CN107226835A - Savoury peptide, dense taste imparting agent and its flavoring and preparation method - Google Patents
Savoury peptide, dense taste imparting agent and its flavoring and preparation method Download PDFInfo
- Publication number
- CN107226835A CN107226835A CN201710511184.1A CN201710511184A CN107226835A CN 107226835 A CN107226835 A CN 107226835A CN 201710511184 A CN201710511184 A CN 201710511184A CN 107226835 A CN107226835 A CN 107226835A
- Authority
- CN
- China
- Prior art keywords
- glu
- tyr
- cys
- oligopeptides
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
-
- 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
- C12P21/00—Preparation of peptides or proteins
- C12P21/02—Preparation of peptides or proteins having a known sequence of two or more amino acids, e.g. glutathione
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Medicinal Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Seasonings (AREA)
Abstract
The invention discloses savoury peptide γ Glu γ Glu γ Glu Tyr, dense taste imparting agent and its flavoring and preparation method.The amino acid sequence of the oligopeptides γ Glu γ Glu γ Glu Tyr is γ Glu γ Glu γ Glu Tyr.Dense taste imparting agent is made up of the oligopeptides and other peptides.The flavoring contains more than 330mg/kg γ Glu γ Glu γ Glu Tyr.This γ glutamine peptides γ Glu γ Glu Ile are remarkably improved the savoury of food particularly flavouring under 330mg/kg concentration.
Description
Technical field
The present invention relates to the peptide with flavor effect, and in particular to γ-Glutamyl Peptide and its application with savoury.
Background technology
γ-Glutamyl Peptide is deposited with a variety of animals and plants and fermented food, being that a kind of safety is natural extensively, safety food into
Point.Its primary structure of common glutathione is γ-Glu-Cys-Gly, is a kind of typical γ-Glutamyl Peptide.Modern study
Show that γ-Glutamyl Peptide is relevant with the metabolic activity and physiological function of organism, most of γ-Glutamyl Peptide has calm in addition
Depressurize, fatigue of releiving, anticancer removing toxic substances, complexation heavy metal ion, maintain cellular metal ions balance etc. physiological function.
In recent years, it has been found that γ-Glutamyl Peptide also has stronger flavor characteristic.Japanese aginomoto strain formula meeting in 2002
Society is disclosed by exploring the diversified compound with CaSR agonist activities, finds to assign with more excellent dense taste
Effect, the dense taste imparting effect particularly with preceding taste type, and with excellent stability, can be easy and produce at low cost
The material for being capable of imparting body taste with other there is CaSR to swash there is provided the dense taste imparting agent comprising the material, and by the material
The combinations of substances of dynamic agent activity using compound dense taste imparting agent.Include γ-Glu-Abu (L- gamma-glutamyl-L-2- ammonia
Base butyric acid) dense taste imparting agent, and the material with other have the combinations of substances of CaSR agonist activities using answer
Close dense taste imparting agent (number of patent application 201080024054.1).
Most of γ-Glutamyl Peptide under low consistency conditions has slight astringent taste, with the raising of concentration, γ-paddy ammonia
Acyl peptide starts that primary taste is presented.Such as γ-Glu-Glu have delicate flavour, γ-Glu-tyr bitter taste when concentration is 10mmol/L
Threshold value is twice of its astringent taste threshold value.In delicate flavour solution, γ-Glutamyl Peptide has savoury, and threshold value is also being decreased obviously.With
People further appreciate that scholar has found that γ-Glutamyl Peptide has the feature of savoury material to flavor peptide：1. base in aqueous
This insipidness or only slight taste (astringent taste or tart flavour)；2. increasing can be cooperateed with other taste compounds in system
Effect is acted on, and is added in the solution system containing delicate flavour material, will not change the basic taste sensation intensity of solution, but can coordinate each
Taste is planted, dense sense (kokumi) is dramatically increased；3. compared with pure water solution, threshold value is decreased obviously in delicate flavour solution.
Table 1 has reported γ-Glutamyl Peptide flavor characteristic and threshold value list
So far, there is not yet γ-Glu- γ-Glu- γ-Glu-Tyr have the report of dense taste.
The content of the invention
It is an object of the invention to overcome deficiencies of the prior art, there is provided one kind utilization glutamine enzymatic synthesis
The preparation method of γ-Glutamyl Peptide.
The purpose of the present invention is achieved through the following technical solutions.
A kind of oligopeptides, its amino acid sequence is γ-Glu- γ-Glu- γ-Glu-Tyr.
The dense taste imparting agent that the present invention is provided, is combined by the oligopeptides and more than one following peptide：γ-Glu-
X-Gly (X represents amino acid or amino acid derivativges), γ-Glu-Val-Y (Y represents amino acid or amino acid derivativges), γ-
Glu-Abu、γ-Glu-Ala、γ-Glu-Gly、γ-Glu-Cys、γ-Glu-Met、γ-Glu-Thr、γ-Glu-Val、γ-
Glu-Orn、Asp-Gly、Cys-Gly、Cys-Met、Glu-Cys、Gly-Cys、Leu-Asp、D-Cys、γ-Glu-Met(O)、
γ-Glu-γ-Glu-Val、γ-Glu-Val-NH2、γ-Glu-Val-ol、γ-Glu-Ser、γ-Glu-Tau、γ-Glu-
Cys (S-Me) (O), γ-Glu-Leu, γ-Glu-Ile, γ-Glu-t-Leu and γ-Glu-Cys (S-Me).
A kind of flavoring containing the oligopeptides, it contains more than 330mg/kg γ-Glu- γ-Glu- γ-Glu-Tyr
With.
A kind of flavoring containing the oligopeptides, the γ-Glu- γ-Glu- γ-Glu-Tyr containing more than 330mg/kg.
A kind of flavoring containing the oligopeptides, the γ-Glu- γ-Glu- γ-Glu-Tyr containing more than 1000mg/kg.
The preparation method of the oligopeptides, be specifically：Glutamine and free tyrosine, mol ratio are 1-2:1, it is soluble in water
Solution is obtained, regulation reaction pH is 7.0-10.0, adds glutaminase or gamma-glutamyl amine transpeptidase 0.02-1% (w/w),
25-50 DEG C is reacted 3-12 hour, between the rear pH to 7~8 with 4mol/L hydrochloric acid readjustment, 90 DEG C of enzyme 10min that go out, obtain containing γ-
Glu- γ-Glu- γ-Glu-Tyr reaction solution.Using 5 μm of 4.6x250mm analytical columns of XSelect HSS T3, mobile phase A
Liquid is 0.1% (V/V) formic acid-aqueous solution；Mobile phase B liquid is 0.1% (V/V) formic acid-acetonitrile solution, and column temperature is 40 DEG C, flow velocity
For 1mL/min, the μ L of sample size 10 of reaction solution, gradient elution is carried out to reaction solution using high performance liquid chromatography, appearance time is
5.530 peak is oligopeptides γ-Glu- γ-Glu- γ-Glu-Tyr.
Further, the concentration of the solution GLN is 400-1000mmol/L.
The present invention compared with prior art, has the following advantages that：
1) there is savoury characteristic present invention firstly discloses γ-Glu- γ-Glu- γ-Glu-Tyr.
2) make public for the first time and utilize glutaminase or gamma-glutamyl amine transpeptidase catalytic preparation of gamma-Glu- γ-Glu-
γ-Glu-Tyr。
Brief description of the drawings
Fig. 1 is the liquid chromatogram of mixture after reaction；
Fig. 2 is γ-Glu- γ-Glu- γ-Glu-Tyr second order mses figure.
Embodiment
Work further citing, but implementation of the invention and guarantor are specifically implemented to the present invention below in conjunction with accompanying drawing and example
Protect not limited to this.
Embodiment 1
By bacillus amyloliquefaciens (Bacillus amyloliquefaciens) SWJS22 (Chinese microorganism strain preservations
Administration committee's common micro-organisms center, deposit number is CGMCC No.8425, through in Chinese Patent Application No.
Have submitted preservation in 201510222162.4 application proves) fermentation medium (fermentation medium is inoculated in 1% inoculum concentration
Composition be：4% dregs of beans, 2% wheat bran, 2% corn flour) in, 37~39 DEG C of fermented and cultured 30h.By zymotic fluid in 4 DEG C,
High speed centrifugation 10min under the conditions of 10000r/min, filters to obtain supernatant, i.e. glutaminase crude enzyme liquid.
600mM glutamine and 600mM tyrosine are dissolved in 100g water, the pH value of solution is adjusted respectively to 9.0, is added
1g crude enzyme liquids, after 40 DEG C respectively reaction 12h, are adjusted back after pH to 7.0,90 DEG C of enzyme 10min that go out are contained with 4mol/L hydrochloric acid
γ-Glu- γ-Glu- γ-Glu-Tyr reaction solution.
Using 5 μm of 4.6x 250mm analytical columns of XSelect HSS T3, mobile phase A liquid is 0.1% (V/V) formic acid-water
Solution；Mobile phase B liquid is 0.1% (V/V) formic acid-acetonitrile solution, and column temperature is 40 DEG C, and flow velocity is 1mL/min, the sample introduction of reaction solution
10 μ L are measured, gradient elution (condition is carried out to reaction solution using high performance liquid chromatography：90% A liquid and 10% B liquid ladder during 0min
It is reduced in degree 5min in 85% A liquid and 15% B liquid, next 5min and is reduced to 20%A liquid and 80% B liquid).
5.530min peak is oligopeptides γ-Glu- γ-Glu- γ-Glu-Tyr.5.530min oligopeptides peak is collected, sense organ is carried out and comments
Valency and UPLC-MS/MS analyses.
UPLC-MS/MS carries out qualitative analysis to reaction product：Including：An Agilent 1290series UPLC
System (Agilent Technologies) is used to separate each γ-Glu-peptides, with an elec-trospray
Ionization (ESI) mass spectrometer system (Q-TOF MS/MS, Bruker Daltonics) carries out qualitative analysis.Chromatographic column is：
Agilent ZORBAX RRHD SB-C18(2.1 x 50mm,1.8μm).Sample size is 5 μ L.Liquid-phase condition is：Solution A is
0.1% formic acid-the aqueous solution, and solution B are 0.1% formic acid-acetonitrile solution, and gradient elution program is：0-10%B, 0-5.0min；
10-15%B, 5.0-10.0min；Then 100%B, 10.0-12.0min.MS conditions：Ionization (ionization)：Cation
Pattern；Drying gas (dry gas)：10L/min at 350 DEG C；Nebulizer (nebulizer pressure)：25psig；
Fragmentor (capillary voltage)：30V.UPLC-MS/MS analyses, its testing result such as Fig. 2 are carried out to gleanings.
As shown in Figure 2, its primary structure is γ-Glu- γ-Glu- γ-Glu-Tyr.
Embodiment 2
Bacillus subtillis ATCC 6633 is inoculated in the fermentation medium (composition of fermentation medium with 1% inoculum concentration
For：4% dregs of beans, 2% wheat bran, 2% corn flour) in, 37~39 DEG C of fermented and cultured 48h.By zymotic fluid in 4 DEG C, 10000r/min
Under the conditions of high speed centrifugation 10min, filter to obtain supernatant, i.e. gamma-glutamyl amine transpeptidase crude enzyme liquid.
600mM glutamine and 600mM tyrosine are dissolved in 100g water, the pH value of solution is adjusted respectively to 8.0, is added
1g gamma-glutamyl amine transpeptidase crude enzyme liquids, after 40 DEG C respectively reaction 6h, are adjusted back after pH to 7.0,90 DEG C go out with 4mol/L hydrochloric acid
Enzyme 10min, obtains the reaction solution rich in γ-Glu- γ-Glu- γ-Glu-Tyr.Using XSelect HSS T35 μm 4.6x
250mm analytical columns, mobile phase A liquid is 0.1% (V/V) formic acid-aqueous solution；Mobile phase B liquid is that 0.1% (V/V) formic acid-acetonitrile is molten
Liquid, column temperature is 40 DEG C, and flow velocity is 1mL/min, the μ L of sample size 10 of reaction solution, and ladder is carried out to reaction solution using high performance liquid chromatography
Degree elution, the oligopeptides peak for collecting 5.530min is γ-Glu- γ-Glu- γ-Glu-Tyr.
Embodiment 3
Add in 0.033% (g/g) γ-Glu- γ-Glu- γ-Glu-Tyr soy sauce, evaluate its flavor characteristic variations.Its
In, soy sauce is commercially available extra large day Gold Label soy.7 males and 9 female for having sensory evaluation experience by 30-41 Sui are tested in sensory evaluation
Property composition.Analyses Methods for Sensory Evaluation Results shows, thinks to add 0.025% γ-Glu- γ-Glu- more than 80% sensory evaluation group member
γ-Glu-Tyr soy sauce, its savoury, which has, to be significantly improved.
Embodiment 3
0.025g and 0.04g γ-Glu- γ-Glu- γ-Glu-Tyr, and 0.5g salt and 0.3g monosodium glutamates are weighed, it is molten
Solution carries out sensory evaluation in 100g water, and with blank sample (0.5g salt is dissolved in 100g water).Sensory evaluation is tested by 30-41
Year is made up of 7 males and 9 women of sensory evaluation experience, and Analyses Methods for Sensory Evaluation Results is shown in Table 1.
From table 1, threshold values of the γ-Glu- γ-Glu- γ-Glu-Tyr in saline solution is respectively 0.04g/100g, is added
Plus monosodium glutamate can obviously reduce γ-Glu- γ-Glu- γ-Glu-Tyr stimulation be in taste threshold value, be 0.025g/100g.
Table 1
Have in 16 sensory evaluation groups 13 people find addition γ-Glu- γ in 0.5% salt and 0.3% monosodium glutamate solution-
Glu- γ-Glu-Tyr sample has significant savoury enhancing effect, and 3 people think that savoury slightly has enhancing.
Embodiment 4
Fresh Grade Breast is mixed with 10 times of weight deionized waters, 100 DEG C are boiled after 30min, filtering remove insoluble substance and
After grease, the salt for adding chicken soup weight 0.3%, the γ-Glu- γ-Glu- of chicken soup weight 0.04% and 0.06% are added respectively
γ-Glu-Tyr, and transfer to sensory evaluation group to evaluate the savoury of chicken soup, it the results are shown in Table 2.Sensory evaluation is tested by 30-
It is made up of 11 males and 9 women of sensory evaluation experience within 41 years old.
Table 2
γ-Glu- γ-Glu- γ-the Glu-Tyr of addition 0.025% and 0.04% in table 2, chicken soup, it is most of
Sensory evaluation member thinks that the savoury of chicken soup has significantly or is increased slightly.
Claims (8)
1. a kind of oligopeptides, it is characterised in that its amino acid sequence is γ-Glu- γ-Glu- γ-Glu-Tyr.
2. dense taste imparting agent, it is characterised in that combined as oligopeptides described in claim 1 and more than one following peptide：
γ-Glu-X-Gly、γ-Glu-Val-Y、γ-Glu-Abu、γ-Glu-Ala、γ-Glu-Gly、γ-Glu-Cys、γ-Glu-
Met、γ-Glu-Thr、γ-Glu-Val、γ-Glu-Orn、Asp-Gly、Cys-Gly、Cys-Met、Glu-Cys、Gly-Cys、
Leu-Asp、D-Cys、γ-Glu-Met(O)、γ-Glu-γ-Glu-Val、γ-Glu-Val-NH2、γ-Glu-Val-ol、
γ-Glu-Ser、γ-Glu-Tau、γ-Glu-Cys(S-Me)(O)、γ-Glu-Leu、γ-Glu-Ile、γ-Glu-t-Leu
With γ-Glu-Cys (S-Me)；X, Y represent amino acid or amino acid derivativges.
3. a kind of flavoring containing oligopeptides described in claim 1, it is characterised in that the γ-Glu- containing more than 330mg/kg
γ-Glu-γ-Glu-Tyr。
4. a kind of flavoring containing dense taste imparting agent described in claim 2, it is characterised in that containing more than 330mg/kg
γ-Glu-γ-Glu-γ-Glu-Tyr。
5. the flavoring according to claim 3 or 4, it is characterised in that the γ-Glu- γ containing more than 1000mg/kg-
Glu-γ-Glu-Tyr。
6. the preparation method of oligopeptides described in claim 1, it is characterised in that glutamine and free tyrosine, mol ratio are 1-2:
1, soluble in water to obtain solution, regulation reaction pH is 7.0-10.0, addition glutaminase or gamma-glutamyl amine transpeptidase 0.02-
1%（w/w）, reacted 3-12 hours at 25-50 DEG C, between the rear pH to 7 ~ 8 with 4 mol/L hydrochloric acid readjustment, 90 DEG C of min of enzyme 10 that go out,
Obtain the reaction solution rich in γ-Glu- γ-Glu- γ-Glu-Tyr.
7. the preparation method of oligopeptides according to claim 6, it is characterised in that：Using 5 μm of 4.6x of XSelect HSS T3
250mm analytical columns, mobile phase A liquid is 0.1%（V/V）Formic acid-the aqueous solution；Mobile phase B liquid is 0.1% (V/V) formic acid-second
Nitrile solution, column temperature is 40 DEG C, and flow velocity is 1 mL/min, the μ L of sample size 10 of reaction solution, using high performance liquid chromatography to reaction
Liquid carries out gradient elution, and appearance time is oligopeptides γ-Glu- γ-Glu- γ-Glu-Tyr for 5.530min peak.
8. preparation method according to claim 6, it is characterised in that the concentration of the solution GLN is 400-
1000mmol/L。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710511184.1A CN107226835A (en) | 2017-06-29 | 2017-06-29 | Savoury peptide, dense taste imparting agent and its flavoring and preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710511184.1A CN107226835A (en) | 2017-06-29 | 2017-06-29 | Savoury peptide, dense taste imparting agent and its flavoring and preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107226835A true CN107226835A (en) | 2017-10-03 |
Family
ID=59936209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710511184.1A Pending CN107226835A (en) | 2017-06-29 | 2017-06-29 | Savoury peptide, dense taste imparting agent and its flavoring and preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107226835A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109566852A (en) * | 2018-11-27 | 2019-04-05 | 宁夏春升源生物科技有限公司 | A kind of alcohol savoury flavor peptide and the preparation method and application thereof |
| CN110484582A (en) * | 2019-08-10 | 2019-11-22 | 珠海佳霖食品有限公司 | Savoury peptide and preparation method thereof in soy sauce |
| WO2022177418A1 (en) * | 2021-02-22 | 2022-08-25 | 경상국립대학교산학협력단 | Umami-enhancing composition containing tyrosine-amino acid peptide, and uses thereof |
| US11659854B2 (en) | 2017-07-13 | 2023-05-30 | Fuji Oil Holdings Inc. | Method for imparting body taste to food |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999746A (en) * | 2006-12-19 | 2007-07-18 | 南京工业大学 | Method for synthesizing gamma-D-glutamyl-L-tryptophan by enzyme method |
| CN102481006A (en) * | 2009-04-01 | 2012-05-30 | 味之素株式会社 | Use of peptide for imparting body taste |
-
2017
- 2017-06-29 CN CN201710511184.1A patent/CN107226835A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100999746A (en) * | 2006-12-19 | 2007-07-18 | 南京工业大学 | Method for synthesizing gamma-D-glutamyl-L-tryptophan by enzyme method |
| CN102481006A (en) * | 2009-04-01 | 2012-05-30 | 味之素株式会社 | Use of peptide for imparting body taste |
Non-Patent Citations (6)
| Title |
|---|
| CARLO F. MORELLI 等: "pH-Dependent hydrolase, glutaminase, transpeptidase and autotranspeptidase activities of Bacillus subtilis γ-glutamyltransferase", 《FEBS JOURNAL》 * |
| H. SUZUKI 等: "g-Glutamyl compounds and their enzymatic production using bacterial g-glutamyltranspeptidase", 《AMINO ACIDS》 * |
| JIANBIN LIU 等: "Discovery of kokumi peptide fromyeast extract by LC-Q-TOF-MS/MS and sensomics approach", 《J SCI FOOD AGRIC》 * |
| RENU NANDAKUMAR等: "Microbial glutaminase: biochemistry, molecular approaches and applications in the food industry", 《JOURNAL OF MOLECULAR CATALYSIS B: ENZYMATIC》 * |
| 姚玉静 等: "γ-谷氨酰肽呈味特性、鉴定及制备方法研究进展", 《中国调味品》 * |
| 崔春 等: "谷朊粉发酵液中鲜味肽的分离、鉴定与呈味分析", 《现代食品科技》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11659854B2 (en) | 2017-07-13 | 2023-05-30 | Fuji Oil Holdings Inc. | Method for imparting body taste to food |
| CN109566852A (en) * | 2018-11-27 | 2019-04-05 | 宁夏春升源生物科技有限公司 | A kind of alcohol savoury flavor peptide and the preparation method and application thereof |
| CN109566852B (en) * | 2018-11-27 | 2022-11-18 | 春发生物科技(宁夏)有限公司 | Mellow taste peptide and preparation method and application thereof |
| CN110484582A (en) * | 2019-08-10 | 2019-11-22 | 珠海佳霖食品有限公司 | Savoury peptide and preparation method thereof in soy sauce |
| WO2022177418A1 (en) * | 2021-02-22 | 2022-08-25 | 경상국립대학교산학협력단 | Umami-enhancing composition containing tyrosine-amino acid peptide, and uses thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107226835A (en) | Savoury peptide, dense taste imparting agent and its flavoring and preparation method | |
| CN107114752A (en) | Savoury peptide, dense taste imparting agent, flavoring and preparation method thereof | |
| CN101600362B (en) | Sweet-type seasoning compositions containing high proportion of amino acid and yeast for obtaining the same | |
| CN102396688B (en) | Flavor-developing active peptide and preparation method and application thereof | |
| EP2380901B1 (en) | Angiotensin converting enzyme inhibitory peptide | |
| US8703223B2 (en) | Natural flavour enhancers from Allium | |
| CN110663931B (en) | Seasoning salt capable of increasing freshness and reducing sodium and preparation method of seasoning salt | |
| JPH1169953A (en) | Production of flavor extract | |
| Huang et al. | Nonvolatile taste components of fruit bodies and mycelia of Cordyceps militaris | |
| CN108024548A (en) | Flavor material from yeast cell wall | |
| CN105886578A (en) | Method for preparing IMP fermented broth or glutamic acid fermented broth used as raw materials for preparing natural neutral flavor | |
| CN106544381A (en) | The preparation method and application of γ glutamy dipeptides | |
| CN107312067A (en) | Oligopeptides γ Glu γ Glu Ile, dense taste imparting agent, flavoring and preparation method thereof | |
| CN107411023A (en) | Savoury peptide, dense taste imparting agent, flavoring and preparation method thereof | |
| Lateef et al. | Estimation of monosodium glutamate by modified HPLC method in various Pakistani spices formula | |
| EP4268615A1 (en) | Non-meat-derived yeast extracts having rich meat flavor and preparation method therefor | |
| CN107226837A (en) | Oligopeptides γ Glu γ Glu Tyr, dense taste imparting agent, flavoring and preparation method thereof | |
| CN107226838A (en) | Oligopeptides γ Glu γ Glu γ Glu Ile, dense taste imparting agent, flavoring and preparation method thereof | |
| EP2298085B1 (en) | Peptide-containing seasoning | |
| CN107118258A (en) | Oligopeptides, dense taste imparting agent, flavoring and preparation method and application | |
| CN107459555A (en) | Oligopeptides, dense taste imparting agent, flavoring and preparation method and application | |
| CN108794573A (en) | A kind of sweet taste peptide and the preparation method and application thereof | |
| CN108634280B (en) | Delicious hexapeptide and application thereof | |
| CN106901311A (en) | Flavor peptide and application | |
| CN108715597A (en) | Sweet taste peptide γ-L-Glu-D-Val and the preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20171003 |
|
| RJ01 | Rejection of invention patent application after publication |