CN106755158A - A kind of method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid - Google Patents
A kind of method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid Download PDFInfo
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- CN106755158A CN106755158A CN201611188565.2A CN201611188565A CN106755158A CN 106755158 A CN106755158 A CN 106755158A CN 201611188565 A CN201611188565 A CN 201611188565A CN 106755158 A CN106755158 A CN 106755158A
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
- C12P13/227—Tryptophan
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
- C12P13/222—Phenylalanine
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
- C12P13/225—Tyrosine; 3,4-Dihydroxyphenylalanine
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Abstract
The present invention relates to the recovery method of amino acid, and in particular to a kind of method that aromatic amino acid is reclaimed in leftover bits and pieces from squid.It comprises the following steps：By squid leftover bits and pieces enzymolysis, enzymolysis liquid is obtained；Absorption aromatic amino acid obtains activated carbon 2 during activated carbon 1 is added into enzymolysis liquid；Activated carbon 2 is added in strippant, is sealed after quickly stirring, desorption 120min 180min are stood at 40 70 DEG C, supernatant is taken after being then centrifuged for；Supernatant vacuum distillation is obtained into aromatic amino acid.The present invention extracts the aromatic amino acid of needed by human body using the ethanol and ethyl acetate solution of food-grade from squid leftover bits and pieces, and desorption is carried out to target amino acid and the principle with vacuum distillation isolates and purifies aromatic amino acid, the aromatic amino acid of the recycling is set to apply in food, realize green, the target of environmental protection, and reclaiming that the aromatic amino acid purity that obtains is high, high income, the amino acid is good to human body.
Description
Technical field
The present invention relates to the recovery method of amino acid, and in particular to one kind reclaims aromatic amino acid from squid leftover bits and pieces
Method.
Background technology
In the process of squid, substantial amounts of leftover bits and pieces can be produced, its weight accounts for the 20-40% of total amount.If no
It is effectively treated, not only pollutes the environment, and substantial amounts of nutriment can be wasted.For the utilization of leftover bits and pieces, mainly have
Production squid powder, not yet makes full use of to wherein valuable composition.
And phenylalanine and tyrosine are respectively the essential amino acid and semi-dispensable amino acid of human body, can be sought as amino acid
Foster replenisher is widely used in the industries such as agricultural, fishery, medicine, food, reclaim in addition amino acid raw material is cheap, technique is simple
It is single, therefore application prospect is extensive.
F values (Fischer ratio), are branched-chain amino acid (BCAA:Val, Ile, Leu) and aromatic amino acid (AAA:
Trp, Tyr, Phe) content molal quantity ratio, in F oligopeptides technique high is prepared, commonly use activated carbon from enzymolysis liquid specificity inhale
Attached aromatic amino acid carries high F value.Extensive purposes is had in food, medical industry based on aromatic amino acid, it is existing
The certain methods layer such as wash-out recovery is carried out to aromatic amino acid using ammoniacal liquor, the parsing of ethanol substep and NaOH solution in report
Go out not poor.But because above-mentioned classification solvent has toxicity and lacks eluent and separation for amino acids, because
Be difficult to for the purification of wherein aromatic amino acid by this, therefore can not realize aromatic amino acid answering in daily bread processing
With.
The content of the invention
The purpose of the present invention is directed to the above-mentioned problems in the prior art, it is proposed that safety, simple and easy to apply from squid
The method that aromatic amino acid is reclaimed in fish pomace.
Above-mentioned purpose of the invention is achieved through the following technical solutions：One kind reclaims aromatic series amino from squid leftover bits and pieces
The method of acid, described method comprises the following steps：
S1, by squid leftover bits and pieces enzymolysis, obtain enzymolysis liquid；
S2, activated carbon 1 is added in enzymolysis liquid and adsorbs aromatic amino acid and obtain activated carbon 2；
S3, activated carbon 2 is added in strippant, is sealed after quickly stirring, desorption 210- is stood at 40-70 DEG C
270min, supernatant is taken after being then centrifuged for；
S4, supernatant vacuum distillation is obtained into aromatic amino acid.
Dissolution characteristics, polarity of the present invention by aromatic amino acid, from the efficient strippant of safety and low toxicity to from squid
The activated carbon that aromatic amino acid has been adsorbed in fish pomace enzymolysis liquid is eluted, and it is few that centrifugation gained supernatant is high F value
Peptide solution, is then obtained aromatic amino acid using water-bath evaporation, crystallization, can be answered in the production and processing of food
With.And the boiling point of phenylalanine is 295 DEG C in aromatic amino acid, tyrosine is 342-344 DEG C, 289 DEG C of tryptophan, and ethanol is molten
Liquid boiling point is 78.4 DEG C, and ethyl acetate boiling point is 77 DEG C.The boiling point of liquid refer to its vapour pressure be equal to ambient pressure when temperature
Degree, therefore the boiling point of liquid is changed with the change of ambient pressure, vacuum distillation is by means of vavuum pump reduction system internal pressure
Power, the boiling point of liquid is reduced with this.Therefore vacuum distillation separation can be carried out to stripping liquid according to boiling point difference, more rapid and better
To purifying aromatic amino acid.
Preferably, what is digested described in step S1 concretely comprises the following steps：Squid leftover bits and pieces is compared 1 by material water quality：4-6 is equal
Slurry, then adjusts pH to 2, to expect that enzyme compares 8-10 with HCl by homogenate：1 adds pepsin, in 40-50 DEG C of water bath with thermostatic control concussion water
Solution 4-6h, after the completion of gone out enzyme 10-20min with boiling water bath, pH to 7 is adjusted again after being then cooled to normal temperature, with solid-liquid ratio 15-
25：1 adds food flavor enzyme, in 50-60 DEG C of water bath with thermostatic control concussion hydrolysis 2-4h, after the completion of gone out enzyme 10-20min with boiling water bath, then enter
Row is filtered and obtains enzymolysis liquid.
Preferably, step S2 is specially：Activated carbon 1 is first activated into 1-3h before enzymolysis liquid is added at 100-110 DEG C,
The activated carbon 1 after activation is added in the enzymolysis liquid that pH value is 2 again, absorption 15-25min is shaken in 30-40 DEG C of water-bath,
Obtain activated carbon 2.
Further preferably, described activated carbon 1 is 1 with the mass ratio of enzymolysis liquid：20-30.
Preferably, the strippant described in step S3 includes ethanol and ethyl acetate.Used with single in the prior art
Ethanol reclaims aromatic amino acid, and the present invention is cooked strippant and reclaimed aromatic amine from adsorbent 2 from ethanol and ethyl acetate
Base acid, substantially increases its desorption degree, and ethyl acetate as food additives, the amino acid obtained by recovery preferably should
In food.
Further preferably, described ethanol and the volume ratio of ethyl acetate are 0.5-1.5：1.The present invention is by second in strippant
If the volume ratio control of alcohol and ethyl acetate is that amount of alcohol is very few in the present invention in above range its reason to cause to mix solution
Imbibition can not dissolve each other very well, influence desorption efficiency, if amount of alcohol excessively makes method be partial to single ethanol recovery can equally reduce
Desorption efficiency, strippant of the invention is ethanol and ethyl acetate collective effect, promotes final desorption efficiency, is not ethyl acetate
Only serve the effect of stimulant.
Still further preferably, the concentration of the ethanol is 40-70%.
Preferably, the addition of activated carbon 2 and the ratio of strippant are 0.2-0.4g/10ml in step S3.If desorption
The amount of agent is very few, the easy saturation of strippant, causes amino acid impaired performance in desorption activated carbon；If the amount of strippant is excessive, when molten
When agent reaches a certain amount of, amino acid excessively will not be desorbed out from activated carbon, excessive only to cause to waste, and improve
Cost.
Preferably, the rotating speed being centrifuged in step S3 is 4000-4500r/min, centrifugation time is 3-8min.
It is added to the aromatic amino acid for obtaining is reclaimed by the above method in food.
Compared with prior art, the present invention is extracted using the ethanol and ethyl acetate solution of food-grade from squid leftover bits and pieces
Go out the aromatic amino acid of needed by human body, and desorption is carried out to target amino acid and the principle with vacuum distillation is isolated and purified
Aromatic amino acid, allows the aromatic amino acid of the recycling to apply in food, realizes green, the mesh of environmental protection
Mark, and reclaim that the aromatic amino acid purity that obtains is high, high income, the amino acid is good to human body.
Specific embodiment
The following is specific embodiment of the invention, technical scheme is further described, but the present invention is simultaneously
It is not limited to these embodiments.
Embodiment 1
Squid leftover bits and pieces is compared 1 by material water quality：5 homogenates, then adjust pH to 2, to expect that enzyme compares 9 with HCl by homogenate：1 adds
Enter pepsin, in 45 DEG C of waters bath with thermostatic control concussion hydrolysis 5h, after the completion of gone out enzyme 15min with boiling water bath, after being then cooled to normal temperature
PH to 7 is adjusted again, with solid-liquid ratio 18：1 adds food flavor enzyme, in 55 DEG C of waters bath with thermostatic control concussion hydrolysis 3h, after the completion of with boiling water bath
Go out enzyme 15min, then filter obtaining enzymolysis liquid.
Activated carbon 1 is first activated into 2h before enzymolysis liquid is added at 105 DEG C, then the activated carbon 1 after activation is added to pH
It is worth in the enzymolysis liquid for 2 that (ratio of activated carbon 1 and enzymolysis liquid is 1：25) absorption 20min, is shaken in 35 DEG C of water-bath, work is obtained
Property charcoal 2.
During activated carbon 2 is added into strippant (addition of activated carbon 2 is 0.3g/10ml with the content ratio of strippant),
Sealed after quickly stirring, desorption 240min is stood at 60 DEG C, 5min then is centrifuged under rotating speed 4200r/min, taken
Clear liquid；Described strippant is ethanol and ethyl acetate by volume 1.0：The concentration of 1 mixture, wherein ethanol is 60%.
The aromatic amino acid that supernatant vacuum distillation must can be used in food.And Trp in aromatic amino acid,
Tyr and Phe contents are respectively：Trp 0.0732mg/mL、Tyr 0.3283mg/mL、Phe 0.4100mg/mL.
Embodiment 2
Squid leftover bits and pieces is compared 1 by material water quality：5 homogenates, then adjust pH to 2, to expect that enzyme compares 8 with HCl by homogenate：1 adds
Enter pepsin, in 42 DEG C of waters bath with thermostatic control concussion hydrolysis 4h, after the completion of gone out enzyme 18min with boiling water bath, after being then cooled to normal temperature
PH to 7 is adjusted again, with solid-liquid ratio 22：1 adds food flavor enzyme, in 52 DEG C of waters bath with thermostatic control concussion hydrolysis 4h, after the completion of with boiling water bath
Go out enzyme 18min, then filter obtaining enzymolysis liquid.
Activated carbon 1 is first activated into 2h before enzymolysis liquid is added at 108 DEG C, then the activated carbon 1 after activation is added to pH
It is worth in the enzymolysis liquid for 2 that (ratio of activated carbon 1 and enzymolysis liquid is 1：22) absorption 22min, is shaken in 32 DEG C of water-bath, work is obtained
Property charcoal 2.
During activated carbon 2 is added into strippant (addition of activated carbon 2 is 0.32g/10ml with the content ratio of strippant),
Sealed after quickly stirring, desorption 260min is stood at 50 DEG C, 4min then is centrifuged under rotating speed 4400r/min, taken
Clear liquid；Described strippant is ethanol and ethyl acetate by volume 0.8：The concentration of 1 mixture, wherein ethanol is 50%.
The aromatic amino acid that supernatant vacuum distillation must can be used in food.And Trp in aromatic amino acid,
Tyr and Phe contents are respectively：Trp 0.0621mg/mL、Tyr 0.3168mg/mL、Phe 0.3450mg/mL.
Embodiment 3
Squid leftover bits and pieces is compared 1 by material water quality：4 homogenates, then adjust pH to 2, to expect that enzyme compares 9 with HCl by homogenate：1 adds
Enter pepsin, in 48 DEG C of waters bath with thermostatic control concussion hydrolysis 6h, after the completion of gone out enzyme 12min with boiling water bath, after being then cooled to normal temperature
PH to 7 is adjusted again, with solid-liquid ratio 25：1 adds food flavor enzyme, in 58 DEG C of waters bath with thermostatic control concussion hydrolysis 2h, after the completion of with boiling water bath
Go out enzyme 10min, then filter obtaining enzymolysis liquid.
Activated carbon 1 is first activated into 3h before enzymolysis liquid is added at 100 DEG C, then the activated carbon 1 after activation is added to pH
It is worth in the enzymolysis liquid for 2 that (ratio of activated carbon 1 and enzymolysis liquid is 1：28) absorption 25min, is shaken in 30 DEG C of water-bath, work is obtained
Property charcoal 2.
During activated carbon 2 is added into strippant (addition of activated carbon 2 is 0.2g/10ml with the content ratio of strippant),
Sealed after quickly stirring, desorption 210min is stood at 70 DEG C, 8min then is centrifuged under rotating speed 4000r/min, taken
Clear liquid；Described strippant is ethanol and ethyl acetate by volume 0.5：The concentration of 1 mixture, wherein ethanol is 40%.
The aromatic amino acid that supernatant vacuum distillation must can be used in food.And Trp in aromatic amino acid,
Tyr and Phe contents are respectively：Trp 0.0593mg/mL、Tyr 0.3318mg/mL、Phe 0.3509mg/mL.
Embodiment 4
Squid leftover bits and pieces is compared 1 by material water quality：6 homogenates, then adjust pH to 2, to expect that enzyme compares 10 with HCl by homogenate：1 adds
Enter pepsin, in 40 DEG C of waters bath with thermostatic control concussion hydrolysis 4h, after the completion of gone out enzyme 20min with boiling water bath, after being then cooled to normal temperature
PH to 7 is adjusted again, with solid-liquid ratio 15：1 adds food flavor enzyme, in 60 DEG C of waters bath with thermostatic control concussion hydrolysis 2h, after the completion of with boiling water bath
Go out enzyme 20min, then filter obtaining enzymolysis liquid.
Activated carbon 1 is first activated into 1h before enzymolysis liquid is added at 110 DEG C, then the activated carbon 1 after activation is added to pH
It is worth in the enzymolysis liquid for 2 that (ratio of activated carbon 1 and enzymolysis liquid is 1：30) absorption 15min, is shaken in 40 DEG C of water-bath, work is obtained
Property charcoal 2.
During activated carbon 2 is added into strippant (addition of activated carbon 2 is 0.4g/10ml with the content ratio of strippant),
Sealed after quickly stirring, desorption 270min is stood at 40 DEG C, 3min then is centrifuged under rotating speed 4500r/min, taken
Clear liquid；Described strippant is ethanol and ethyl acetate by volume 1.5：The concentration of 1 mixture, wherein ethanol is 70%.
The aromatic amino acid that supernatant vacuum distillation must can be used in food.And Trp in aromatic amino acid,
Tyr and Phe contents are respectively：Trp 0.0543mg/mL、Tyr 0.3128mg/mL、Phe 0.3280mg/mL.
Comparative example 1
Wash-out recovery is carried out to aromatic amino acid with NaOH solution, Trp, Tyr in the aromatic amino acid for obtaining and
Phe contents are respectively：Trp 0.0493mg/mL、Tyr 0.2098mg/mL、Phe 0.3000mg/mL.
Specific embodiment described herein is only to the spiritual explanation for example of the present invention.Technology neck belonging to of the invention
The technical staff in domain can be made various modifications or supplement to described specific embodiment or be substituted using similar mode, but simultaneously
Do not deviate by spirit of the invention or surmount scope defined in appended claims.
It is skilled to this area although having made a detailed description and being cited some specific embodiments to the present invention
For technical staff, as long as it is obvious that can be made various changes without departing from the spirit and scope of the present invention or corrected.
Claims (9)
1. a kind of method that aromatic amino acid is reclaimed in leftover bits and pieces from squid, it is characterised in that described method includes as follows
Step：
S1, by squid leftover bits and pieces enzymolysis, obtain enzymolysis liquid；
S2, activated carbon 1 is added in enzymolysis liquid and adsorbs aromatic amino acid and obtain activated carbon 2；
S3, activated carbon 2 is added in strippant, is sealed after quickly stirring, desorption 210- is stood at 40-70 DEG C
270min, supernatant is taken after being then centrifuged for；
S4, supernatant vacuum distillation is obtained into aromatic amino acid.
2. the method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid according to claim 1, it is characterised in that step
What is digested described in S1 concretely comprises the following steps：Squid leftover bits and pieces is compared 1 by material water quality：4-6 homogenates, are then adjusted homogenate with HCl
PH to 2, to expect that enzyme compares 8-10：1 adds pepsin, in 40-50 DEG C of water bath with thermostatic control concussion hydrolysis 4-6h, after the completion of with boiling water bath
Gone out enzyme 10-20min, and pH to 7 is adjusted again after being then cooled to normal temperature, with solid-liquid ratio 15-25：1 adds food flavor enzyme, in 50-60
DEG C water bath with thermostatic control concussion hydrolysis 2-4h, after the completion of gone out enzyme 10-20min with boiling water bath, then filter obtaining enzymolysis liquid.
3. the method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid according to claim 1, it is characterised in that step
S2's concretely comprises the following steps：Activated carbon 1 is first activated into 1-3h before enzymolysis liquid is added at 100-110 DEG C, then by the work after activation
Property charcoal 1 be added in the enzymolysis liquid that pH value is 2, in 30-40 DEG C of water-bath shake absorption 15-25min, obtain activated carbon 2.
4. the method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid according to claim 3, it is characterised in that described
The mass ratio of activated carbon 1 and enzymolysis liquid be 1：20-30.
5. the method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid according to claim 1, it is characterised in that step
Strippant described in S3 includes ethanol and ethyl acetate.
6. the method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid according to claim 5, it is characterised in that described
The volume ratio of ethanol and ethyl acetate be 0.5-1.5：1.
7. the method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid according to claim 6, it is characterised in that described
The concentration of ethanol is 40-70%.
8. the method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid according to claim 1, it is characterised in that step
The addition of activated carbon 2 and the ratio of strippant are 0.2-0.4g/10ml in S3.
9. the method that aromatic amino acid is reclaimed in the leftover bits and pieces from squid according to claim 1, it is characterised in that step
The rotating speed being centrifuged in S3 is 4000-4500r/min, and centrifugation time is 3-8min.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108056408A (en) * | 2017-11-15 | 2018-05-22 | 浙江海洋大学 | A kind of aminophenol nutrient and preparation method rich in taurine |
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| CN108056408A (en) * | 2017-11-15 | 2018-05-22 | 浙江海洋大学 | A kind of aminophenol nutrient and preparation method rich in taurine |
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Application publication date: 20170531 |