CN101580480B - Method for preparing substance-glutamine for increasing immunoregulation of piglet - Google Patents
Method for preparing substance-glutamine for increasing immunoregulation of piglet Download PDFInfo
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- CN101580480B CN101580480B CN2009100436908A CN200910043690A CN101580480B CN 101580480 B CN101580480 B CN 101580480B CN 2009100436908 A CN2009100436908 A CN 2009100436908A CN 200910043690 A CN200910043690 A CN 200910043690A CN 101580480 B CN101580480 B CN 101580480B
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Abstract
The invention discloses a method for preparing a substance-glutamine for increasing the immunoregulation of grice. The steps are as follows: a. L-glutamic acid, methanol and sulphuric acid are mixed to react, and triethylamine is used for regulating the pH value of the mixed liquor to obtain L-gamma-glutamic acid methyl ester; b. the L-gamma-glutamic acid methyl ester obtained in step a is added to the mixed liquor of methanol and carbon bisulfide, ammonia is introduced until saturation, and the gamma-methyl ester-L-glutamic acid-N-dithiocarbamate concentrated solution can be obtained after sealing storage, concentration and ammonia elimination; c. the concentrated solution obtained in step b is heated, the acetic acid is added to the concentrated solution, and the crude product of glutamine can be obtained after carbon bisulfide elimination by decompression; and d. the crude product of glutamine obtained in step c are processed by active carbon decolorization and recrystallization to obtain the finished product. The glutamine prepared by the invention is prepared from the raw material of glutamic acid, and the method has the advantages of simple operation, easy access to raw materials and lower cost. The glutamine prepared by the invention effectively reduces the rate of diarrhea of the grice, and increases the concentration of immunological factors in the blood serum of the grice.
Description
Technical field
The chemosynthesis and this compound that the present invention relates to amino acid amide more specifically relate to a kind of preparation method who improves the substance-glutamine of immunoregulation of grice in piglet immunological regulation technology field.These article can transform hexosamine in animal body, as synthetic mucinous precursor, can promote ulcer healing, promote piglet growth performance.
Background technology
The domestic and international in recent years research report about amino acid and cellular immunization is more, particularly Stimulina and l-arginine.Stimulina has immune-enhancing effect, and its vital role is exactly immunomodulatory.The phagolysis of scavenger cell, lymphopoiesis and protein synthesis all must have competent Stimulina.Ogle etc. (1994) find, add the sterilizing ability that Stimulina can strengthen the burn patient neutrophil leucocyte.Stimulina can prevent the intestinal mucosa atrophy effectively, keeps normal intestinal mucosa weight, structure and protein contnt, and it is active to strengthen intestinal cell, improves the intestine immunity function, reduces intestinal bacteria and endotoxic transposition.Stimulina can be controlled the proliferative effect of immuning tissue and can strengthen its function, and the performance of these effects depends on the concentration of Stimulina, and glutamine concentration is high more, and the immunne response of body is perfect more more by force.
As gsh synthetic precursor, Stimulina is playing an important role aspect removing oxygenant and the adjusting immunne response.Recent study shows, adds an amount of Stimulina in the daily ration and can improve piglet production performance and keep best body condition (Roth et al., 1999) childhood to greatest extent.To being in the animal under the immunoreation state, daily ration adds Stimulina to keeping best immunological status necessary (Parry-Billing etal., 1990).
At present, the production of Stimulina chemical synthesis is arranged, extraction method and utilize three kinds of microbe fermentation methods etc. from plant.From pumpkin, Sunflower Receptacle seedling, extracting can not suitability for industrialized production.Mass production can only adopt chemical synthesis and fermentation method, but the production efficiency of producing Stimulina with microbial fermentation with glucose or acetate is low, and yield has only 39%, and the production cost of chemical synthesis is low, and yield is high.
Summary of the invention
The objective of the invention is to be to provide a kind of preparation method who improves the substance-glutamine of immunoregulation of grice, method is simple, and easy and simple to handle, raw material is easy to get, and cost is lower.These article are raw material with the monosodium glutamate, and raw material is easy to get, and reaction is carried out at normal temperatures and pressures, energy-conserving and environment-protective, and cost is low.It can also play regulating effect to immunity system as nervus centralis and peripheroneural mediator except the energy matter as cellular metabolism.
In order to realize above-mentioned purpose, the present invention adopts following material: L-L-glutamic acid, methyl alcohol, sulfuric acid, triethylamine, dithiocarbonic anhydride, ammoniacal liquor and gac.
A kind of preparation method who improves the substance-glutamine of immunoregulation of grice the steps include:
A. L-L-glutamic acid (0.05-0.30kg), methyl alcohol (3.5-20L), sulfuric acid (0.35-2L) are mixed, room temperature (20-25 ℃, below identical) reaction 2-6h makes the pH of mixed value be adjusted to 7.0-9.5 with triethylamine again, obtains L-gamma-glutamic acid methyl esters;
B. the L-gamma-glutamic acid methyl esters (0.15-0.20kg) that step a is obtained joins in the mixed solution of methyl alcohol (0.35-2L) and dithiocarbonic anhydride (0.35-2L), and feeds ammonia to saturated, 28-40 ℃ airtight, place 38-50h.Concentrate down except that getting γ-methyl esters-L-L-glutamic acid-N-dithiocarbamate liquid concentrator behind the ammonia through 1500～7000Pa pressure condition;
C. the liquid concentrator that step b is obtained is heated to 40-60 ℃, and adding acetic acid to pH value is 6.5-7.5, under 1500～7000Pa pressure condition, removes dithiocarbonic anhydride, obtains the Stimulina bullion;
D. the Stimulina bullion that step c is obtained gets finished product through activated carbon decolorizing, recrystallization, perhaps adopts the ion exchange method condensing crystal to obtain the Stimulina finished product.
The present invention and present compared with techniques have the following advantages and effect:
Present method is produced Stimulina, and the employing monosodium glutamate is a raw material, and raw material is easy to get, and reaction is carried out at normal temperatures and pressures, and method is simple, and easy and simple to handle, raw material is easy to get, energy-conserving and environment-protective, and cost is lower.Applied range except that the fodder additives as piglet, also can be used as the control digestive tract ulcer.This laboratory study shows, the Stimulina of interpolation 0.4% and 0.8% in the daily ration 14 days, and the average daily gain of piglet improves 17.96% and 24.45% respectively; And reduced the grice diarrhoea rate effectively, be reduced to 10.29% and 5.10% respectively by 17.16% of control group.
Embodiment
Embodiment 1:
A kind of preparation method who improves the substance-glutamine of immunoregulation of grice, its step is following:
A. get methyl alcohol 20L, L-glutamic acid 0.30kg adds sulfuric acid 2L and mixes, and room temperature reaction 4h with triethylamine adjust pH to 8.5, gets L-gamma-glutamic acid methyl esters;
B. the L-gamma-glutamic acid methyl esters that step a is obtained is added drop-wise in the mixed solution of 2L methyl alcohol and 2L dithiocarbonic anhydride; Drip on one side; Feed ammonia on one side to saturated; At 32 ℃ of airtight placement 42h, concentrating under the 1500Pa pressure condition except that getting γ-methyl esters-L-L-glutamic acid-N-dithiocarbamic acid two amine salt liquid concentrators behind the ammonia;
C. the liquid concentrator that step b is obtained is heated to 50 ℃, and adding acetic acid to pH value is 6.5, and dithiocarbonic anhydride is removed in decompression under the 2000Pa pressure condition, separates out mass crystallization, i.e. Stimulina bullion this moment;
D. the crystallization of step c gained Stimulina bullion is got the Stimulina finished product through activated carbon decolorizing, recrystallization.
Embodiment 2:
A. get methyl alcohol 15L, L-glutamic acid 0.22kg adds sulfuric acid 1.5L, and room temperature reaction 3h with triethylamine adjust pH to 8.0, gets L-gamma-glutamic acid methyl esters;
B. the L-gamma-glutamic acid methyl esters that step a is obtained is added drop-wise in the mixed solution of 1.5L methyl alcohol and 1.5L dithiocarbonic anhydride; Drip on one side; Feed ammonia on one side to saturated; At 30 ℃ of airtight placement 40h, concentrating under the 2000Pa pressure condition except that getting γ-methyl esters-L-L-glutamic acid-N-dithiocarbamic acid two amine salt liquid concentrators behind the ammonia;
C. the liquid concentrator that step b is obtained is heated to 45 ℃, and adding acetic acid to pH value is 6.8, and dithiocarbonic anhydride is removed in decompression under the 3000Pa pressure condition, separates out mass crystallization, i.e. Stimulina bullion this moment;
D. the crystallization of step c gained Stimulina bullion is got the Stimulina finished product through activated carbon decolorizing, recrystallization.
Embodiment 3:
A. get methyl alcohol 10L, L-L-glutamic acid 0.15kg, sulfuric acid 1L mixing, room temperature reaction 2h with triethylamine adjust pH to 7.5, obtains L-gamma-glutamic acid methyl ester solution;
B. the L-gamma-glutamic acid methyl ester solution that step a is obtained is added drop-wise in the mixed solution of 1L methyl alcohol and 1L dithiocarbonic anhydride, feeds ammonia then to saturated, 29 ℃ airtight, place 39h.Obtain γ-methyl esters-L-L-glutamic acid-N-dithiocarbamate liquid concentrator through concentrating except that behind the ammonia under the 2500Pa pressure condition;
C. the liquid concentrator that step b is obtained is heated to 42 ℃, and adding acetic acid to pH value is 7.0, under the 4000Pa pressure condition, removes dithiocarbonic anhydride, obtains the Stimulina bullion;
D. the Stimulina bullion that step c is obtained gets the Stimulina finished product through activated carbon decolorizing, recrystallization.
Embodiment 4:
A. get methyl alcohol 7L, L-glutamic acid 0.1kg adds sulfuric acid 0.7L, mixes, and room temperature reaction 5h with triethylamine adjust pH to 7.9, gets L-gamma-glutamic acid methyl esters;
B. the L-gamma-glutamic acid methyl esters that step a is obtained is added drop-wise in the mixed solution of 0.7L methyl alcohol and 0.7L dithiocarbonic anhydride; Drip on one side; Feed ammonia on one side to saturated; At 35 ℃ of airtight placement 45h, concentrating under the 3000Pa mercurypressure condition except that getting γ-methyl esters-L-L-glutamic acid-N-dithiocarbamic acid two amine salt liquid concentrators behind the ammonia;
C. the liquid concentrator that step b is obtained is heated to 55 ℃, and adding acetic acid to pH value is 7.2, and dithiocarbonic anhydride is removed in decompression under the 4500Pa pressure condition, separates out mass crystallization, i.e. Stimulina bullion this moment;
D. the Stimulina bullion crystallization that step c is obtained gets the Stimulina finished product through activated carbon decolorizing, recrystallization.
Embodiment 5:
A. get methyl alcohol 3.5L, L-glutamic acid 0.05kg adds sulfuric acid 0.35L, and room temperature reaction 6h adds triethylamine adjust pH to 9.0, gets L-gamma-glutamic acid methyl esters;
B. the L-gamma-glutamic acid methyl esters that step a is obtained is added drop-wise in the mixed solution of 0.35L methyl alcohol and 0.35L dithiocarbonic anhydride; Drip on one side; Feed ammonia on one side to saturated; At 40 ℃ of airtight placement 50h, concentrating under the 4000Pa pressure condition except that getting γ-methyl esters-L-L-glutamic acid-N-dithiocarbamic acid two amine salt liquid concentrators behind the ammonia;
C. the liquid concentrator that step b is obtained is heated to 60 ℃, and adding acetic acid to pH value is 7.5, and dithiocarbonic anhydride is removed in decompression under the 7000Pa pressure condition, separates out mass crystallization, i.e. Stimulina bullion this moment;
D. the Stimulina bullion crystallization that step c is obtained gets the Stimulina finished product through activated carbon decolorizing, recrystallization.
Added 0.4% and 0.8% the Stimulina that makes with present method in the daily ration 14 days, the average daily gain of piglet improves 17.96% and 24.45% respectively; And reduced the grice diarrhoea rate effectively, be reduced to 10.29% and 5.10% respectively by 17.16% of control group.And can improve the concentration of immune factor in the piglet serum (IgA, IgM, IgG, IL-6, IL-I β and IL-2).
Claims (1)
1. a preparation method who improves the substance-glutamine of immunoregulation of grice the steps include:
A. L-L-glutamic acid, methyl alcohol, sulfuric acid are mixed, room temperature reaction 2-6h regulates the pH of mixed value to 7.0-9.5 with triethylamine again, obtains L-gamma-glutamic acid methyl esters;
B. the L-gamma-glutamic acid methyl esters that step (a) is obtained joins in the mixed solution of methyl alcohol and dithiocarbonic anhydride; And feed ammonia to saturated; 28-40 ℃ airtight, place 38-50h, concentrate down through 1500～7000Pa pressure condition and get γ-methyl esters-L-L-glutamic acid-N-dithiocarbamate liquid concentrator after removing ammonia;
C. the liquid concentrator that step (b) is obtained is heated to 40-60 ℃, adds acetic acid, under 1500～7000Pa pressure condition, removes dithiocarbonic anhydride, obtains the Stimulina bullion;
D. the Stimulina bullion that step (c) is obtained gets the Stimulina finished product through activated carbon decolorizing, recrystallization.
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| US20190208800A1 (en) * | 2018-01-05 | 2019-07-11 | The United States Of America, As Represented By The Secretary Of Agriculture | L-glutamine in swine diets |
| CN110373369B (en) * | 2019-06-25 | 2021-06-08 | 华中农业大学 | Recombinant bacillus subtilis engineering bacterium for producing pig glutamine synthetase, construction method and application thereof |
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Non-Patent Citations (2)
| Title |
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| JP平3-112953A 1991.05.14 |
| 池江涛 等.L-谷氨酰胺合成及不对称转化.《化学反应工程与工艺》.2002,第18卷(第2期),第163-167页. * |
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Effective date of registration: 20131018 Address after: 19-20, No. 2, No. 410005, first West Road, Furong West Road, Furong district, Hunan, Changsha Patentee after: Hunan New Wellful Co., Ltd. Address before: 410125 Hunan province Changsha Furong district Mapoling two Yuanda Road No. 1071 Patentee before: Institute of Subtropical Agriculture, Chinese Academy of Sciences |