CN107411023A - Savoury peptide, dense taste imparting agent, flavoring and preparation method thereof - Google Patents

Savoury peptide, dense taste imparting agent, flavoring and preparation method thereof Download PDF

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CN107411023A
CN107411023A CN201710211752.6A CN201710211752A CN107411023A CN 107411023 A CN107411023 A CN 107411023A CN 201710211752 A CN201710211752 A CN 201710211752A CN 107411023 A CN107411023 A CN 107411023A
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glu
val
cys
solution
acid
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崔春
相欢
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South China University of Technology SCUT
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Abstract

The invention discloses savoury peptide, dense taste imparting agent, flavoring and preparation method thereof.This γ glutamine peptides(γ‑Glu‑γ‑Glu‑γ‑Glu‑Val)With good stability, the savoury of food particularly flavouring is remarkably improved under 20 100mg/kg concentration.Specifically preparation process is:It is soluble in water after glutamine is mixed with valine, add solution quality 0.001 0.4%(w/w)Glutaminase or γ-glutamate transpeptidase, the pH to 8.0 10.0 of solution is adjusted with 10 mol/l sodium hydroxide solution, is reacted 3 12 hours at 25 50 DEG C, afterwards between 4 mol/L hydrochloric acid readjustment pH to 6 ~ 7,90 DEG C of min of enzyme deactivation 10.

Description

Savoury peptide, dense taste imparting agent, flavoring and preparation method thereof
Technical field
The present invention relates to peptide with flavor effect and preparation method thereof, and in particular to has the γ-Glutamyl Peptide of savoury And preparation method thereof.
Background technology
γ-Glutamyl Peptide deposit extensively with a variety of animals and plants and fermented food, be a kind of safety is natural, the food of safety 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 metabolic activity and the physiological function of γ-Glutamyl Peptide and organism are relevant, 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 has excellent stability, can simplicity and produce at low cost The material for being capable of imparting body taste, there is provided the dense taste imparting agent comprising the material, and with other there is CaSR to swash the material The combinations of substances of dynamic agent activity uses the compound dense taste imparting agent formed.Include γ-Glu-Abu (L- gamma-glutamyl-L-2- ammonia Base butyric acid) dense taste imparting agent, and the material with other have CaSR agonist activities combinations of substances use form 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 acts 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 Kind taste, dramatically increase dense sense (kokumi);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-Val 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 utilizes 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 savoury peptide, its amino acid sequence are γ-Glu- γ-Glu- γ-Glu-Val.
A kind of dense taste imparting agent, it 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, its contain more than 500 weight mg/kg γ-Glu- γ-Glu- γ- Glu-Val。
A kind of flavoring containing the oligopeptides, its contain more than 1500 weight mg/kg γ-Glu- γ-Glu- γ- Glu-Val。
The application of described flavoring, it is specifically:Added in raw-food material outside the flavoring, also add glutamic acid, breast At least one of acid, citric acid, malic acid and butanedioic acid organic acid or its salt make it in food added to raw-food material Concentration be 0.005~0.1 weight %.
The method for preparing a kind of savoury peptide, it is specifically glutamine and free valine, mol ratio 1-2:1, it is molten Yu Shuizhong obtains solution, and regulation reaction pH is 8.0-10.0, and it is solution quality to add glutaminase or gamma-glutamyl amine transpeptidase 0.02-1% (w/w), reacted 3-12 hours at 25-50 DEG C, between using 4mol/L hydrochloric acid readjustment pH to 6~7 afterwards, 90 DEG C of enzyme deactivations 10min, obtain oligopeptides γ-Glu- γ-Glu- γ-Glu-Val.Using 5 μm of 4.6x250mm analyses of XSelect HSS T3 Post, mobile phase A liquid are 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 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, the 6 peaks are oligopeptides γ-Glu- γ-Glu- γ-Glu-Val.
Further, the concentration of solution GLN and free valine is in 400-1000mmol/L.
The present invention compared with prior art, has the following advantages that:
1) present invention firstly discloses γ-Glu- γ-Glu- γ-Glu-Val to have savoury characteristic.
2) make public for the first time and utilize glutaminase or gamma-glutamyl amine transpeptidase catalytic preparation of gamma-Glu- γ-Glu- γ-Glu-Val。
Brief description of the drawings
Fig. 1 is the disparity map that valine adds the no flavor characteristic of enzyme with glutamine mixture;
Fig. 2 is the liquid chromatogram of mixture after reaction;
Fig. 3 is γ-Glu- γ-Glu- γ-Glu-Val level mass spectrogram;
Fig. 4 is γ-Glu- γ-Glu- γ-Glu-Val flavor specificity analysis figure;
Fig. 5 is respectively flavor improvement comparison diagrams of the γ-Glu- γ-Glu- γ-Glu-Val to soy sauce.
Embodiment
Specifically implement to make further citing, but implementation of the invention and guarantor to the present invention below in conjunction with accompanying drawing and example Protect not limited to this.
Embodiment 1
300mM glutamine and 300mM valines are dissolved in 100g water, the pH value of solution is adjusted to 10.0, adds 0.4g glutaminases (Japanese Tian Ye Co., Ltd., vigor 100GTU/g), react 12h respectively at 37 DEG C, after use 4mol/L After hydrochloric acid readjustment pH to 7.0,90 DEG C of enzyme deactivation 10min, sensory evaluation is carried out to product flavor characteristic, flavor characteristic before and after it reacts Such as Fig. 1.
As seen from Figure 1, after reaction terminates, savoury, delicate flavour and the saline taste of reaction solution all significantly improve.
HPLC liquid phases carry out quantitative analysis to reaction product:Analytical column:XSelect HSS T3 5μm 4.6x 250mm; Mobile phase:A liquid:0.1% (V/V) formic acid-aqueous solution;B liquid:0.1% (V/V) formic acid-acetonitrile solution;Column temperature:40 DEG C, flow velocity: 1mL/min.The μ L of sample size 10.Its liquid chromatogram is shown in Fig. 2.It is as shown in table 2 that mobile phase carries out graded.
Table 2
Time/min 0 5 10 15 20
A/% 90 85 20 90 90
In Fig. 2, appearance time is that peak 6 corresponding to 5.478 is γ-glu- γ-glu- γ-glu-val, and peak 6 is received Collection, freeze-drying obtains γ-glu- γ-glu- γ-glu-val, and carries out sensory evaluation.
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(2.1x 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. 3 are carried out to peak 6.From the figure 3, it may be seen that Its primary structure is γ-glu- γ-glu- γ-glu-val.
0.01g γ-glu- γ-glu- γ-glu-val, and 0.5g salt and 0.3g monosodium glutamates are weighed, is dissolved in 100g water In, and carry out sensory evaluation with blank sample (0.5g salt and 0.3g monosodium glutamates are 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 Fig. 4.
From fig. 4, it can be seen that addition 0.01g γ-glu- γ-glu- γ-glu-val sample is compared with the control, solution it is fresh Taste and saline taste significantly improve.
Embodiment 2
Add in 0.01% (g/g) γ-glu- γ-glu- γ-glu-val soy sauce, evaluate its flavor characteristic variations.Its In, soy sauce is commercially available extra large day Gold Label soy.Sensory evaluation is tested by 30-41 year 7 males and 9 female for having sensory evaluation experience Property composition, Analyses Methods for Sensory Evaluation Results such as Fig. 5.As seen from Figure 5,0.01g% γ-glu- γ-glu- γ-glu-val soy sauce is added, Its delicate flavour, savoury, which are respectively provided with, to be significantly improved.
From table 3, γ-glu- γ-glu- γ-glu-val and lactic acid have stronger flavor interaction, add monosodium glutamate The stimulation that both γ-glu- γ-glu- γ-glu-val are can obviously reduce with lactic acid is in taste threshold value.
Table 3
a:Tart flavour (mg/L), b:Savoury solution ph is transferred to 6.5
Embodiment 3
By bacillus amyloliquefaciens (Bacillus amyloliquefaciens) SWJS22 (Chinese microorganism strain preservations Administration committee's common micro-organisms center, deposit number CGMCCNo.8425) fermentation medium is inoculated in 1% inoculum concentration (composition of fermentation medium is: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, supernatant, i.e. glutaminase crude enzyme liquid are filtered to obtain.
600mM glutamine and 300mM valines are dissolved in 100g water, the pH value of solution is adjusted respectively to 9.0, adds 1g crude enzyme liquids, after 40 DEG C are reacted 12h respectively, after adjusting back pH to 7.0 with 4mol/L hydrochloric acid, 90 DEG C of enzyme deactivation 10min, contained γ-glu- γ-glu- γ-glu-val reaction solution.Using 5 μm of 4.6x 250mm analytical columns of XSelect HSS T3, flowing 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, stream Speed is 1mL/min, the μ L of sample size 10 of reaction solution, carries out gradient elution to reaction solution using high performance liquid chromatography, the 6th peak is For oligopeptides γ-Glu- γ-Glu- γ-Glu-Val.
Embodiment 4
With 1% inoculum concentration Bacillus subtillis ATCC 6633 is inoculated in into fermentation medium, and (fermentation medium forms 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 400mM valines are dissolved in 100g water, the pH value of solution is adjusted respectively to 8.0, adds 1g gamma-glutamyl amine transpeptidase crude enzyme liquids, after 40 DEG C are reacted 6h respectively, after adjusting back pH to 7.0 with 4mol/L hydrochloric acid, 90 DEG C go out Enzyme 10min, obtain the reaction solution containing γ-Glu- γ-Glu- γ-Glu- γ-Glu-Val.Using XSelect HSS T35 μm 4.6x 250mm analytical columns, mobile phase A liquid are 0.1% (V/V) formic acid-aqueous solution;Mobile phase B liquid be 0.1% (V/V) formic acid- Acetonitrile solution, column temperature are 40 DEG C, flow velocity 1mL/min, the μ L of sample size 10 of reaction solution, using high performance liquid chromatography to reaction solution Gradient elution is carried out, the 6th peak is oligopeptides γ-Glu- γ-Glu- γ-Glu-Val.

Claims (8)

1. a kind of savoury peptide, it is characterised in that amino acid sequence is γ-Glu- γ-Glu- γ-Glu-Val.
A kind of 2. dense taste imparting agent, it is characterised in that oligopeptides and more than one following peptide described in claim 1 combine and Into: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 and γ-Glu-Cys (S-Me);X, Y represents amino acid or amino acid derivativges.
A kind of 3. flavoring containing oligopeptides described in claim 1, it is characterised in that the γ containing more than 500 weight mg/kg- Glu-γ-Glu-γ-Glu-Val。
4. flavoring according to claim 3, it is characterised in that the γ-Glu- γ containing more than 1500 weight mg/kg- Glu-γ-Glu-Val。
5. the application of the flavoring described in claim 3, it is characterised in that add outside the flavoring in raw-food material, also add At least one of glutamic acid, lactic acid, citric acid, malic acid and butanedioic acid organic acid or its salt make it added to raw-food material Concentration in food is 0.005~0.1 weight %.
6. prepare a kind of method of savoury peptide described in claim 1, it is characterised in that glutamine and free valine, mole Than for 1-2:1, soluble in water to obtain solution, regulation reaction pH is 8.0-10.0, adds glutaminase or gamma-glutamyl amine turns peptide Enzyme is solution quality 0.02-1%(w/w), 25-50 DEG C react 3-12 hours, afterwards with 4 mol/L hydrochloric acid readjustment pH to 6 ~ 7 it Between, 90 DEG C of min of enzyme deactivation 10, obtain-Glu- γ-Glu- the γ of γ containing oligopeptides-Glu-Val reaction solution.
7. preparation method 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 are 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 are 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 the 6th peak is oligopeptides γ-Glu- γ-Glu- γ-Glu-Val.
8. preparation method according to claim 6, it is characterised in that the concentration of solution GLN and free valine In 400-1000mmol/L.
CN201710211752.6A 2017-04-01 2017-04-01 Savoury peptide, dense taste imparting agent, flavoring and preparation method thereof Pending CN107411023A (en)

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CN110477354A (en) * 2019-08-10 2019-11-22 珠海佳霖食品有限公司 The preparation method and application of savoury peptide in soy sauce
US11659854B2 (en) 2017-07-13 2023-05-30 Fuji Oil Holdings Inc. Method for imparting body taste to food

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Cited By (2)

* Cited by examiner, † Cited by third party
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
CN110477354A (en) * 2019-08-10 2019-11-22 珠海佳霖食品有限公司 The preparation method and application of savoury peptide in soy sauce

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