CN101906213A - Novel protein glycosylation grafting method - Google Patents
Novel protein glycosylation grafting method Download PDFInfo
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- CN101906213A CN101906213A CN2010102374561A CN201010237456A CN101906213A CN 101906213 A CN101906213 A CN 101906213A CN 2010102374561 A CN2010102374561 A CN 2010102374561A CN 201010237456 A CN201010237456 A CN 201010237456A CN 101906213 A CN101906213 A CN 101906213A
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Abstract
The invention discloses a novel protein glycosylation grafting method. The method comprises the following steps of: (1) adding buffer solution into a crowding reagent and stirring the mixture to obtain solution; and (2) adding protein and glucan into the solution obtained by the step (1), stirring the mixture for 2 hours, adding NaN3 into the mixture, placing the mixture for 24 hours at the temperature of 5 DEG C, stirring the mixture for 12 to 48 hours at the temperature of between 50 and 70 DEG C again and quickly cooling the mixture to the temperature of less than 25 DEG C to obtain a glycosylation protein product. The method has the advantages of greatly improving functional characters such as water solubility, emulsibility, antioxidation and the like of a graft, along with convenient operation and high reaction efficiency; and the product has industrial and large-scale application prospect.
Description
Technical field
The invention belongs to field of food, relate to protein modified method, particularly a kind of method of novel protein glycosylation grafting.
Background technology
Protein and polysaccharide are to coexist as most important two class biomacromolecules in the food emulsification system, are the principal elements that influences food configuration and matter structure.Protein reduces interfacial tension how to serve as emulsifying agent in colloidal dispersion because of can form adsorption layer on liquid liquid or liquid-gas interface, polysaccharide is then used always and is made stablizer owing to its good thickening and water retention characteristic, has given the performance of the function when system is different from both Individual existences thus.The protein of covalent bonds and polysaccharide form grafts, not only keep proteinic surfactivity but also had the hydrophilicity of polysaccharide, mixture contrast with protein polysaccharide weak interaction forms has higher adaptability to envrionment conditions (temperature, pH value, ionic strength etc.).
By spontaneous Maillard reaction proteinic epsilon-amino group is combined with the reductibility carbonyl of polysaccharide is terminal, can obtain having the protein glycosylation grafting thing of superior functionality character.Up to the present, effectively the preparation method still is a dry heating method, and its principle is to be in non-accumulative response behaviour by the amino in the protein under lower water-activity, so so that reactive group and polysaccharide generation covalent attachment to be provided.But dry heating method has long reaction time, the uncontrollable defective that waits self of Maillard level of response.In foodstuffs industry, Food science men often wish that reaction occurs in aqueous phase freely, and take place in traditional aqueous solution also can make the protein molecular sex change and produce protein aggregation when the Maillard reaction generates glycosylated protein.Therefore, for extremely, polysaccharide and proteic Maillard are reflected in the aqueous solution effectively carry out up till now.
" macromole crowded " (macromolecular crowding) is completely new concept in the life science, and scientist advised strongly that factor was the same studies biomacromolecule as conventional factor " macromole is crowded " environment and pH, ionic strength and solution composition etc. in recent years.When having the biomacromolecule of high density in the system, molecular repulsion volume theory (excluded volume effect) is followed in the reaction between the macromole, promotes reaction to the direction that the solute cumulative volume reduces, and promptly moves towards bonding position; In addition, the albumen molecular configuration tends towards stability under the crowded environment of macromole, and protein denaturation degree and aggregation extent will alleviate.Thus, this project proposes polysaccharide and protein are in the crowded environment of macromole as biomacromolecule, albumen can be in non-sex change or few accumulative response behaviour, also will carry out towards forming covalently bound reaction path in the aqueous solution with the Maillard reaction of polysaccharide.The present invention with " macromole crowded " environmental applications in the life science in generating the protein-polysaccharide functional macromolecule, according to the molecular repulsion volume theory under the crowded environment of macromole, albumen and polysaccharide in the aqueous solution will preferentially carry out towards the bonded direction, make in this environment albumen take place to assemble simultaneously or the probability of sex change reduces greatly, and the macromole of conduct " crowded reagent ", can be the inertia superpolymer, also can be to participate in the polysaccharide that reacts simultaneously.
Summary of the invention
The purpose of this invention is to provide a kind of novel protein glycosylation grafting method.The present invention simulates the crowded system of macromole of life science, and the crowded reagent in the system can be inertia superpolymer or dextran.That this method has is easy to operate, reaction times weak point, stable performance, products therefrom do not produce advantages such as brown stain; product has the application prospect of favorable industrialization, mass-producing, and this method has overcome existing protein and sugared grafting method is difficult to realize industrialized defective.
Purpose of the present invention is achieved through the following technical solutions:
A kind of method of novel protein glycosylation grafting may further comprise the steps:
(1) in crowded reagent, adds buffered soln, stir, obtain solution;
(2) albumen and dextran are added in the solution that step (1) obtains, stir 2h after, add NaN
3, place 24h at 5 ℃, again 50～70 ℃ stir 12～48h after, be cooled to rapidly and be lower than 25 ℃, obtain the glycosylated protein product;
The mass fraction of described crowded reagent is 10～40 parts,
Proteic mass fraction is 1～10 part,
The mass ratio of albumen and polysaccharide is 1: 3～1: 6.
Described albumen is the heavy albumen of soy acid, soybean protein isolate, whey-protein, beta-lactoglobulin or wheat-gluten.
Described crowded reagent is polymer inert polymer or polysaccharide.
Described crowded reagent is the polymer inert polymer, for example; Ficol1 70 or PEG2000.
Described crowded reagent is polysaccharide, for example: Dextran 70, Dextran 10 or Dextran 40.
Described buffered soln is the phosphate buffered saline buffer of pH 5.0～8.0
A kind of method of novel protein glycosylation grafting may further comprise the steps:
(1) with albumen and crowded agent dissolves in buffered soln, stir 2h after, add NaN
3,
(2) place 24h at 5 ℃, again 50～70 ℃ stir 12～48h after, be cooled to rapidly and be lower than 25 ℃, obtain the glycosylated protein product;
The mass ratio of albumen and crowded reagent is 1: 3～1: 6.
Described albumen is the heavy albumen of soy acid, soybean protein isolate, whey-protein, beta-lactoglobulin or wheat-gluten.
Described crowded reagent is polysaccharide.For example: Dextran 70, Dextran 10 or Dextran 40.
Described buffered soln is the phosphate buffered saline buffer of pH 5.0～8.0.
The glycosylated protein product of method preparation of the present invention.
The application of described glycosylated protein product in preparation modified protein or foodstuff additive.
Described glycosylated protein product is purifying or utilize the gel filtration chromatography purifying to remove unreacted albumen and dextran and inertia superpolymer not.
The principle of the invention is as follows:
By spontaneous Maillard reaction proteinic epsilon-amino group is combined with the reductibility carbonyl of polysaccharide is terminal, can obtain having the protein glycosylation covalence graft thing of superior functionality character.Therefore in reaction process, select for use the reactive grafting degree as detecting index.It is the content of free amino group in the o-phthalaldehyde(OPA) method assaying reaction liquid that graft(ing) degree adopts the OPA method, the degree that reflects graft modification, its principle be according to the free amino group in OPA and the protein in the presence of beta-mercaptoethanol, the compound that generates has absorption at the 340nm place, utilize spectrophotometry can calculate free amino group content in the reaction solution in view of the above, with the degree of reactive grafting modification.
The present invention adopts " macromole crowd environment " as the reaction system that generates glycosylated protein, by crowded theory in the life science further is applied to the preparation of protein glycosylation grafting thing to the stable scientific phenomena of protein structure.The crowded environment of macromole can make protein molecular be in non-gathering or less accumulative response behaviour equally in the aqueous solution, simultaneously, promotes the reaction of albumen and polysaccharide to carry out towards covalently bound direction.
The relative prior art of the present invention has following advantage and beneficial effect:
(1) in the present invention, the covalence graft of soybean protein and polysaccharide,, only carry out under the temperature of gentleness in aqueous phase solution as catalyzer without any need for chemical reagent, " macromole crowd environment " of simulation in the life science carries out proteinic glycosylation; Speed of response is very fast, and the product color is creamy white;
(2) can free stirring reaction in the water react, overcome the uneven shortcoming of reaction in the xeothermic reaction, farthest polysaccharide fully contacts with protein;
(3) compare with other graft-modification methods, the present invention has the application prospect of mass-producing, and industry is workable.
Embodiment:
Embodiment 1:
Accurately take by weighing 0.5g soybean protein, 1.5g dextran, be dissolved in the buffer solution of sodium phosphate of 10mL 0.01mol/L pH 6.5, behind the stirring at room 2h, add 3 NaN
3(0.02%w/w) anticorrosion, place 24h at 5 ℃, 60 ℃ of constant temperature, stirring velocity is to stir 30h under the 500r/min condition.Reaction is cooled to the room temperature termination reaction rapidly after finishing, and lyophilize obtains the glycosylated protein product.
Comparative example 1-1:
Accurately take by weighing the 0.5g soybean protein, be dissolved in the buffer solution of sodium phosphate of 10mL 0.01mol/L pH 6.5, behind the stirring at room 2h, add 3 NaN
3(0.02%w/w) anticorrosion, place 24h at 5 ℃, 60 ℃ of constant temperature, stirring velocity is to stir 30h under the 500r/min condition.Reaction is cooled to the room temperature termination reaction rapidly, lyophilize after finishing.
Comparative example 1-2:
Accurately take by weighing 0.01g soybean protein, 0.03g dextran, be dissolved in the buffer solution of sodium phosphate of 10mL 0.01mol/L pH 6.5, behind the stirring at room 2h, add 3 NaN
3(0.02%w/w) anticorrosion, place 24h at 5 ℃, 60 ℃ of constant temperature, stirring velocity is to stir 30h under the 500r/min condition.Reaction is cooled to the room temperature termination reaction rapidly, lyophilize after finishing.
Adopt the o-phthalaldehyde(OPA) method to measure the graft(ing) degree of gained glycosylation soybean protein.The performance comparison result of embodiment 1 and comparative example's 1 binding substances is as shown in table 1:
Table 1
As can be seen from Table 1, in the embodiment of the invention 1 with dextran not only as crowded reagent but also as reaction polysaccharide gained glycosylated protein graft(ing) degree height, colours white, too low among the comparative example 1-2 owing to system reactant concentration, do not make that polysaccharide and albumen are effective to be combined, graft(ing) degree is lower, and reaction effect is not obvious; Association reaction can't take place in thermal treatment (comparative example 1-1) the back explanation protein itself that soybean protein carries out under the similarity condition.
Embodiment 2:
1gPEG2000 is placed reaction unit as crowded reagent, add the buffer solution of sodium phosphate of 10mL 0.01mol/L pH 7.0, stir 2h, make it abundant aquation dissolving, 0.2g soybean protein and 0.6g dextran add in this solution that contains crowded reagent, fully stir 2h after, add NaN
3(0.02%w/w) anticorrosion, behind 5 ℃ of placement 24h, 50 ℃ are stirred 48h, and reaction is cooled to 24 ℃ rapidly after finishing, and obtains the glycosylated protein product, removes unreacted albumen and dextran and inertia superpolymer PEG2000 by the gel filtration chromatography purifying.
Comparative example 2-1:
1g PEG2000 is placed reaction unit as crowded reagent, add the buffer solution of sodium phosphate of 10mL 0.01mol/L pH 7.0, stir 2h, make it abundant aquation dissolving, 0.2g soybean protein adds in this solution that contains crowded reagent, fully stir 2h after, add NaN
3(0.02%w/w) anticorrosion, behind 5 ℃ of placement 24h, 50 ℃ are stirred 48h, and reaction is cooled to 24 ℃ rapidly after finishing, and obtains the glycosylated protein product, removes unreacted albumen and dextran and inertia superpolymer PEG2000 by the gel filtration chromatography purifying.
Comparative example 2-2:
Reaction unit adds the buffer solution of sodium phosphate of 10mL 0.01mol/L pH 7.0, stirs 2h, and 0.2g soybean protein and 0.6g dextran join in this solution, fully stir 2h after, add NaN
3(0.02%w/w) anticorrosion, behind 5 ℃ of placement 24h, 50 ℃ are stirred 48h, and reaction is cooled to 24 ℃ rapidly after finishing, and obtains the glycosylated protein product, removes unreacted albumen and dextran by the gel filtration chromatography purifying.
Table 2
From the performance comparison of table 2 embodiment 2 and comparative example's binding substances as can be seen, the embodiment of the invention 2 is higher for crowded reagent place gets the glycosylated protein graft(ing) degree with PEG2000, colours white, among the comparative example 2-2 owing to do not add the crowded reagent of inertia in the system, do not form the crowded environment of macromole, do not make that polysaccharide and albumen are effective to be combined, graft(ing) degree is lower, and reaction effect is not obvious; Association reaction can't take place in thermal treatment (comparative example 2-1) the back explanation protein itself that soybean protein carries out under the similarity condition.
Embodiment 3:
Accurately take by weighing 0.6g soybean protein, 3.6g dextran, be dissolved in the buffer solution of sodium phosphate of 20mL 0.01mol/L pH 7.5, behind the stirring at room 2h, add 3 NaN
3(0.02%w/w) anticorrosion, place 24h at 5 ℃, 70 ℃ of constant temperature, stirring velocity is to stir 12h under the 500r/min condition.Reaction is cooled to the room temperature termination reaction rapidly, lyophilize after finishing.
Embodiment 4:
1.5gPEG2000 is placed reaction unit as crowded reagent, add the buffer solution of sodium phosphate of 10mL 0.01mol/L pH 6.0, stir 2h, make it abundant aquation dissolving, 0.5g soybean protein and 2.5g dextran add in this solution that contains crowded reagent, fully stir 2h after, add NaN
3(0.02%w/w) anticorrosion, behind 5 ℃ of placement 24h, 60 ℃ are stirred 36h, and reaction is cooled to 20 ℃ rapidly after finishing, and obtains the glycosylated protein product, removes unreacted albumen and dextran and inertia superpolymer PEG2000 by the gel filtration chromatography purifying.
Embodiment 5:
1.5g Ficol170 is placed reaction unit as crowded reagent, add the buffer solution of sodium phosphate of 10mL 0.01mol/L pH 5.5, stir 2h, make it abundant aquation dissolving, 0.5g soybean protein and 3.0g dextran add in this solution that contains crowded reagent, fully stir 2h after, add NaN
3(0.02%w/w) anticorrosion, behind 5 ℃ of placement 24h, 70 ℃ are stirred 12h, and reaction is cooled to 19 ℃ rapidly after finishing, and obtains the glycosylated protein product, removes unreacted albumen and dextran and Ficol170 by the gel filtration chromatography purifying.
Claims (10)
1. the method for a novel protein glycosylation grafting is characterized in that, may further comprise the steps:
(1) in crowded reagent, adds buffered soln, stir, obtain solution;
(2) albumen and dextran are added in the solution that step (1) obtains, stir 2h after, add NaN
3, place 24h at 5 ℃, again 50～70 ℃ stir 12～48h after, be cooled to rapidly and be lower than 25 ℃, obtain the glycosylated protein product;
The mass fraction of described crowded reagent is 10～40 parts,
Proteic mass fraction is 1～10 part,
The mass ratio of albumen and polysaccharide is 1: 3～1: 6.
2. method according to claim 1 is characterized in that, described albumen is the heavy albumen of soy acid, soybean protein isolate, whey-protein, beta-lactoglobulin or wheat-gluten.
3. method according to claim 1 is characterized in that, described crowded reagent is polymer inert polymer or polysaccharide.
4. method according to claim 1 is characterized in that, described buffered soln is the phosphate buffered saline buffer of pH 5.0～8.0.
5. the method for a novel protein glycosylation grafting is characterized in that, may further comprise the steps:
(1) with albumen and crowded agent dissolves in buffered soln, stir 2h after, add NaN
3,
(2) place 24h at 5 ℃, again 50～70 ℃ stir 12～48h after, be cooled to rapidly and be lower than 25 ℃, obtain the glycosylated protein product;
The mass ratio of albumen and crowded reagent is 1: 3～1: 6.
6. method according to claim 5 is characterized in that, described albumen is the heavy albumen of soy acid, soybean protein isolate, whey-protein, beta-lactoglobulin or wheat-gluten.
7. method according to claim 5 is characterized in that, described crowded reagent is polysaccharide.
8. method according to claim 5 is characterized in that, described buffered soln is the phosphate buffered saline buffer of pH 5.0～8.0.
9. glycosylated protein product according to each described method preparation of claim 1～7.
10. the application of the described glycosylated protein product of claim 9 in preparation modified protein or foodstuff additive.
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Cited By (8)
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| CN102308904A (en) * | 2011-07-20 | 2012-01-11 | 华南理工大学 | Method for rapidly preparing glycopeptides |
| CN103445282A (en) * | 2013-07-19 | 2013-12-18 | 华南理工大学 | Preparation method of corn peptide glycosylation product nano particles embedding lipid-soluble vitamins |
| CN106916319A (en) * | 2017-04-01 | 2017-07-04 | 南京中医药大学 | The ginkgo protein preparation method and applications of glucan graft modification |
| CN107151333A (en) * | 2017-05-17 | 2017-09-12 | 朱吴喆 | A kind of glucan graft modification technique of wheat gluten protein |
| CN109105618A (en) * | 2018-06-08 | 2019-01-01 | 河南蜀正园食品有限公司 | Rich in flavones albumen and its preparing the application in health food |
| CN110591102A (en) * | 2019-09-25 | 2019-12-20 | 临沂大学 | Preparation method of peanut protein isolate-glucan graft polymer |
| CN113637063A (en) * | 2021-08-17 | 2021-11-12 | 华南理工大学 | Preparation process of dextran aldehyde glycosylated sodium caseinate |
| CN113651972A (en) * | 2021-09-02 | 2021-11-16 | 浙江工商大学 | Preparation method of graft modified fish protein-sugar coupling compound |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110591102B (en) * | 2019-09-25 | 2021-08-27 | 临沂大学 | Preparation method of peanut protein isolate-glucan graft polymer |
| CN113637063A (en) * | 2021-08-17 | 2021-11-12 | 华南理工大学 | Preparation process of dextran aldehyde glycosylated sodium caseinate |
| CN113651972A (en) * | 2021-09-02 | 2021-11-16 | 浙江工商大学 | Preparation method of graft modified fish protein-sugar coupling compound |
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