CN103864899A - Polypeptide capable of increasing saline taste, preparation method thereof and salt containing polypeptide - Google Patents
Polypeptide capable of increasing saline taste, preparation method thereof and salt containing polypeptide Download PDFInfo
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- CN103864899A CN103864899A CN201410140312.2A CN201410140312A CN103864899A CN 103864899 A CN103864899 A CN 103864899A CN 201410140312 A CN201410140312 A CN 201410140312A CN 103864899 A CN103864899 A CN 103864899A
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- Prior art keywords
- polypeptide
- fluorenylmethyloxycarbonyl
- amino
- nyl
- salt
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- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 67
- 229920001184 polypeptide Polymers 0.000 title claims abstract description 51
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract description 51
- 150000003839 salts Chemical class 0.000 title claims abstract description 42
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 title claims abstract description 39
- 239000011780 sodium chloride Substances 0.000 title claims abstract description 36
- 235000019640 taste Nutrition 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 241000287828 Gallus gallus Species 0.000 claims description 26
- 235000013330 chicken meat Nutrition 0.000 claims description 26
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 22
- 229960002989 glutamic acid Drugs 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 229920005989 resin Polymers 0.000 claims description 20
- 229940024606 amino acid Drugs 0.000 claims description 17
- 235000001014 amino acid Nutrition 0.000 claims description 17
- 150000001413 amino acids Chemical class 0.000 claims description 17
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000007790 solid phase Substances 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 239000004471 Glycine Substances 0.000 claims description 8
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 6
- 235000013922 glutamic acid Nutrition 0.000 claims description 6
- 239000004220 glutamic acid Substances 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- DDCPKNYKNWXULB-YFKPBYRVSA-N (2s)-2-azaniumyl-3-[(2-methylpropan-2-yl)oxy]propanoate Chemical compound CC(C)(C)OC[C@H]([NH3+])C([O-])=O DDCPKNYKNWXULB-YFKPBYRVSA-N 0.000 claims description 3
- OKKGTZAYJBBICW-UHFFFAOYSA-N 2-(9h-fluoren-1-ylmethoxycarbonylamino)acetic acid Chemical compound C1C2=CC=CC=C2C2=C1C(COC(=O)NCC(=O)O)=CC=C2 OKKGTZAYJBBICW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003875 Wang resin Substances 0.000 claims description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 235000002639 sodium chloride Nutrition 0.000 abstract description 71
- 235000019658 bitter taste Nutrition 0.000 abstract description 4
- 230000036541 health Effects 0.000 abstract description 4
- 108010052164 Sodium Channels Proteins 0.000 abstract description 3
- 102000018674 Sodium Channels Human genes 0.000 abstract description 3
- 230000008447 perception Effects 0.000 abstract description 3
- 231100000716 Acceptable daily intake Toxicity 0.000 abstract 1
- 241001397173 Kali <angiosperm> Species 0.000 abstract 1
- 230000008092 positive effect Effects 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 230000009467 reduction Effects 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000014347 soups Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- 235000008446 instant noodles Nutrition 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000015598 salt intake Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000013923 monosodium glutamate Nutrition 0.000 description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000012549 training Methods 0.000 description 2
- YBONBWJSFMTXLE-UHFFFAOYSA-N 2,3-dichlorobenzoyl chloride Chemical class ClC(=O)C1=CC=CC(Cl)=C1Cl YBONBWJSFMTXLE-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 102000004860 Dipeptidases Human genes 0.000 description 1
- 108090001081 Dipeptidases Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 102100035679 Inositol monophosphatase 1 Human genes 0.000 description 1
- 101710150697 Inositol monophosphatase 1 Proteins 0.000 description 1
- 229920002774 Maltodextrin Polymers 0.000 description 1
- 239000005913 Maltodextrin Substances 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 241000237509 Patinopecten sp. Species 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 235000013614 black pepper Nutrition 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229960002713 calcium chloride Drugs 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 1
- 239000001527 calcium lactate Substances 0.000 description 1
- 235000011086 calcium lactate Nutrition 0.000 description 1
- 229960002401 calcium lactate Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 235000004280 healthy diet Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229960002337 magnesium chloride Drugs 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229940035034 maltodextrin Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000001931 piper nigrum l. white Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 description 1
- 239000001521 potassium lactate Substances 0.000 description 1
- 235000011085 potassium lactate Nutrition 0.000 description 1
- 229960001304 potassium lactate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000020637 scallop Nutrition 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Coloring Foods And Improving Nutritive Qualities (AREA)
- Peptides Or Proteins (AREA)
Abstract
The invention relates to a natural synthetic polypeptide capable of increasing saline taste, a preparation method thereof and a table salt containing the polypeptide, and discloses a molecular structure of the polypeptide capable of increasing saline taste, a preparation method of the polypeptide and a table salt containing the polypeptide. The polypeptide invention has the positive effects that the polypeptide provided by the invention has no bitter taste, like kali salt, and also has no saline taste; the perception of people to saline taste can be enhanced just by improving sensibility of sodium ion channels, the sodium chloride acceptable daily intake of people in life can be effectively reduced, and thus, influence on health of people caused by excessive intake is avoided. The preparation method provided by the invention is simple.
Description
Technical field
The present invention relates to a kind of natural synthetics, particularly relate to a kind of natural synthetic possessing and increase polypeptide of salty function and preparation method thereof and the salt that contains this polypeptide.
Background technology
Salt (sodium-chlor) is requisite added ingredients in food-processing, and the physiological function of human body is also had to material impact.But excessive salt is taken in the generation that can induce a series of diseases, serious threat people's health.The at present harm of verified excessive absorption salt has a lot, wherein most often hypertension, cardiovascular disorder and apoplexy.The edible salt intake of mankind's psychological need every day should be less than 0.25 gram, and the World Health Organization's suitable intake of suggestion adult's salt is 5 grams of every days, and northern China crowd's edible salt intake reaches 12-18 gram/day, is more than World Health Organization's recommended value obtains twice.Along with socio-economic development, standard of living improves constantly, and people more and more focus on healthy diet, thereby overall reduction edible salt intake is extremely urgent.
Instantly the measure that subtracts salt is mainly common salt substitute.Because sylvite, calcium salt, magnesium salts etc. have the physico-chemical property similar to sodium-chlor, thereby alternative sodium chloride is that research adopts maximum approach at present using non-sodium salt as common salt substitute part.Repone K, magnesium chloride, calcium chloride, potassium lactate, calcium lactate etc. have been widely used in foodstuffs industry, and wherein Repone K/sodium chloride mixing salt is most widely used.But non-sodium salt to replace thing exists the problem of self, as Repone K has bitter taste, in mixing salt, the ratio of Repone K exceedes when a certain amount of, just mixing salt bitter taste can obviously rise and saline taste declines.
Polypeptide is to be formed by connecting by peptide bond by amino acid, is extensively present in food.Except nutritive value, much amino acid and peptide class also have taste.Such as Sodium Glutamate namely chickens' extract there is delicate flavour, aspartame is a kind of dipeptidase derivant, its sweet taste is 200 times of sucrose.If can find a kind of polypeptide that can increase saline taste, can address the above problem rapidly undoubtedly.
Summary of the invention
For addressing the above problem, the invention provides a kind of polypeptide that possesses increase saline taste and preparation method thereof, this polypeptide itself does not have saline taste, but it can improve the susceptibility of sodium-ion channel effectively, strengthens the perception of people to saline taste, thus increase saline taste.
For achieving the above object, the present invention institute is by the following technical solutions:
Possess a polypeptide that increases saline taste, its chemical formula is C
18h
29n
5o
11, its molecular structural formula is:
The molecular weight 491.2 of this polypeptide.
A method of preparing aforementioned polypeptides, comprising:
Step 1: N-fluorenylmethyloxycarbonyl-L-Ala is dissolved in Wang resin, then slough its protecting group N-fluorenylmethyloxycarbonyl, first amino acid alanine of peptide chain C end has just been received on solid phase carrier like this;
Step 2: form peptide bond by reacting with the amino that is connected on the L-Ala on resin again after the activated carboxylic of N-fluorenylmethoxycarb-nyl-nyl O-tert-butyl-L-glutamic acid;
Step 3: slough the protecting group N-fluorenylmethyloxycarbonyl of step 2 Glutamic Acid, second amino acid L-glutamic acid of peptide chain C end has just been received on solid phase carrier like this;
Step 4: form peptide bond by reacting with the amino of the L-glutamic acid on resin again after the activated carboxylic of N-fluorenylmethoxycarb-nyl-nyl O-tert-butyl-Serine;
Step 5: slough the protecting group N-fluorenylmethyloxycarbonyl of the Serine in step 4, the 3rd amino acid serine of peptide chain C end just received on solid phase carrier like this;
Step 6: form peptide bond by reacting with the amino of the Serine on resin again after the activated carboxylic of N-fluorenylmethyloxycarbonyl-glycine;
Step 7: slough the protecting group N-fluorenylmethyloxycarbonyl of step 6 glycine, the 4th amino acid glycine of peptide chain C end just received on solid phase carrier like this;
Step 8: form peptide bond by reacting with the amino of the glycine on resin again after the activated carboxylic of N-fluorenylmethoxycarb-nyl-nyl O-tert-butyl-L-glutamic acid;
Step 9: slough protecting group N-fluorenylmethyloxycarbonyl amino on step 8 Glutamic Acid, the five amino acid L-glutamic acid of peptide chain C end has just been received on solid phase carrier like this;
Step 10: the polypeptide crude product that step 9 is made is purified by liquid phase chromatography, obtains sterling.
A kind of edible salt, comprises sodium-chlor, also comprises aforementioned polypeptides.
As preferred version, in above-mentioned edible salt, the weight percent of polypeptide is 0.05%～0.15%.
As preferred plan, in above-mentioned edible salt, the weight percent of polypeptide is 0.1%.
A kind of chickens' extract, comprises salt, the pure powder of chicken, also comprises aforementioned polypeptides.
As preferred version, in above-mentioned chickens' extract, the weight percent of polypeptide is 0.05%～0.15%.
As preferred plan, in above-mentioned chickens' extract, the weight percent of polypeptide is 0.1%.
Beneficial effect of the present invention is:
1) polypeptide of the present invention belongs to natural synthetics, is free from side effects;
2) polypeptide of the present invention has bitter taste unlike sylvite, there is no saline taste, just, by improving the susceptibility of sodium-ion channel, strengthened the perception of people to saline taste yet, can effectively reduce people's intake to sodium-chlor in life, thereby avoid because too much taking in and affect the healthy of people;
3) polypeptide preparation method of the present invention is simple to operate, cheap for manufacturing cost.
Accompanying drawing explanation
Fig. 1 originally contains this patent polypeptide and does not change comparison diagram containing the salt salinity of this patent polypeptide.
Embodiment
In order to make object of the present invention, technical scheme and advantage clearer, below in conjunction with drawings and Examples, the present invention is further elaborated.Should be appreciated that specific embodiment described herein, only in order to explain the present invention, is not limited to the present invention.
Possess a polypeptide that increases saline taste, its chemical formula is C
18h
29n
5o
11, its molecular structural formula is:
The molecular weight 491.2 of this polypeptide.
Prepare a method for aforementioned polypeptides, preparation method embodiment is:
Step 1: by 50 grams of Wang resins (replacement rate 0.83mmol/g) and 300 milliliters of DMF(N, N dimethyl formamide) mix and at room temperature stir, add the N-fluorenylmethyloxycarbonyl-L-Ala of 25.8 grams and the pyridine of 26.8 milliliters, stir after 15 minutes, drip 23.8 milliliters 2,6 one dichlorobenzoyl chlorides carry out, after dripping, stir again two hours, filter resin, use successively DMF(2 × 300 milliliter) and methyl alcohol (2 × 300 milliliters) wash.
Step 2: slough in step 1 protecting group (N-fluorenylmethyloxycarbonyl) amino on L-Ala; first amino acid (L-Ala) of peptide chain C end has just been received solid phase carrier like this; step (1) gained resin is mixed with 500 milliliters of 20% piperidines/DMF solution; under room temperature, stir 30 minutes; filter; resin is used DMF(2 × 300 milliliter successively) and methyl alcohol (2 × 300 milliliters) wash, ninhydrin reaction detect resin positive.
Step 3: by N-fluorenylmethoxycarb-nyl-nyl O-tert-butyl-L-glutamic acid (53 grams), the abbreviation of I-hydroxybenzotriazole (17.3 grams) and HBTU[2-(7-azo benzotriazole)-tetramethyl-urea phosphofluoric acid ester] 47 grams be dissolved in the DMF of 300 milliliters, step (2) gained resin is added and stirred, add again the diisopropyl ethyl amine of 16.1 grams, under room temperature, stir about 1.5 hours, ninhydrin reaction detects resin positive rear filtration, and resin is used DMF(2 × 300 milliliter successively) and methyl alcohol (2 × 300 milliliters) wash.
Step 4: slough protecting group (N-fluorenylmethyloxycarbonyl) amino on step 3 Glutamic Acid, second amino acid (L-glutamic acid) of peptide chain C end has just been received on solid phase carrier like this, operates identical with step (2).The object of this step is that the carboxyl of the L-glutamic acid in three in is not activated.
Step 5: form peptide bond by reacting with the amino of L-glutamic acid on resin again after N-fluorenylmethoxycarb-nyl-nyl O-tert-butyl-Serine (47.7 grams) activated carboxylic, operate identical with step (3), selected activator is I-hydroxybenzotriazole (17.3 grams), HBTU(47 gram) and the diisopropyl ethyl amine of 16.1 grams.
Step 6: slough in step 5 protecting group (N-fluorenylmethyloxycarbonyl) amino on Serine, the 3rd amino acid (Serine) that peptide chain C holds so has just been received on solid phase carrier, operates identical with step (2).
Step 7: react with the amino of Serine on resin again after N-fluorenylmethyloxycarbonyl-glycine (37 grams) activated carboxylic and form peptide bond, operate identical with step (3), selected activator is I-hydroxybenzotriazole (17.3 grams), HBTU(47 gram) and the diisopropyl ethyl amine of 16.1 grams.
Step 8: slough in step 7 protecting group (N-fluorenylmethyloxycarbonyl) amino on glycine, the 4th amino acid (glycine) that peptide chain C holds so has just been received on solid phase carrier, operates identical with step (2).
Step 9: react with the amino that is connected on the glycine on resin again after N-fluorenylmethoxycarb-nyl-nyl O-tert-butyl-L-glutamic acid (53 grams) activated carboxylic and form peptide bond.Operate identically with step (3), selected activator is I-hydroxybenzotriazole (17.3 grams), HBTU(47 gram) and the diisopropyl ethyl amine of 16.1 grams.
Step 10: slough protecting group (N-fluorenylmethyloxycarbonyl) amino on step 9 Glutamic Acid, the five amino acid (L-glutamic acid) of peptide chain C end has just been received on solid phase carrier like this.Operate identical with step (2).
Step 11: vacuum-drying 12 hours, resin weighs 84.6 grams, resin is added to trifluoroacetic acid/tri isopropyl silane/water=95/3/2(weight ratio of 800 grams) mixture stirring at room temperature 2.5 hours, the clear liquid after filtration is poured 8 liters of cold diethyl ethers into.Leave standstill and after 1 hour, filter collecting precipitation (pentapeptide crude product).
Step 12: crude product EGSEA purifies through preparative liquid chromatography, C18 filler, mobile phase A is that in 1% ethanol, to add 0.1% hydrochloric acid, Mobile phase B be that in 90% ethanol, to add 0.1% hydrochloric acid, linear gradient be 40 minutes B from 0 to 50%.
Step 13: obtain 16 grams of sterlings, C
18h
29n
5o
11, molecular weight 491.2, sterling is white, tasteless.Whole synthetic productive rate is 80%.The purity of product is by nuclear-magnetism, and chromatography-mass spectroscopy is confirmed.
A kind of edible salt, comprises sodium-chlor, also comprises aforementioned polypeptides.
As preferred version, in above-mentioned edible salt, the weight ratio of polypeptide is 0.05%～0.15%.
As preferred plan, in above-mentioned edible salt, the weight ratio of polypeptide is 0.1%
A kind of chickens' extract, comprises salt, the pure powder of chicken, also comprises aforementioned polypeptides.
As preferred version, in above-mentioned chickens' extract, the weight ratio of polypeptide is 0.05%～0.15%.
As preferred plan, in above-mentioned chickens' extract, the weight ratio of polypeptide is 0.1%
Embodiment 1: the function measure experiment of this patent polypeptide (hereinafter to be referred as " EGSEA ")
With 0.1%, 0.2%, 0.3%, 0.4% and 0.5% common salt aqueous solution is made object of reference, 0.1% salt solution salinity is decided to be 5,0.5% salt solution salinities and is decided to be 20, then by the fragrant member of ten product, 0.1% common salt aqueous solution is added to 0.1%EGSEA(weight ratio), 0.2% common salt aqueous solution adds 0.1%EGSEA, and 0.3% common salt aqueous solution adds the saline taste that 0.1%EGSEA and 0.4% common salt aqueous solution add four kinds of mixtures of 0.1%EGSEA and assesses.Test is shown in shown in accompanying drawing 1.Result: 0.2% common salt aqueous solution adds after 0.1%EGSEA, the salinity of solution improves, and approaches the salinity of 0.3% salt solution.0.3% common salt aqueous solution adds after 0.1%EGSEA, and the salinity of solution improves, and approaches the salinity of 0.4% salt solution.0.4% common salt aqueous solution adds after 0.1%EGSEA, and the salinity of solution improves, and exceedes the salinity of 0.5% salt solution.Totally it seems, 0.1% EGSEA has the effect that subtracts salt about 30%.
Embodiment 2:EGSEA is for salt reduction instant noodles
40 ordinary consumer (20 of men; 20 of female; age 18-50 year) participate in the experiment; these tasters were never subject to any training; every human consumer trial test of taking one's seat in separate room when contrast; provide four kinds of sample faces to everyone, be respectively instant noodles, (2) salt reduction 30% of (1) common not salt reduction and add 0.05%EGSEA; (3) salt reduction 30% add 0.1%EGSEA; (4) salt reduction 30% add 0.5%EGSEA.Require them to give a mark in acceptance level to four kinds of faces, 1 point minimum, and 10 points the highest.Result overwhelming majority human consumers can not differentiate salt reduction 30% and add the instant noodles of 0.1%EGSEA and the difference of salt reduction instant noodles in mouthfeel and saline taste not.
| Sample | Consumers' Acceptance |
| Not salt reduction | 8.0 |
| Salt reduction 30% adds 0.05%EGSEA | 6.2 |
| Salt reduction 30% adds 0.1%EGSEA | 8.1 |
| Salt reduction 30% adds 0.15%EGSEA | 8.3 |
Embodiment 3:EGSEA is for salt reduction chickens' extract
40 ordinary consumer (20 of men, 20 of female, age 18-50 year) participate in the experiment, these tasters were never subject to any training, every human consumer trial test of taking one's seat in separate room when contrast, providing two kinds of sample chickens' extract soup to everyone, is respectively chickens' extract soup, (2) salt reduction 30% of (1) common not salt reduction the chickens' extract soup that adds 0.1%EGSEA.Require them to compare in acceptance level two kinds of soup, result overwhelming majority human consumer can not differentiate the difference of two kinds of chickens' extract soup in mouthfeel and saline taste.
| Material name and specification | The common salt chickens' extract proportioning that do not subtract | Subtract salt 30% chickens' extract proportioning |
| Salt | 31 | 21.7, add 0.1EGSEA, add 9.2 starch |
| Sugar | 6.5 | 6.5 |
| MSG | 40 | 40 |
| I+G | 2 | 2 |
| Dried scallop powder | 0.8 | 0.8 |
| IMP | 1 | 1 |
| The pure powder of chicken | 3 | 3 |
| Chicken essence | 2 | 2 |
| Maltodextrin | 4.3 | 4.3 |
| White pepper powder | 0.4 | 0.4 |
| Onion powder | 0.5 | 0.5 |
| Ginger powder | 0.2 | 0.2 |
| Yeastex | 2 | 2 |
| M-M100 | 2 | 2 |
| Chicken fat essence | 0.3 | 0.3 |
| Chicken fat | 2 | 2 |
| Citric acid | 12ppn | 12ppn |
| Antioxidant | 0.002 | 0.002 |
| Anticaking agent | 1 | 1 |
| Amount to | 100 | 100 |
Embodiment 4
The difference of the present embodiment and embodiment 3 is only that in chickens' extract, the proportioning of EGSEA and starch is respectively 0.15 and 9.15.
Embodiment 5
The difference of the present embodiment and embodiment 3 is only that in chickens' extract, the proportioning of EGSEA and starch is respectively 0.05 and 9.25.
Claims (8)
1. possess a polypeptide that increases saline taste, its chemical formula is C
18h
29n
5o
11, its molecular structural formula is:
2. a preparation method who prepares claim 1 polypeptide, comprising:
Step 1: N-fluorenylmethyloxycarbonyl-L-Ala is dissolved in Wang resin, then slough its protecting group N-fluorenylmethyloxycarbonyl, first amino acid of peptide chain C end has just been received on solid phase carrier like this;
Step 2: form peptide bond by reacting with the amino that is connected on the L-Ala on resin again after the activated carboxylic of N-fluorenylmethoxycarb-nyl-nyl O-tert-butyl-L-glutamic acid;
Step 3: slough the protecting group N-fluorenylmethyloxycarbonyl of step 2 Glutamic Acid, second amino acid of peptide chain C end has just been received on solid phase carrier like this;
Step 4: form peptide bond by reacting with the amino of the L-glutamic acid on resin again after the activated carboxylic of N-fluorenylmethoxycarb-nyl-nyl O-tert-butyl-Serine;
Step 5: slough the protecting group N-fluorenylmethyloxycarbonyl of the Serine in step 4, the 3rd amino acid of peptide chain C end has just been received on solid phase carrier like this;
Step 6: form peptide bond by reacting with the amino of the Serine on resin again after the activated carboxylic of N-fluorenylmethyloxycarbonyl-glycine;
Step 7: slough the protecting group N-fluorenylmethyloxycarbonyl of step 6 glycine, the 4th amino acid of peptide chain C end has just been received on solid phase carrier like this;
Step 8: form peptide bond by reacting with the amino of the glycine on resin again after the activated carboxylic of N-fluorenylmethoxycarb-nyl-nyl O-tert-butyl-L-glutamic acid;
Step 9: slough protecting group N-fluorenylmethyloxycarbonyl amino on step 8 Glutamic Acid, the five amino acid of peptide chain C end has just been received on solid phase carrier like this;
Step 10: the polypeptide crude product that step 9 is made is purified by liquid phase chromatography, obtains sterling.
3. an edible salt, comprises sodium-chlor, it is characterized in that: also comprise polypeptide claimed in claim 1.
4. edible salt according to claim 3, is characterized in that: the weight percent of described polypeptide is 0.05%～0.15%.
5. edible salt according to claim 4, is characterized in that: the weight percent of described polypeptide is 0.1%.
6. a chickens' extract, comprises salt, the pure powder of chicken, it is characterized in that: also comprise polypeptide claimed in claim 1.
7. chickens' extract according to claim 6, is characterized in that: the weight percent of described polypeptide is 0.05%～0.15%.
8. chickens' extract according to claim 7, is characterized in that: the weight percent of described polypeptide is 0.1%.
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| CN107846947A (en) * | 2015-05-27 | 2018-03-27 | 杜克马塔克有限公司 | Strengthen salt composite and preparation method thereof |
| CN106923298A (en) * | 2017-05-17 | 2017-07-07 | 陈丹燕 | A kind of low-sodium healthcare salt suitable for cardiovascular patient and preparation method thereof |
| CN109007750A (en) * | 2018-06-20 | 2018-12-18 | 陈玉海 | A kind of dedicated low sodium complex peptides salt of the elderly |
| CN109007751A (en) * | 2018-06-20 | 2018-12-18 | 陈玉海 | A kind of low sodium peptide salt |
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Effective date of registration: 20161227 Address after: 436032 Gedian Development Zone, Hubei Province, No. building road, No. 77 Patentee after: Pan o'laughlin (Wuhan) Biological Technology Co. Ltd. Address before: 430067 Hubei Province, Wuhan city Wuchang District Luoshi Road No. 76 building room 2306, vista Patentee before: Lei Guotai |
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Address after: 436070 No. 77 Construction Avenue, Gedian Economic Development Zone, Ezhou City, Hubei Province Patentee after: Pan-Asia (Wuhan) Food Technology Co., Ltd. Address before: 436032 No. 77 Construction Avenue, Gedian Development Zone, Ezhou City, Hubei Province Patentee before: Pan o'laughlin (Wuhan) Biological Technology Co. Ltd. |