CN105670010B - A kind of preparation method of rice protein/forulic acid compound or cross-linking agent - Google Patents
A kind of preparation method of rice protein/forulic acid compound or cross-linking agent Download PDFInfo
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- CN105670010B CN105670010B CN201610014670.8A CN201610014670A CN105670010B CN 105670010 B CN105670010 B CN 105670010B CN 201610014670 A CN201610014670 A CN 201610014670A CN 105670010 B CN105670010 B CN 105670010B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2389/00—Characterised by the use of proteins; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
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Abstract
The preparation method of a kind of rice protein/forulic acid compound or cross-linking agent, comprises the following steps：(1) rice protein/forulic acid/laccase mixed liquor is prepared, in the rice protein/forulic acid/laccase mixed liquor, the mass concentration of rice protein is 8~12mg/mL, and the mass concentration of forulic acid is 0.05~0.4mg/mL, and the mass concentration of laccase is 0~0.1mg/mL.(2) after the agitated fully reaction of rice protein/forulic acid/laccase mixed liquor, the free forulic acid not combined with rice protein is removed by dialysing, then be freeze-dried to obtain rice protein/forulic acid compound or rice protein/ferulic acid crosslinks thing.The achievable continuous production of the present invention, rice protein/ferulic acid crosslinks thing have preferable antioxidation activity in vitro；It may be used on the strong medical treatment of some oxidation resistances, food and field of polymer technology.
Description
Technical field
The invention belongs to corn gluten protein field of deep, specifically a kind of rice protein/forulic acid compound or cross-linking agent
Preparation method.
Background technology
Free radical caused by human metabolism has very strong lethal effect to body tissue cell, and cell can be caused dead
Die and tissue damage, such as atherosclerosis, cancer, injury of lungs and aging.Vegetable protein is as one kind, because it has processing
Characteristic and nutritive peculiarity and as Recent study focus.Rice protein (Rice protein, RP) is a kind of high-quality plant
Thing albumen, there is the advantages that amino acid Compositional balance is reasonable, and mouthfeel is gentle, hypoallergenic and reduction cholesterol；And rice egg
Various amino acid containing needed by human body in white, reasonable mixture ratio, meet the idealized model that WHO/FAO recommends.But with rice egg
Oxidative degradation easily occurs for the rich grease-contained food prepared in vain, polyphenols because it has natural anti-oxidation characteristics,
It is increasing to be applied in rich grease-contained food processing, so as to play antioxidation.The combination of albumen and polyphenol is protected
The functional character of protein is stayed, while imparts the higher anti-oxidation characteristics of protein again, these have higher active product
There are fine market prospects applied to food, cosmetics health care, field of medicaments.
Forulic acid (Ferulic acid, FA) is the common phenolic acid in cereal, there is stronger suppression lipid
The ability and hypotoxicity of oxidative degradation, are widely used in food and medicine trade.Research found under natural conditions, forulic acid and egg
Association reaction can occur for white matter, forulic acid and protein can with non-covalent bond (hydrogen bond, hydrophobic or ion interaction) or
Covalent bond is connected.In addition, the reaction condition of alkalescence or high temperature will promote albumen to be preferably crosslinked with phenolic acid, it may be possible to due to
Forulic acid is easily oxidized to quinone in the basic conditions, and quinone can crosslink reaction with the amino in protein molecule and sulfydryl.
But chemical method has the following disadvantages：Reaction condition may produce toxic intermediates under high temperature and alkalescence condition, food
Poor with property, color is deep, and reaction condition is unstable.In general, enzyme process cross linking conditions are gentleer.
Laccase (Laccase, LAC) is a kind of polyphenol oxidase, can combine multiple copper ions, belong to covellite oxidizing ferment.Paint
For enzyme as biocatalyst, not only with efficient catalytic effect, and the final product of its catalysis is water, therefore is also one
Kind green catalyst.Laccase Catalyzed phenolic acid is effectively improved the functional character and physiologically active (antibacterial work of albumen with protein cross
With, antioxidation activity), phenolic acid may be attributed to and can be reacted after laccase aoxidizes with amino, sulfydryl in protein cause
The crosslinking of protein, cross-linking agent remain phenols active group, and so as to improve the natural attribute of protein, these products can answer
Use the strong medical treatment of some oxidation resistances, food and field of polymer technology.Therefore, select forulic acid and rice protein mutual herein
With reference to improve its functional character while high anti-oxidation activity is obtained, this is to substantially effectively utilizing rice protein resource
Have far-reaching significance.
The content of the invention
The present invention is interacted for existing rice protein with forulic acid and its Antioxidation Mechanism research and imperfection, prepares
Forulic acid/rice protein cross-linking agent with more high anti-oxidation activity, and polyphenol oxidase is added in system, so as to obtain
Feature rice protein dispensing with more high anti-oxidation activity, there is provided a kind of new enzyme process prepares feature rice bran protein
Method.
Technical scheme is as follows：
The preparation method of a kind of rice protein/forulic acid compound or cross-linking agent, comprises the following steps：
(1) rice protein/forulic acid/laccase mixed liquor is prepared, in the rice protein/forulic acid/laccase mixed liquor, greatly
The mass concentration of rice gluten is 8~12mg/mL, and the mass concentration of forulic acid is 0.05~0.4mg/mL, the mass concentration of laccase
For 0~0.1mg/mL,
(2) rice protein/forulic acid/laccase mixed liquor it is agitated fully reaction after, by dialyse remove not with rice egg
The free forulic acid combined in vain, then be freeze-dried to obtain rice protein/forulic acid compound or rice protein/ferulic acid crosslinks
Thing.
The preparation method of the rice protein is as follows,
(1) rice meal of degreasing is pressed 1:10 (w/v) solid-liquid ratio is dispersed in water, and is uniformly mixing to obtain rice meal and is disperseed
Liquid,
(2) pH of rice meal dispersion liquid is adjusted to 10.0,25 DEG C of stirring 2h of room temperature, then centrifuges to obtain supernatant,
(3) supernatant pH is adjusted to 4.8 and obtains protein precipitation, protein precipitation adds water to obtain protein liquid, protein liquid
Rice protein is obtained after neutralized, dialysis, freeze-drying.
Rice protein/forulic acid/laccase Compound mixed solution the method is as follows：
(1) rice protein is dissolved in pH=7.0,50mmol/L PBS, stirring makes it fully dissolve to obtain
Rice protein dispersion liquid；
(2) forulic acid is dissolved in pH=7.0,50mmol/L PBS, heating water bath promotes it completely molten
Solution, obtains asafoetide acid solution；
(3) rice protein dispersion liquid and asafoetide acid solution are well mixed, add laccase and stir, obtain rice egg
In vain/forulic acid/laccase mixed liquor.
In step (2), the reaction process condition of rice protein/forulic acid/laccase mixed liquor is as follows：Reaction temperature be 25~
30 DEG C, the reaction time is 0.5~4h.
In step (2), when the mass concentration of laccase in rice protein/forulic acid/laccase mixed liquor is not zero, work is reacted
Skill condition is as follows：Reaction temperature is 25~30 DEG C, and the reaction time is 3~4h.
In step (2), the process conditions of the dialysis are as follows：Temperature of dialysing is 4 DEG C, dialysis time 24h.
In step (1), the ratio between mass concentration of forulic acid and laccase is 4:1.
The preparation method of above-mentioned rice protein/forulic acid compound or cross-linking agent, when the addition of laccase is zero, obtain
Be rice protein/forulic acid compound, when the addition of laccase is not zero, to react, obtain because there occurs Enzymatic grafting
Be rice protein/ferulic acid crosslinks thing.
The present invention compared with the prior art, has the following advantages and beneficial effect：
(1) there is preferable antioxidation in vitro to live for the achievable continuous production of the present invention, rice protein/ferulic acid crosslinks thing
Property；It may be used on the strong medical treatment of some oxidation resistances, food and field of polymer technology.
(2) the inventive method is a kind of enzyme process means, gentle, safety；Experimental implementation is simple.
Embodiment
Embodiment 1
A kind of preparation method of rice protein/forulic acid compound, comprises the following steps：
(1) rice protein/forulic acid/laccase mixed liquor is prepared, in the rice protein/forulic acid/laccase mixed liquor, greatly
The mass concentration of rice gluten is 10mg/mL, and the mass concentration of forulic acid is 0.4mg/mL, and the mass concentration of laccase is 0mg/mL.
(2) after the agitated fully reaction of rice protein/forulic acid/laccase mixed liquor, reaction temperature is 25 DEG C, the reaction time
For 4h, the free forulic acid not combined with rice protein is removed by dialysing, dialysis temperature is 4 DEG C, dialysis time 24h, then
Freeze-drying obtains rice protein/forulic acid compound.
The preparation method of the rice protein is as follows,
(1) rice meal of degreasing is pressed 1:10 (w/v) solid-liquid ratio is dispersed in water, and is uniformly mixing to obtain rice meal and is disperseed
Liquid,
(2) pH of rice meal dispersion liquid is adjusted to 10.0,25 DEG C of stirring 2h of room temperature, then centrifuges to obtain supernatant,
(3) supernatant pH is adjusted to 4.8 and obtains protein precipitation, protein precipitation adds water to obtain protein liquid, protein liquid
Rice protein is obtained after neutralized, dialysis, freeze-drying.
Rice protein/forulic acid/laccase Compound mixed solution the method is as follows：
(1) rice protein is dissolved in pH=7.0,50mmol/L PBS, stirring makes it fully dissolve to obtain
Rice protein dispersion liquid；
(2) forulic acid is dissolved in pH=7.0,50mmol/L PBS, heating water bath promotes it completely molten
Solution, obtains asafoetide acid solution；
(3) rice protein dispersion liquid and asafoetide acid solution are well mixed, add laccase and stir, obtain rice egg
In vain/forulic acid/laccase mixed liquor.
The index of the embodiment 1 of table 1
As it can be seen from table 1 the rice protein scavenging ability of DPPH free radical (32.305%) that compares, rice protein and Ah
Wei's acid increases to 46.578% with reference to rear scavenging ability of DPPH free radical, and TAC index (removes ABTS free radical energy
Power and oxygen radical absorbability ORAC) equally it is higher than untreated rice protein, illustrate rice protein/forulic acid in natural bar
The antioxidation activity of the compound improvement rice protein of the rice protein/forulic acid formed under part.
Embodiment 2
A kind of preparation method of rice protein/ferulic acid crosslinks thing, comprises the following steps：
(1) rice protein/forulic acid/laccase mixed liquor is prepared, in the rice protein/forulic acid/laccase mixed liquor, greatly
The mass concentration of rice gluten is 10mg/mL, and the mass concentration of forulic acid is 0.4mg/mL, and the mass concentration of laccase is 0.1mg/
mL。
(2) after the agitated fully reaction of rice protein/forulic acid/laccase mixed liquor, reaction temperature is 25 DEG C, the reaction time
For 4h, the free forulic acid not combined with rice protein is removed by dialysing, dialysis temperature is 4 DEG C, dialysis time 24h, then
Freeze-drying obtains rice protein/ferulic acid crosslinks thing.
The preparation method of the rice protein is as follows,
(1) rice meal of degreasing is pressed 1:10 (w/v) solid-liquid ratio is dispersed in water, and is uniformly mixing to obtain rice meal and is disperseed
Liquid,
(2) pH of rice meal dispersion liquid is adjusted to 10.0,25 DEG C of stirring 2h of room temperature, then centrifuges to obtain supernatant,
(3) supernatant pH is adjusted to 4.8 and obtains protein precipitation, protein precipitation adds water to obtain protein liquid, protein liquid
Rice protein is obtained after neutralized, dialysis, freeze-drying.
Rice protein/forulic acid/laccase Compound mixed solution the method is as follows：
(1) rice protein is dissolved in pH=7.0,50mmol/L PBS, stirring makes it fully dissolve to obtain
Rice protein dispersion liquid；
(2) forulic acid is dissolved in pH=7.0,50mmol/L PBS, heating water bath promotes it completely molten
Solution, obtains asafoetide acid solution；
(3) rice protein dispersion liquid and asafoetide acid solution are well mixed, add laccase and stir, obtain rice egg
In vain/forulic acid/laccase mixed liquor.
The index of the embodiment 2 of table 2
From table 2 it can be seen that after Laccase Catalyzed oxidation forulic acid is grafted to rice protein particulate, rice protein/forulic acid
Cross-linking agent scavenging ability of DPPH free radical is 71.431%, is significantly higher than rice protein (32.305%) and rice protein/asafoetide
Sour compound (46.578%), illustrate that Laccase Catalyzed rice protein/ferulic acid crosslinks have higher antioxidation activity, it may be possible to
Because rice protein/ferulic acid crosslinks have bound the oh group of more forulic acids.Remove ABTS free radicals ability and oxygen certainly
It is consistent with scavenging ability of DPPH free radical by base absorbability ORAC result trend, therefore, addition Laccase Catalyzed rice protein with
The cross-linking agent that the combination of forulic acid obtains has higher antioxidation activity.
Embodiment 3
A kind of preparation method of rice protein/ferulic acid crosslinks thing, comprises the following steps：
(1) rice protein/forulic acid/laccase mixed liquor is prepared, the present embodiment carries out the contrast test of five gradients, each
In rice protein/forulic acid/laccase mixed liquor of experiment, the mass concentration of rice protein is 10mg/mL, the quality of forulic acid
Concentration is respectively 0mg/mL, 0.05mg/mL, 0.1mg/mL, 0.2mg/mL and 0.4mg/mL, the quality of laccase in each experiment
Concentration is a quarter of the mass concentration of corresponding forulic acid.
(2) after the agitated fully reaction of rice protein/forulic acid/laccase mixed liquor, reaction temperature is 25 DEG C, the reaction time
For 4h, the free forulic acid not combined with rice protein is removed by dialysing, dialysis temperature is 4 DEG C, dialysis time 24h, then
Freeze-drying obtains rice protein/forulic acid compound or rice protein/ferulic acid crosslinks thing.
The preparation method of the rice protein is as follows,
(1) rice meal of degreasing is pressed 1:10 (w/v) solid-liquid ratio is dispersed in water, and is uniformly mixing to obtain rice meal and is disperseed
Liquid,
(2) pH of rice meal dispersion liquid is adjusted to 10.0,25 DEG C of stirring 2h of room temperature, then centrifuges to obtain supernatant,
(3) supernatant pH is adjusted to 4.8 and obtains protein precipitation, protein precipitation adds water to obtain protein liquid, protein liquid
Rice protein is obtained after neutralized, dialysis, freeze-drying.
Rice protein/forulic acid/laccase Compound mixed solution the method is as follows：
(1) rice protein is dissolved in pH=7.0,50mmol/L PBS, stirring makes it fully dissolve to obtain
Rice protein dispersion liquid；
(2) forulic acid is dissolved in pH=7.0,50mmol/L PBS, heating water bath promotes it completely molten
Solution, obtains asafoetide acid solution；
(3) rice protein dispersion liquid and asafoetide acid solution are well mixed, add laccase and stir, obtain rice egg
In vain/forulic acid/laccase mixed liquor.
The index of the embodiment 3 of table 3
From table 3 it can be seen that rice protein scavenging ability of DPPH free radical, removing ABTS free radicals ability, ORAC values point
Not Wei and 32.305%, 3.342% and 0.695 μM of trolox/g, with the increase of asafoetide acid concentration, rice protein (RP) with
The scavenging ability of DPPH free radical of forulic acid (FA) mixed liquor, remove ABTS free radicals ability, oxygen radical absorbability ORAC
Value all significantly improves, and has significant oxidation resistance mainly due to the forulic acid to dissociate in mixed liquor.Laccase Catalyzed asafoetide
Acid declined with oxidation resistance after rice protein covalent bond compared with the oxidation resistance in mixed liquor, this be due to DPPH oneself
The oxidation resistance determined in method, the mainly system of ABTS radicals scavengings method measure by the polyphenol that dissociates, asafoetide are removed by base
Acid is easily aoxidized by Laccase Catalyzed, therefore the covalent interaction of albumen/polyphenol is substantially that these abilities slacken.But rice egg
The antioxidation activity of in vain/ferulic acid crosslinks thing is higher than untreated rice protein (RP), it is possible the reason for be forulic acid oxidation
Product can react with amino in rice protein and sulfydryl, so as to be grafted on rice protein molecule, while remain Ah
The antioxidation activity group of Wei's acid.Finally, when the addition of forulic acid reaches 0.4mg/mL, antioxidation activity value reaches most
Greatly, the rice protein/ferulic acid crosslinks thing prepared using this condition has higher antioxidation activity.
Embodiment 4
A kind of preparation method of rice protein/ferulic acid crosslinks thing, comprises the following steps：
(1) rice protein/forulic acid/laccase mixed liquor is prepared, in the rice protein/forulic acid/laccase mixed liquor, greatly
The mass concentration of rice gluten is 8mg/mL, and the mass concentration of forulic acid is 0.1mg/mL, and the mass concentration of laccase is 0.025mg/
mL。
(2) after the agitated fully reaction of rice protein/forulic acid/laccase mixed liquor, reaction temperature is 25 DEG C, the reaction time
For 4h, the free forulic acid not combined with rice protein is removed by dialysing, dialysis temperature is 4 DEG C, dialysis time 24h, then
Freeze-drying obtains rice protein/forulic acid compound or rice protein/ferulic acid crosslinks thing.
Embodiment 5
A kind of preparation method of rice protein/forulic acid compound, comprises the following steps：
(1) rice protein/forulic acid/laccase mixed liquor is prepared, in the rice protein/forulic acid/laccase mixed liquor, greatly
The mass concentration of rice gluten is 12mg/mL, and the mass concentration of forulic acid is 0.2mg/mL.
(2) after the agitated fully reaction of rice protein/forulic acid/laccase mixed liquor, reaction temperature is 25 DEG C, the reaction time
For 4h, the free forulic acid not combined with rice protein is removed by dialysing, dialysis temperature is 4 DEG C, dialysis time 24h, then
Freeze-drying obtains rice protein/forulic acid compound or rice protein/ferulic acid crosslinks thing.
Claims (7)
1. the preparation method of a kind of rice protein/forulic acid compound or cross-linking agent, it is characterised in that comprise the following steps：
（1）Prepare rice protein/forulic acid/laccase mixed liquor, in the rice protein/forulic acid/laccase mixed liquor, rice egg
White mass concentration is 8~12 mg/mL, and the mass concentration of forulic acid is 0.05~0.4 mg/mL, and the quality of laccase is dense
Spend for 0~0.1 mg/mL,
（2）Rice protein/forulic acid/laccase mixed liquor it is agitated fully reaction after, by dialyse remove not with rice protein knot
The free forulic acid closed, then be freeze-dried to obtain rice protein/forulic acid compound or rice protein/ferulic acid crosslinks thing.
2. preparation method as claimed in claim 1, it is characterised in that the preparation method of the rice protein is as follows,
（1）The rice meal of degreasing is pressed 1:10 w/v solid-liquid ratios are dispersed in water, and are uniformly mixing to obtain rice meal dispersion liquid,
（2）The pH of rice meal dispersion liquid is adjusted to 10.0,25 DEG C of 2 h of stirring of room temperature, then centrifuges to obtain supernatant,
（3）Supernatant pH is adjusted to 4.8 and obtains protein precipitation, protein precipitation adds water to obtain protein liquid, during protein liquid passes through
With, dialysis, freeze-drying after obtain rice protein.
3. preparation method as claimed in claim 1, it is characterised in that the rice protein/forulic acid/laccase Compound mixed solution
Method is as follows：
（1）By rice protein be dissolved in pH=7.0,50 mmol/L PBS in, stirring make its fully dissolve to obtain it is big
Rice gluten dispersion liquid；
（2）By forulic acid be dissolved in pH=7.0,50 mmol/L PBS in, heating water bath promotes it to be completely dissolved,
Obtain asafoetide acid solution；
（3）Rice protein dispersion liquid and asafoetide acid solution are well mixed, laccase is added and stirs, obtain rice protein/
Forulic acid/laccase mixed liquor.
4. preparation method according to claim 1, it is characterised in that step（2）In, rice protein/forulic acid/laccase mixing
The reaction process condition of liquid is as follows：Reaction temperature is 25~30 DEG C, and the reaction time is 0.5~4 h.
5. preparation method according to claim 1, it is characterised in that step（2）In, when rice protein/forulic acid/laccase mixes
When the mass concentration of laccase is not zero in conjunction liquid, reaction process condition is as follows：Reaction temperature be 25 ~ 30 DEG C, the reaction time be 3 ~
4 h。
6. preparation method according to claim 1, it is characterised in that step（2）In, the process conditions of the dialysis are as follows：
Temperature of dialysing is 4 DEG C, and dialysis time is 24 h.
7. preparation method according to claim 1, it is characterised in that step（1）In, the mass concentration of forulic acid and laccase it
Than for 4:1.
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| CN108719575A (en) * | 2017-04-19 | 2018-11-02 | 东北农业大学 | A method of improving α-lactalbumin functional characteristic and antioxidant activity |
| CN108030025A (en) * | 2017-12-08 | 2018-05-15 | 周起行 | The production method that a kind of antibacterial pickles radish |
| CN107811245A (en) * | 2017-12-08 | 2018-03-20 | 周起行 | A kind of preparation method of low-salt pickled radish |
| CN108719999B (en) * | 2018-05-07 | 2022-04-19 | 中国农业大学 | Preparation method and application of protein-polyphenol-polysaccharide covalent compound |
| CN115444141A (en) * | 2021-06-08 | 2022-12-09 | 天津大学 | High oxidation resistance soybean protein isolate-gallic acid compound and preparation method thereof |
| CN116391789A (en) * | 2023-04-13 | 2023-07-07 | 东北农业大学 | Method for improving functional characteristics of glycinin by low-pressure homogenization assisted non-covalent ferulic acid compounding |
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| CN101253925A (en) * | 2008-04-01 | 2008-09-03 | 江南大学 | Preparation of rice protein antioxidation active peptide |
| CN102845710A (en) * | 2011-05-12 | 2013-01-02 | 格里菲思实验室国际有限公司 | Method for preparing a proteinaceous vegetable flavor enhancer |
| CN103339260A (en) * | 2011-01-04 | 2013-10-02 | 诺维信公司 | Process for producing biogas from pectin and lignocellulose containing material |
| CN104047184A (en) * | 2014-06-09 | 2014-09-17 | 江南大学 | Method for catalyzing and oxidizing tyrosine through laccase |
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| CN101253925A (en) * | 2008-04-01 | 2008-09-03 | 江南大学 | Preparation of rice protein antioxidation active peptide |
| CN103339260A (en) * | 2011-01-04 | 2013-10-02 | 诺维信公司 | Process for producing biogas from pectin and lignocellulose containing material |
| CN102845710A (en) * | 2011-05-12 | 2013-01-02 | 格里菲思实验室国际有限公司 | Method for preparing a proteinaceous vegetable flavor enhancer |
| CN104047184A (en) * | 2014-06-09 | 2014-09-17 | 江南大学 | Method for catalyzing and oxidizing tyrosine through laccase |
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