CN107337706A - A kind of preparation method and application of the antifreeze glycopeptide sugar-modified based on soy oligosaccharides - Google Patents
A kind of preparation method and application of the antifreeze glycopeptide sugar-modified based on soy oligosaccharides Download PDFInfo
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- CN107337706A CN107337706A CN201710483487.7A CN201710483487A CN107337706A CN 107337706 A CN107337706 A CN 107337706A CN 201710483487 A CN201710483487 A CN 201710483487A CN 107337706 A CN107337706 A CN 107337706A
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- Prior art keywords
- antifreeze
- glycopeptide
- preparation
- antifreeze glycopeptide
- sugar
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
- C07K1/1077—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N1/00—Preservation of bodies of humans or animals, or parts thereof
- A01N1/02—Preservation of living parts
- A01N1/0205—Chemical aspects
- A01N1/021—Preservation or perfusion media, liquids, solids or gases used in the preservation of cells, tissue, organs or bodily fluids
- A01N1/0221—Freeze-process protecting agents, i.e. substances protecting cells from effects of the physical process, e.g. cryoprotectants, osmolarity regulators like oncotic agents
Abstract
The invention discloses a kind of preparation method and application of the antifreeze glycopeptide sugar-modified based on soy oligosaccharides, belongs to biology, food processing technology field.Soyabean oligosaccharides sugar chain is incorporated into the antifreeze peptide of separate sources by glycosylation grafting means, synthesizes antifreeze glycopeptide.Antifreeze glycopeptide of the present invention has good antifreezing function, and the cryogenic freezing available for cell, tissue, organ, microorganism and frozen food preserves.Cell, tissue, organ, the freeze survival rate of microorganism for adding antifreeze glycopeptide of the present invention are significantly increased；Apply the invention in freezing food, the stability of the original quality of frozen food can be kept well, significantly reduce food quality deterioration caused by freezing injury.
Description
Technical field
Present invention relates particularly to a kind of preparation method and application of the antifreeze glycopeptide sugar-modified based on soy oligosaccharides, belong to raw
Thing, food processing technology field.
Background technology
Antifreeze protein, be commonly called as ice structural protein, be called and make thermal hysteresis protein, first in 1969 by Devries in the South Pole
A kind of polar region fish in straits（Trematomus borchgrevinki）Blood in find.Antifreeze protein has low-temperature protection work
Property, cryoprotector can be used as to be applied to the neck such as medical science, biology and food processing.As antifreeze protein is applied to tissue, cell
And the Cord blood of microorganism, its freeze survival rate can be significantly improved；Antifreeze protein can reduce frozen food in low temperature cold storage
Ice crystal and its recrystallization quality deterioration to caused by food that process is formed, improve the stability of frozen food.
The Activity of Antifreeze of antifreeze protein is mainly derived from some active fragments in antifreeze protein, is not that whole albumen exists
Work.Few rue of Wang et al. is digested from the collagen of the separate sources such as ox-hide, pigskin and fish-skin by zymolysis technique, separated
Go out the polypeptide fragment with high anti-freezing activity.
In recent years studies have found that recrystallization inhibition activity is served to pass for antifreeze protein performance cryoprotection effect
Important effect, but the heat stagnation of antifreeze protein activity and ice binding characteristic when storage temperature for being less than heat stagnation active temperature area
Between biomaterial（Such as cell, blood, tissue）Destruction even lethal effect is played on the contrary, is primarily due to when storage temperature is less than
During heat stagnation active temperature range, ice-crystal growth is uncontrolled and is quickly converted to acicular texture, and then causes cellular damage to be conciliate
The decline of cell survival rate after jelly.This is also to hinder natural antifreeze protein（Or peptide）Practical application is carried out as cryoprotector
Principal element.Therefore, international research in recent years starts to be directed to develop some, and there is recrystallization inhibition activity to be lived without heat stagnation
The novel antifreeze proteins of property, are exactly one kind of this kind of active material based on glycosylation modified antifreeze protein.Such as one by 4
The peptide chain that Ser-Gly-Gly tripeptides repeats connects what a galactoside base was formed for skeleton and by the carbon teminal of Ser residues
Antifreeze peptide is found that with very strong recrystallization inhibition activity without heat stagnation activity.In addition, research it has also been found that glycosyl species and
Glycosylation position and amino acid residue type have significant impact effect, such as gala to recrystallization inhibitory activity in peptide backbone
Glycosyl modified antifreeze peptide recrystallization inhibition activity is stronger than the antifreeze peptide that mannose group is modified, and proline is conditional due to having
The anglec of rotation can make albumen have obvious secondary structure in the solution, therefore some have stronger recrystallization inhibition containing proline
Activity.
Soyabean oligosaccharides are a kind of low sugariness, sweetener low in calories, and its sugariness is the 70% of sucrose, and its heat is every gram
8.36 kJ (kilojoule)s, only it is the 1/2 of sucrose heat energy, and it is safe and non-toxic.Soyabean oligosaccharides are mainly distributed in soybean plumular axis, and it is led
Composition is wanted as stachyose, gossypose.The insulation of soyabean oligosaccharides, hygroscopicity are smaller than sucrose, but are better than fructose syrup.Soy oligosaccharides
Sugar has the clean intestines of defaecation, promotes Bifidobacterium propagation in enteron aisle, reduce serum cholesterol, protection liver, suppress enteral putrefaction
The effect of the generation of matter.Suitable for person in middle and old age's constipation patient, the irregular people of life, poverty of movement people etc..
Therefore, the present invention closes the antifreeze peptide of separate sources with soyabean oligosaccharides by glycosylation modified means, chemistry
Into antifreeze glycopeptide.The Activity of Antifreeze of synthesized antifreeze glycopeptide is significantly higher than original antifreeze peptide, can be widely applied to cell,
Tissue, organ, the cryogenic freezing of microorganism and frozen food preserve；, can extensive work and this method is safe, easily controllable
Industry metaplasia is produced.
The content of the invention
Present invention aims in view of the shortcomings of the prior art, there is provided a kind of antifreeze glycopeptide sugar-modified based on soy oligosaccharides
Preparation method and application.Cell, tissue, organ, the freeze survival rate of microorganism for adding antifreeze glycopeptide of the present invention are notable
Improve；Apply the invention in freezing food, the stability of the original quality of frozen food can be kept well, significantly
Reduce food quality deterioration caused by freezing injury.
To achieve the above object, the present invention adopts the following technical scheme that：
A kind of preparation method of the antifreeze glycopeptide sugar-modified based on soy oligosaccharides, is prepared as follows：
According to mass ratio it is 1 by antifreeze peptide and soyabean oligosaccharides:1 ~ 1:5 ratio is dissolved in disodium hydrogen phosphate-di(2-ethylhexyl)phosphate
In hydrogen sodium buffer solution, solution ultimate density is 5 ~ 15%（w/v）, stirring makes it fully dissolve；Then in 60 ~ 80 DEG C, pH
To react 1 ~ 2 h under the conditions of 8.0 ~ 9.0；After reaction terminates, it is immediately placed in 0 DEG C of water and cools down with terminating reaction, reaction
Solution freeze-drying afterwards, obtains the sugar-modified antifreeze glycopeptide freeze-dried powder of described soy oligosaccharides.
The raw material sources of described antifreeze peptide powder are in pigskin, ox-hide, fish-skin or fish scale.
The pH of described disodium hydrogen phosphate-phosphate sodium dihydrogen buffer solution is 7.6 ~ 8.0, wherein NaH2PO4For 0.2 M,
Na2HPO4For 0.2 M.
Described mixing time is 10 ~ 20 min；Described cool time is 15 ~ 30 min.
The purposes of antifreeze glycopeptide, described antifreeze glycopeptide are prepared for cell, group made from preparation method as described above
Knit, organ, the cryogenic freezing of microorganism and frozen food preserve.
Technical scheme provided by the present invention has following advantage：
（1）Antifreeze peptide raw material sources used in the present invention have safe and non-toxic, wide material sources, price in food source leftover bits and pieces
The advantage such as cheap；
（2）Antifreeze glycopeptide synthetic method provided by the invention efficiently, safety, cost it is low, it is easily controllable；
（3）The antifreeze glycopeptide that the present invention synthesizes is widely used, and can be applied to cell, tissue, organ, microorganism and frozen food
Cryogenic freezing preserves；And compared with antifreeze peptide, its Activity of Antifreeze significantly improves；
（4）Soyabean oligosaccharides in the present invention are a kind of food with specific function nutrition and specific function, soyabean oligosaccharides
With the clean intestines of defaecation, promote Bifidobacterium propagation in enteron aisle, reduction serum cholesterol, protection liver, suppression enteral corrupt substance
Generation effect.
Specific implementation measure
Below in conjunction with specific embodiment, the present invention will be further described, but the present invention is not limited only to these embodiments.
Embodiment 1
A kind of preparation method of the antifreeze glycopeptide sugar-modified based on soy oligosaccharides, is carried out as follows：
（1）According to antifreeze peptide powder（From pigskin）Mass ratio is 1 between soyabean oligosaccharides:2.7 ratio will be freeze proof more
Gly-His-Lys and soyabean oligosaccharides mixing, it is then dissolved in pH 7.6 disodium hydrogen phosphate-phosphate sodium dihydrogen buffer solution（0.2 M
NaH2PO4, 0.2 M Na2HPO4）In, solution ultimate density is 10%（w/v）, stirring 15 min makes it fully dissolve；
（2）Antifreeze peptide after dissolving reacts 67 min with soyabean oligosaccharides mixed liquor under the conditions of 77 DEG C, pH is 8.74；Instead
After should terminating, it is immediately placed in frozen water and cools down 20 min, terminating reaction, reacted solution freeze-drying, obtains antifreeze glycopeptide
Freeze-dried powder.
Embodiment 2
（1）According to antifreeze peptide powder（From ox-hide）Mass ratio is 1 between soyabean oligosaccharides:1 ratio is by antifreeze peptide
Powder and soyabean oligosaccharides mixing, it is then dissolved in pH 7.0 disodium hydrogen phosphate-phosphate sodium dihydrogen buffer solution（0.2 M
NaH2PO4, 0.2 M Na2HPO4）In, solution ultimate density is 5%（w/v）, stirring 10 min makes it fully dissolve；
（2）Antifreeze peptide after dissolving reacts 67 min with soyabean oligosaccharides mixed liquor under the conditions of 60 DEG C, pH is 8.0；Reaction
After end, it is immediately placed in frozen water and cools down 15 min, terminating reaction, reacted solution freeze-drying, obtains antifreeze glycopeptide jelly
Dry powder.
Embodiment 3
（1）According to antifreeze peptide powder（From fish-skin）Mass ratio is 1 between soyabean oligosaccharides:5 ratio is by antifreeze peptide
Powder and soyabean oligosaccharides mixing, it is then dissolved in pH 8.0 disodium hydrogen phosphate-phosphate sodium dihydrogen buffer solution（0.2 M
NaH2PO4, 0.2 M Na2HPO4）In, solution ultimate density is 15%（w/v）, stirring 20 min makes it fully dissolve；
（2）Antifreeze peptide after dissolving reacts 67 min with soyabean oligosaccharides mixed liquor under the conditions of 80 DEG C, pH is 9.0；Reaction
After end, it is immediately placed in frozen water and cools down 30 min, terminating reaction, reacted solution freeze-drying, obtains antifreeze glycopeptide jelly
Dry powder.
Application of 1 antifreeze glycopeptide of the present invention of application examples in microorganism freezen protective
Carry out as follows：
Test process：A. blank control（Deionized water）, B. soyabean oligosaccharides, C. do not carry out glycosylation modified antifreeze peptide,
D. the antifreeze glycopeptide that prepared by embodiment 1.
Test method：
（1）Prepare seed liquor：The streptococcus thermophilus deposited of going bail for is recovered in M17 fluid nutrient mediums, 37 DEG C, 180 r/min cultures
One night, OD values are about 1.3.
（2）Preparing experiment bacterium solution：50 μ L seed liquor is taken to cultivate 4 in the test tube for filling 4 mL M17 fluid nutrient mediums
H, now the OD of bacterium solution is about 1.2.
（3）Experiment bacterium solution is diluted 100 times with sterile deionized water, takes 100 μ L dilution bacterium solution to be transferred to 2 mL modeling
Expect in cryovial, mixed with 900 μ L freezeproof protectant, turbine mixer mixes.
（4）Take the μ L of sample mixed liquor 50 to cultivate 7 h in 4 mL M17 fluid nutrient mediums, detect the OD at 600 nm
Value.After sample after taking is put into -24 DEG C of h of freezing processing 24,37 DEG C of water-baths 10 min of defrosting, 50 μ L are taken to be inoculated with again
The h of culture assay 7 OD values.
OD values and the relative amount of lactic acid bacteria under the conditions of this meet following relational expression：
y = 0.2152Ln(x)+0.0594, R2 = 0.9972 (2 - 1)
Y is the relative amount of viable bacteria in sample in formula, and x is the OD values that 7 h cultivate bacterium solution.Calculate before and after freezing bacterium in sample
Relative amount C0After C, the survival rate formula of bacterium（2-2）Calculate：
(2 - 2)
C0, before freezing in sample bacterium relative amount（%）；C, after freezing 24 hours in sample bacterium relative amount（%）.Calculate cold
Freeze the bacterium survival rate of processing sample, to detect the Activity of Antifreeze of additive.
1 is the results are shown in Table, soyabean oligosaccharides（Handle B）And antifreeze peptide（Handle C）There is certain resist to streptococcus thermophilus
Freeze protecting effect, the present invention is based on the sugar-modified antifreeze glycopeptide trim of soy oligosaccharides（Handle D）Freeze survival rate be up to
91.8%, it is significantly higher than single soyabean oligosaccharides（49.5%）And antifreeze peptide（66.5%）.Illustrate prepared according to the methods of the invention
Antifreeze glycopeptide there is good antifreezing function, there is good low-temperature protection to act on to the freezing of microorganism.
1 antifreeze glycopeptide of the present invention of table is to microorganism cryoprotection comparative test result
Application of 2 antifreeze glycopeptide of the present invention of application examples in porcine oocytes freezen protective
Porcine oocytes cryoprotector basic recipe, contain in every 100 parts：3 parts of glucose, 1 part of sodium citrate, penicillin 80,000
Unit.
Test process：On porcine oocytes cryoprotector basic recipe in embodiment 4, deionization is added respectively
Antifreeze glycopeptide prepared by water, soyabean oligosaccharides, antifreeze peptide, embodiment 1, protective agent A, B, C, D are accordingly named as by it, to protect
It is control group to protect agent A.
Test method：
（1）Tubulature：Egg mother cell is obtained from discarded pig ovary, is cleaned, moves into the cryopreservation tube equipped with cryoprotector and puts down
Weigh 15 min.
（2）Freeze：The cryopreservation tube that egg mother cell is housed after balance is put into frozen cooling box（2 DEG C of rate of temperature fall/
min）, it is put into liquid nitrogen container and preserves after being cooled to -80 DEG C.
（3）As a result identify：Cultivated after defrosting, calculate survival rate, the results are shown in Table 2.
2 antifreeze glycopeptide of the present invention of table is to egg mother cell cryoprotection comparative test result
From table 2 it can be seen that antifreeze glycopeptide prepared by this method has good antifreezing function, the ultralow temperature of egg mother cell is protected
Tibetan has good protective effect.
Application of 3 antifreeze glycopeptide of the present invention of application examples in potato dough products are freezed
Raw material and formula used in a kind of freezing potato dough of low temperature resistant refrigeration is as follows：100 parts of Plain flour, fresh potato
120 parts, 2 parts of high activity dried yeast, embodiment 1 prepare 4 parts of antifreeze glycopeptide, 80 parts of distilled water.
Test method：
(1) prepared by mashed potatoes：Fresh potato is cleaned and drained, the potato drained is weighed in proportion, is put into high-temperature steam cooker and steams
30 min are boiled, is removed the peel, is put into tissue mashing machine and is pounded mashed potatoes, it is standby to be cooled to room temperature；
(2) activated yeast：Dried yeast powder needed for weighing activates 20 min in 37 DEG C of distilled water；
(3) dough preparing：Antifreeze glycopeptide prepared by embodiment 1 is added in required ratio molten in the yeast juice after activation process
Solution, then mashed potatoes and flour are together poured into dough mixing machine and are sufficiently stirred, knead dough smooth tack-free to dough surface；
(4) split：The dough mixed is divided into dough semifinished product of the dosage for 20 g or so；
(5) shaping：Dough semifinished product is rubbed with the hands circle to be wrapped up with preservative film；
(6) it is quick-frozen：The dough semifinished product wrapped is placed in quick-frozen 60 min of -80 DEG C of refrigerators；
(7) cold storage：Dough base after will be quick-frozen is placed in cold storage in -20 DEG C of refrigerators；
(8) thaw：Freezing flour-dough is placed in temperature as 35 DEG C, relative humidity is 30 min that thawed in 85 % insulating box；
(9) one time fermentation：The dough to have thawed is placed in temperature as 37 DEG C, and relative humidity is the 100min that fermented in 85% insulating box；
(10) knead dough：The good dough of one time fermentation is pressed 10 times with oodle maker；
(11) shaping：The face pressed is made into required steamed bun shape；
(12) secondary fermentation：Dough after whole good type is placed in temperature as 37 DEG C, and relative humidity is to be proofed in 85% insulating box
30min；
(13) steam：The steamed bun semifinished product fermented is placed in the min of big fire boiling 30 in food steamer；Wait taking-up of boiling after 5 min.
Add antifreeze glycopeptide of the present invention freezing flour-dough make steamed bun needed for proofing period it is short, steam obtained by steamed bun specific volume
Greatly, steamed bun center portion is in spongy that delicate mouthfeel is flexible, close with the steamed bread quality made of fresh dough.
Application of 4 antifreeze glycopeptide of the present invention of application examples in frozen minced fish product
Raw material and formula used in a kind of frozen minced fish product of low temperature resistant refrigeration is as follows：60 parts of fish slurry, soybean protein isolate, reality
Apply 5 parts of antifreeze glycopeptide, 30 parts of gelatin, 20 parts of pig ridge fat, 8 parts of starch, 0.4 part of garlic, 1.5 parts of taste beautiful jade, the white sugar 3 of the preparation of example 1
Part, 3 parts of edible salt, 0.3 part of monosodium glutamate, surplus is frozen water.
Test method：
（1）Thaw：By fish slurry thaw to can chopped, but still there is the semi thawing state that part trash ice is advisable in centre；
（2）Cut and mix：By the fish slurry after defrosting and pig ridge fat, garlic, taste beautiful jade, white sugar, edible salt, monosodium glutamate and frozen water in cutmixer
Cut and mix, during which treat that material temperature reaches more than 15 DEG C and adds starch, continue to cut and mix, pulp temperature is 20 DEG C；
（3）After soybean protein isolate is broken into emulsion form, the antifreeze glycopeptide prepared with embodiment 1 is together added in cutmixer, in
Speed, which is cut, mixes uniformly；
（4）Shaping：The mould that the shaping uses, including support, the support are provided with minced fillet feed screw structure, expect
The top and the bottom thermal bonding roller of the pusher plate of rotation, pressure roller and thermal bonding device is equipped with above conduit, the guide portion is set
In the side of framework, minced fillet will be pressed into by sheet by roller machine, then minced fillet piece is rolled into oriental cherry shape by trussing machine.
（5）Boiling：First low temperature boiling：Raw fish ball product after shaping is sent into low temperature water-boiling machine and carries out low temperature boiling,
Boiling temperature is 40 DEG C, and the boiling time is 15 min；Then high temperature boiling：Fish ball product after low temperature boiling is sent into high temperature
High temperature boiling is carried out in water-boiling machine, boiling temperature is 95 DEG C, and the boiling time is 4 min；Finally by the fish ball after high temperature boiling
Product, which is sent into thermophilic digestion machine, carries out thermophilic digestion, and boiling temperature is 121 DEG C, and digestion time is 15 min.
（6）Cooling：The technique of the cooling is as follows：Fish ball product after thermophilic digestion is sent on cooler, makes fish ball
The temperature of product is reduced to room temperature.
（7）It is quick-frozen：The quick-frozen technique is as follows：Fish ball product after cooling is sent into instant freezer, quick-frozen hangar temperature
Less than -30 DEG C, fish ball article center temperature is less than -18 DEG C after the completion of freezing.
（8）Packaging：To examining qualified product to pack, packaged product passes through the detection product of metal detector
In whether be mixed with metallics；
（9）Storage：Qualified product of casing is placed on to less than -18 DEG C of freezer to refrigerate.
Antifreeze glycopeptide of the present invention is added in frozen minced fish product can effectively suppress because the quality that cold storage triggers slightly becomes, coagulated
The problems such as colloidality can be reduced, had a poor flavour；Antifreeze glycopeptide can improve meat products quality, while make surimi product nutrition more rich,
It is more popular with consumers.
It the foregoing is only the preferable embodiment of the present invention, all equivalent changes done according to scope of the present invention patent
With modification, it should all belong to covering scope of the invention.
Claims (5)
- A kind of 1. preparation method of the antifreeze glycopeptide sugar-modified based on soy oligosaccharides, it is characterised in that：It is prepared as follows： According to mass ratio it is 1 by antifreeze peptide and soyabean oligosaccharides:1 ~ 1:5 ratio is dissolved in disodium hydrogen phosphate-sodium dihydrogen phosphate In buffer solution, solution ultimate density is 5 ~ 15%（w/v）, stirring makes it fully dissolve；Then in 60 ~ 80 DEG C, pH 8.0 1 ~ 2 h is reacted under the conditions of ~ 9.0；After reaction terminates, it is reacted molten with terminating reaction to be immediately placed at cooling in 0 DEG C of water Liquid is freeze-dried, and obtains the sugar-modified antifreeze glycopeptide freeze-dried powder of described soy oligosaccharides.
- 2. the preparation method of antifreeze glycopeptide according to claim 1, it is characterised in that：The raw material of described antifreeze peptide powder From pigskin, ox-hide, fish-skin or fish scale.
- 3. the preparation method of antifreeze glycopeptide according to claim 1, it is characterised in that：Described disodium hydrogen phosphate-phosphoric acid The pH of sodium dihydrogen buffer solution is 7.6 ~ 8.0, wherein NaH2PO4For 0.2 M, Na2HPO4For 0.2 M.
- 4. the preparation method of antifreeze glycopeptide according to claim 1, it is characterised in that：Described mixing time be 10 ~ 20 min；Described cool time is 15 ~ 30 min.
- 5. the purposes of antifreeze glycopeptide made from any described preparation method of claim 1 ~ 4, it is characterised in that：Described Antifreeze glycopeptide prepares the cryogenic freezing preservation for cell, tissue, organ, microorganism and frozen food.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103524610A (en) * | 2013-09-25 | 2014-01-22 | 福州大学 | Anti-freezing polypeptide and preparation method thereof |
| CN103805668A (en) * | 2014-03-05 | 2014-05-21 | 山东瀚龙生物科技有限公司 | Sugar modification-based fish skin anti-freeze protein polypeptide and preparation method thereof |
| CN103820516A (en) * | 2014-03-05 | 2014-05-28 | 台州天和水产食品有限公司 | Fishskin protein polypeptide compound with function of freezing resistance based on chitosan oligosaccharide modification |
-
2017
- 2017-06-23 CN CN201710483487.7A patent/CN107337706A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103524610A (en) * | 2013-09-25 | 2014-01-22 | 福州大学 | Anti-freezing polypeptide and preparation method thereof |
| CN103805668A (en) * | 2014-03-05 | 2014-05-21 | 山东瀚龙生物科技有限公司 | Sugar modification-based fish skin anti-freeze protein polypeptide and preparation method thereof |
| CN103820516A (en) * | 2014-03-05 | 2014-05-28 | 台州天和水产食品有限公司 | Fishskin protein polypeptide compound with function of freezing resistance based on chitosan oligosaccharide modification |
Non-Patent Citations (1)
| Title |
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| 陈旭 等: "抗冻多肽-葡聚糖衍生物的制备、优化及活性分析", 《中国食品科学技术年会第十三届年会论文摘要集》 * |
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Application publication date: 20171110 |