitosan-acetic acid solution that concentration is 0.030g/ml.To be that 5: 4 acetic anhydride is dissolved in 60 milliliters of dehydrated alcohols with the chitosan mol ratio.Under magnetic agitation this mixing solutions is slowly added in the above-mentioned chitosan solution, room temperature continuously stirring 3 hours obtains water-soluble chitosan solution.The reaction solvent dehydrated alcohol is removed in the evaporation of water-soluble chitosan solution rotating, transfer pH to 8-9 with the 2mol/l sodium hydroxide solution then, the water dialysis 48 hours of packing in the dialysis tubing, dialysate filter is removed insolubles, filtrate concentrates with Rotary Evaporators, ethanol sedimentation, washing with alcohol, vacuum-drying obtains the water-soluble chitosan powder.Water-soluble chitosan is dissolved in 100 milliliter of 1.0% (v/v) acetum, making concentration is the water-soluble chitosan acetum of 0.030g/ml, potassium hydroxide solution with 0.10mol/l is adjusted pH value of solution value to 4.5, this solution is 55 ℃ of insulations, add 0.025 gram hemicellulase, continuous oscillation 2 hours, the hydrolysate hot water bath is boiled and was dezymotized in 10 minutes, solution filters, potassium hydroxide with 3mol/l behind the filtrate vacuum concentration is transferred pH8-9, ethanol sedimentation, washing with alcohol, vacuum-drying acquisition weight-average molecular weight are 110,000 the complete water-soluble low-molecular weight chitoglycan of free amino group form.
Embodiment 3: with deacetylation 89%, the chitosan of weight-average molecular weight 440,000 is dissolved in 100 milliliter of 1% (v/v) acetum, makes the chitosan-acetic acid solution that concentration is 0.025g/ml.Under magnetic agitation, will be that 5: 2 acetic anhydride is dissolved in 150 milliliters of dehydrated alcohols with the chitosan mol ratio.This mixing solutions is slowly added in the above-mentioned chitosan solution, and room temperature continuously stirring 1 hour obtains water-soluble chitosan solution.The reaction solvent dehydrated alcohol is removed in the evaporation of water-soluble chitosan solution rotating, transfer pH to 8-9 with the 5mol/l sodium hydroxide solution then, the water dialysis 36 hours of packing in the dialysis tubing, dialysate filter is removed insolubles, filtrate concentrates with Rotary Evaporators, ethanol sedimentation, washing with alcohol, vacuum-drying obtains the water-soluble chitosan powder.Water-soluble chitosan is dissolved in 100 milliliter of 0.5% (v/v) acetum, making concentration is the water-soluble chitosan acetum of 0.025g/ml, potassium hydroxide solution with 0.05mol/l is adjusted pH value of solution value to 4.0, this solution is 50 ℃ of insulations, add 0.1 gram cellulase, continuous oscillation 0.2 hour, the hydrolysate hot water bath is boiled and was dezymotized in 5 minutes, solution filters, potassium hydroxide with 5mol/l behind the filtrate vacuum concentration is transferred pH8-9, ethanol sedimentation, washing with alcohol, vacuum-drying acquisition weight-average molecular weight are 60,000 the complete water-soluble low-molecular weight chitoglycan of free amino group form.
Embodiment 4: with deacetylation 95%, the chitosan of weight-average molecular weight 300,000 is dissolved in 100 milliliter of 8% (v/v) acetum, makes the chitosan-acetic acid solution that concentration is 0.040g/ml.To be that 5: 3 acetic anhydride is dissolved in 100 milliliters of dehydrated alcohols with the chitosan mol ratio.Under magnetic agitation this mixing solutions is slowly added in the above-mentioned chitosan solution, room temperature continuously stirring 3 hours obtains water-soluble chitosan solution.The reaction solvent dehydrated alcohol is removed in the evaporation of water-soluble chitosan solution rotating, transfer pH to 8-9 with the 5mol/l potassium hydroxide solution then, the water dialysis 72 hours of packing in the dialysis tubing, dialysate filter is removed insolubles, filtrate concentrates with Rotary Evaporators, ethanol sedimentation, washing with alcohol, vacuum-drying obtains the water-soluble chitosan powder.Water-soluble chitosan is dissolved in 100 milliliter of 0.5% (v/v) acetum, make the chitosan-acetic acid solution that concentration is 0.040g/ml, potassium hydroxide solution with 0.5mol/l is adjusted pH value of solution value to 4.5, this solution is 55 ℃ of insulations, add 0.16 gram amylase, continuous oscillation 5 hours, the hydrolysate hot water bath is boiled and was dezymotized in 8 minutes, solution filters, potassium hydroxide with 3mol/l behind the filtrate vacuum concentration is transferred pH8-9, ethanol sedimentation, washing with alcohol, vacuum-drying acquisition weight-average molecular weight are 10,000 the complete water-soluble low-molecular weight chitoglycan of free amino group form.
Embodiment 5: with deacetylation 95%, the chitosan of weight-average molecular weight 300,000 is dissolved in 100 milliliter of 5% (v/v) acetum, makes the chitosan-acetic acid solution that concentration is 0.040g/ml.To be that 5: 3 acetic anhydride is dissolved in 100 milliliters of dehydrated alcohols with the chitosan mol ratio.Under magnetic agitation this mixing solutions is slowly added in the above-mentioned chitosan solution, room temperature continuously stirring 5 hours obtains water-soluble chitosan solution.The reaction solvent dehydrated alcohol is removed in the evaporation of water-soluble chitosan solution rotating, transfer pH to 8-9 with the 1mol/l sodium hydroxide solution then, the water dialysis 48 hours of packing in the dialysis tubing, dialysate filter is removed insolubles, filtrate concentrates with Rotary Evaporators, ethanol sedimentation, washing with alcohol, vacuum-drying obtains the water-soluble chitosan powder.Water-soluble chitosan is dissolved in 100 milliliter of 1.5% (v/v) acetum, make the chitosan-acetic acid solution that concentration is 0.040g/ml, sodium hydroxide solution with 1.00mol/l is adjusted pH value of solution value to 5.0, this solution is 60 ℃ of insulations, add 0.2 gram neutral protease, continuous oscillation 6 hours, the hydrolysate hot water bath is boiled and was dezymotized in 10 minutes, solution filters, sodium hydroxide with 3mol/l behind the filtrate vacuum concentration is transferred pH8-9, ethanol sedimentation, washing with alcohol, vacuum-drying acquisition weight-average molecular weight are 1500 the complete water-soluble oligochitosan of free amino group form.
Claims (5)
1, a kind of preparation method of fully water-soluble low-molecular weight chitoglycan/oligochitosan is characterized in that adopting following concrete steps:
(1) chitosan is dissolved in 1%-10% (v/v) acetum, make the chitosan-acetic acid solution that concentration is 0.025-0.040g/ml, ethanol solution with acetic anhydride under magnetic agitation slowly joins in the above-mentioned chitosan solution, room temperature continuously stirring reaction 1-5 hour, obtain water-soluble chitosan solution, wherein the mol ratio of acetic anhydride and chitosan is 5: 2～5: 4, and the volume ratio of dehydrated alcohol and acetum is 3: 2～3: 5.
(2) the reaction solvent dehydrated alcohol is removed in the evaporation of gained water-soluble chitosan solution rotating, regulate its pH to 8-9 with 1-5mol/l potassium hydroxide or sodium hydroxide solution then, water dialysis 24-72 hour of packing in the dialysis tubing, filter dialyzate and remove insolubles, then with filtrate with Rotary Evaporators concentrate, ethanol sedimentation, washing with alcohol, vacuum-drying obtain the water-soluble chitosan powder.
(3) with gained water-soluble chitosan powder dissolution in 0.5-1.5% (v/v) acetum, making concentration is the water-soluble chitosan solution of 0.025-0.040g/ml, potassium hydroxide or sodium hydroxide with 0.05-1mol/l are adjusted the pH value of solution value to 4.0-5.0, add at the bottom of the enzyme than being the non-specificity lytic enzyme of 0.5-5% (w/w), at 50-60 ℃ of continuous oscillation 0.2-6 hour, the hydrolysate hot water bath is boiled and was dezymotized in 5-10 minute, filtering solution then, potassium hydroxide or sodium hydroxide solution with 1-5mol/l behind the filtrate vacuum concentration regulated its pH value to 8-9, again through ethanol sedimentation, washing with alcohol, can the gain freedom complete water-soluble low-molecular weight chitoglycan/oligochitosan of amine-format of vacuum-drying.
2, the preparation method of fully water-soluble low-molecular weight chitoglycan/oligochitosan according to claim 1, it is characterized in that: the deacetylation of intermediate product water-soluble chitosan is controlled at 40-60%, can makes weight-average molecular weight at last at the complete water-soluble low-molecular weight chitoglycan/oligochitosan of 180,000～1500 free amino group form.
3, the preparation method of fully water-soluble low-molecular weight chitoglycan/oligochitosan according to claim 1 and 2, it is characterized in that: the molecular weight ranges of raw materials used chitosan is 300,000-850,000.
4, the preparation method of fully water-soluble low-molecular weight chitoglycan/oligochitosan according to claim 1 and 2, it is characterized in that: the deacetylation scope of raw materials used chitosan is at 75%-95%.
5, the preparation method of fully water-soluble low-molecular weight chitoglycan/oligochitosan according to claim 1 and 2, it is characterized in that: non-specificity lytic enzyme is cellulase, hemicellulase, amylase or neutral protease.
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Assignee: Hubei Provence Qianjiang City Huashan Aquatic Food Co., Ltd. Assignor: Wuhan University Contract fulfillment period: 2009.6.8 to 2014.6.8 contract change Contract record no.: 2009420000050 Denomination of invention: Method for preparing complete water soluble low molecular weight chitosan/chitooligosaccharace Granted publication date: 20080604 License type: Exclusive license Record date: 2009.6.12 |
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Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2009.6.8 TO 2014.6.8; CHANGE OF CONTRACT Name of requester: HUBEI PROVINCE QIANJIANG CITY HUASHAN AQUATIC PROD Effective date: 20090612 |
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Granted publication date: 20080604 Termination date: 20100118 |