WO2019144589A1 - Méthode de préparation de tréhalose à teneur élevée - Google Patents

Méthode de préparation de tréhalose à teneur élevée Download PDF

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Publication number
WO2019144589A1
WO2019144589A1 PCT/CN2018/097577 CN2018097577W WO2019144589A1 WO 2019144589 A1 WO2019144589 A1 WO 2019144589A1 CN 2018097577 W CN2018097577 W CN 2018097577W WO 2019144589 A1 WO2019144589 A1 WO 2019144589A1
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liquid
trehalose
crystallization
corn
content
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PCT/CN2018/097577
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English (en)
Chinese (zh)
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伊婷婷
富春丽
齐志伟
李军
范世远
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通辽梅花生物科技有限公司
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Priority to JP2020562807A priority Critical patent/JP7062090B2/ja
Publication of WO2019144589A1 publication Critical patent/WO2019144589A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/24—Preparation of compounds containing saccharide radicals produced by the action of an isomerase, e.g. fructose
    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/12—Disaccharides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/04—Disaccharides
    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y302/00—Hydrolases acting on glycosyl compounds, i.e. glycosylases (3.2)
    • C12Y302/01—Glycosidases, i.e. enzymes hydrolysing O- and S-glycosyl compounds (3.2.1)
    • C12Y302/01141—4-Alpha-D-{(1->4)-alpha-D-glucano} trehalose trehalohydrolase (3.2.1.141)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y504/00—Intramolecular transferases (5.4)
    • C12Y504/99—Intramolecular transferases (5.4) transferring other groups (5.4.99)
    • C12Y504/99015—(1->4)-Alpha-D-glucan 1-alpha-D-glucosylmutase (5.4.99.15)

Definitions

  • the invention relates to a preparation method of trehalose, in particular to a preparation method of high content trehalose.
  • Trehalose also known as leaking sugar, sugar, etc.
  • Trehalose has a magical protective effect on organisms. Under the harsh environmental conditions of high temperature, high cold, high osmotic pressure and dry water loss, trehalose can form a unique protective film on the cell surface, effectively protecting the invariant inactivation of protein molecules. To maintain the life process and biological characteristics of the living body. In nature, other sugars such as sucrose and glucose do not have this function.
  • This unique functional property makes trehalose not only an excellent protective agent for protein drugs, enzymes, vaccines and other biological products, but also an important component for maintaining cell activity and moisturizing cosmetics.
  • the unique food ingredients of fresh food flavor and improved food quality have greatly expanded the function of trehalose as a natural edible sweet candy.
  • trehalose products are mainly used in the fields of baking, medicine, cosmetics, food preservation, etc., mainly to moisturize, lock water, protect color, reduce the Maillard reaction, improve product quality, extend product shelf life, is a An important food.
  • the role of trehalose products depends on the level of trehalose in their products. The higher the trehalose content in the product, the better its functionality. Therefore, it is used in foods and cosmetics with high levels of trehalose.
  • ion exchange desalting and chromatographic separation and purification are generally used, and the prepared trehalose content is about 98%; or the alcoholization separation is used for purification, but some chemical reagents are needed in the alcoholation separation, for example, Alcohols, which have a certain amount of retention in trehalose products, cannot be completely removed.
  • Alcohols which have a certain amount of retention in trehalose products, cannot be completely removed.
  • the content of trehalose in the product is increased, the application range of trehalose products is limited to some extent, such as the retention of alcoholic substances. Trehalose products cannot be used in cosmetics.
  • the object of the present invention is to provide a preparation method of high content trehalose with high trehalose content, high yield and uniform particle size.
  • a high-content trehalose preparation method which comprises the following steps in sequence: (1) preparation of starch milk; (2) liquefaction; (3) double enzymatic hydrolysis; (4) filtration and protein removal; (5) Decolorization; (6) desalting; (7) nanofiltration and chromatographic separation and purification; (8) concentrated crystallization; (9) separation and drying to obtain a finished product.
  • the specific operation steps of the nanofiltration and chromatographic separation and purification are as follows: firstly, the desalting liquid obtained in the previous step is subjected to nanofiltration, and the molecular weight cutoff of the nanofiltration membrane is 200-300 Da, and the quality of the trehalose in the nanofiltrate. The percentage is ⁇ 98%; the nanofiltrate is diluted with purified water to obtain a trehalose concentration of 15-25% in the diluent; the dilution is chromatographically separated, and the chromatographic separation temperature is 65-75 ° C, The purified liquid is obtained, and the mass percentage of trehalose in the purified liquid is ⁇ 99.5%. Purification is carried out by a combination of nanofiltration and chromatographic separation to increase the trehalose content in the product.
  • the specific operation steps of preparing the starch milk are: taking corn into water, the ratio of the corn to the water is 5-8: 2-5, the temperature of the soaking water is 40-60 ° C, soaking to the The seed coat of the corn can be peeled off to obtain the soaked corn; the moisture is filtered off and the soaked corn is crushed until the whole grain amount is ⁇ 10 grains/100 g to obtain the crushed corn; the crushed corn is ground to remove the germ in the corn , the amount of corn germ in the slurry is less than 5 / 100ml, to obtain a slurry; the slurry is disc separated, until the protein content of the slurry is ⁇ 10%, to obtain the starch milk;
  • the specific operation step of the liquefying is: after the preparation of the starch milk, the starch milk is concentrated to 15-30Be to obtain a concentrated starch milk; the concentrated starch milk is liquefied, the liquefaction temperature is 110-120 ° C, and the liquefaction time is 15-25 min, obtaining a liquefied liquid;
  • the specific operation step of the double enzymatic hydrolysis is: after the liquefaction is completed, a complex enzyme is added to the liquefaction liquid, and the mass of the composite enzyme is 5-15% of the mass of the starch milk, and the pH is 4.0-4.5. Enzymatic hydrolysis at a temperature of 48-62 ° C, the enzymatic hydrolysis time is 36-60 h, to obtain an enzymatic hydrolysate;
  • the specific operation step of filtering the protein is as follows: after the double enzymatic hydrolysis is completed, the enzymatic hydrolysate is filtered, the filtration precision is 5-25 ⁇ m, and the filtration is carried out until the translucent value of the filtrate is more than 90%, that is, the deproteinized solution is obtained;
  • the specific operation step of the decolorization is: after the filtration of the protein is completed, the activated carbon particles are added to the deproteinized liquid, and the mass of the activated carbon particles is 0.1-1% of the mass of the filtrate, and the temperature is 65-70 ° C. Decolorization under the conditions of 30-60min, and then cyclic filtration to remove activated carbon particles, until the filtrate transmission value of 98% or more, that is, a decolorizing solution;
  • the specific operation step of the desalination is: after the decolorization is completed, the decolorizing liquid is ion-exchanged, and the conductivity of the ion exchange liquid is less than 50 us/cm, that is, the desalting liquid is obtained;
  • the specific operation step of the concentrated crystallization is as follows: after the purification is completed, the purification liquid is subjected to evaporation crystallization until the mass percentage of trehalose in the evaporation crystallization liquid is ⁇ 60%, and then cooling and crystallization is performed, when the cooling is performed. When the temperature of the crystallization falls below 20 ° C, the cooled crystallization liquid is obtained;
  • the specific operation steps of the separation and drying to obtain the finished product are: after the concentrated crystallization is completed, the cooled crystallization liquid is centrifuged to obtain a wet product; and the wet product is dried to a water content of ⁇ 1% to obtain the high content. Finished trehalose.
  • the cooling crystallization has a cooling rate of 4-6 ° C / h.
  • the complex enzyme includes MThase (malt oligosaccharide-based trehalose hydrolase) and MTsase (malto-oligosaccharide-based trehalose synthase), and the mass ratio of the MThase to the MTsase is 2:1,
  • the activity values of MThase and MTsase were both 1-20 U/g.
  • the trehalose content is calculated according to the calculation formula of trehalose content in the national standard 23529-2009.
  • the invention has the advantages that: the product prepared by the invention has a trehalose content of more than 99.7%, and has good functionality; compared with the ordinary trehalose product, the usage amount of the same effect can be reduced by 2-5%, and the use can be reduced.
  • the cost of the product; good water retention, used for baking can improve the bulkiness of the baked product, and for cosmetics can improve the moisture retention of the cosmetic; can effectively reduce the occurrence of Maillard reaction, and has strong color protection ability for fruits and vegetables; 2.
  • the product of the invention has high yield, close to 100%, can improve the output of the enterprise and is beneficial to industrial production; 3.
  • the product of the invention has a particle size of 30 mesh or less and 70% or more, and the particle size of 40 mesh or less accounts for more than 60%. More than 200% of the above 200 mesh; the particles are more uniform, faster than ordinary trehalose products, easy to use.
  • High-content trehalose preparation method which specifically comprises: (1) starch milk preparation, (2) liquefaction, (3) double enzymatic hydrolysis, (4) filtration to remove protein, (5) decolorization, (6) desalting, (7) Purification, (8) concentrated crystallization, (9) separation and drying;
  • Preparation of starch milk Take corn into water, the ratio of corn to water is 6.6:4.5, the temperature of soaking water is 50 °C, soaked until the seed coat of corn can be peeled off, soaked corn; filter water and soak corn The crushing is carried out to separate the seed coat to a whole grain amount of 5 grains/100 g to obtain crushed corn; the crushed corn is ground to remove the germ in the corn, and the amount of the corn germ in the polishing liquid is 2/100 ml, which is ground. Liquid; the slurry is separated by a disc, and the protein content in the slurry is 6% to obtain starch milk;
  • Double enzymatic hydrolysis (2) After liquefaction is completed, a complex enzyme is added to the liquefaction solution.
  • the complex enzyme includes MThase and MTsase.
  • the mass ratio of MThase to MTsase is 2:1, and the activity of MThase and MTsase is 10U. /g;
  • the mass of the composite enzyme is 10% of the mass of the starch milk, and the enzymatic hydrolysis is carried out under the conditions of pH 4.3 and temperature of 55 ° C, and the enzymatic hydrolysis time is 48 h to obtain an enzymatic hydrolysate;
  • the high content trehalose product has a trehalose content of 100.56%, a yield of 99.8%, a granule degree of 30 mesh or less, 70% or more, a granule degree of 40 mesh or less, 60% or more, and 200 mesh or more, 90% or more. More than %; good water retention, used for baking, the bulkiness of the baked product is high. After 5 days at 4 °C, the hardness value is 357, which can prolong the storage time.
  • the moisturizing ability of cosmetics is not added with trehalose. 1.6 times or so; the incidence of baking Maillard reaction can be reduced by more than 50%, the color protection ability of fruits and vegetables is strong, and the shelf life of fruits and vegetables can be prolonged.
  • High-content trehalose preparation method which specifically comprises: (1) starch milk preparation, (2) liquefaction, (3) double enzymatic hydrolysis, (4) filtration to remove protein, (5) decolorization, (6) desalting, (7) Purification, (8) concentrated crystallization, (9) separation and drying;
  • Preparation of starch milk Take corn soaked into water, the ratio of corn to water is 5:2, the temperature of soaking water is 40 °C, soaked until the seed coat of corn can be peeled off, get soaked corn; filter water and soak corn The crushing is carried out to separate the seed coat to a whole grain amount of 8 grains/100 g to obtain crushed corn; the crushed corn is ground to remove the germ in the corn, and the amount of the corn germ in the slurry is 3/100 ml, and the slurry is obtained. The polishing liquid is disc separated, and the protein content in the polishing liquid is 10% to obtain starch milk;
  • Double enzymatic hydrolysis (2) After liquefaction is completed, complex enzyme is added to the liquefaction solution.
  • the complex enzyme includes MThase and MTsase.
  • the mass ratio of MThase to MTsase is 2:1, and the activity of MThase and MTsase is 1U. /g;
  • the mass of the composite enzyme is 5% of the mass of the starch milk, and the enzymatic hydrolysis is carried out at a pH of 4.0 and a temperature of 48 ° C, and the enzymatic hydrolysis time is 60 h to obtain an enzymatic hydrolyzate;
  • the high content trehalose product has a trehalose content of 100.1%, a yield of 99.7%, a granule degree of 30 mesh or less, 70% or more, a particle size of 40 mesh or less, 60% or more, and 200 mesh or more. More than %; good water retention, used for baking, the bulkiness of the baked product is high. After 5 days at 4 °C, the hardness value is 372, which can prolong the storage time. For cosmetics, the moisturizing ability of cosmetics is not added with trehalose. 1.5 times; the incidence of baking Maillard reaction can be reduced by more than 50%, the color protection ability of fruits and vegetables is strong, and the shelf life of fruits and vegetables can be prolonged.
  • High-content trehalose preparation method which specifically comprises: (1) starch milk preparation, (2) liquefaction, (3) double enzymatic hydrolysis, (4) filtration to remove protein, (5) decolorization, (6) desalting, (7) Purification, (8) concentrated crystallization, (9) separation and drying;
  • Double enzymatic hydrolysis (2) After liquefaction is completed, complex enzyme is added to the liquefaction solution.
  • the complex enzyme includes MThase and MTsase.
  • the mass ratio of MThase to MTsase is 2:1, and the activity of MThase and MTsase is 20U. /g;
  • the mass of the composite enzyme is 15% of the mass of the starch milk, and the enzymatic hydrolysis is carried out at a pH of 4.5 and a temperature of 62 ° C, and the enzymatic hydrolysis time is 36 h to obtain an enzymatic hydrolyzate;
  • the trehalose content in the high content trehalose product is 100.21%, the yield is 100.1%, the granulity is less than 30 mesh, accounting for more than 70%, the granulity is less than 40 mesh, accounting for more than 60%, and the above 200 mesh is 90%. More than %; good water retention, used for baking, the bulkiness of the baked product is high. After 5 days at 4 °C, the hardness value is 369, which can prolong the storage time.
  • the moisturizing ability of cosmetics is not added with trehalose. 1.4 times or so; the incidence of baking Maillard reaction can be reduced by more than 50%, the color protection ability of fruits and vegetables is strong, and the shelf life of fruits and vegetables can be prolonged.
  • the ordinary trehalose product and the present invention were respectively dissolved in the homogenized pure water and prepared into a sample having a concentration of 1%, which were respectively named as a control group and a test group, and the trehalose content was measured by a liquid chromatograph under the same conditions. Analysis, analysis results are shown in Table 1.
  • the trehalose content of the test group is higher than that of the control group, and the trehalose content of the test group is 101.2%, indicating that the trehalose content in the present invention is higher than that of the ordinary trehalose product, and the functionality of the present invention is superior to that of the ordinary trehalose product.
  • the same mask was prepared, and the common trehalose product (the trehalose content of 98%) and the present invention (the trehalose content of 99.7%) of the mass ratio of 3% were added under the same conditions and the same amount, and the ordinary trehalose product was used.
  • the mask was used as a control group, and the mask made by using the trehalose product of the present invention was used as a test group; the test group and the control group were placed at a temperature of 26 ° C and other environmental conditions were the same for 8 hours, and the moisture in the mask was detected by a rapid moisture meter.
  • Table 2 The results are shown in Table 2.
  • the ordinary trehalose product (havage content of 98%) and the present invention (trehalose content of 99.7%) are dissolved in the same solvent and prepared into a solution having a concentration of 20%, and the solution prepared from the ordinary trehalose product is a control group.
  • the solution prepared by the invention was a test group, and a mass ratio of 1% proline was added to the control group and the test group, and the solution was fully dissolved.
  • the control group and the test group were respectively placed in a water bath at 100 ° C, and the Maillard reaction was carried out after 30 minutes. The observation results are shown in Table 3.

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Abstract

L'invention concerne une méthode de préparation de tréhalose à teneur élevée. La méthode comprend séquentiellement les étapes suivantes : (1) préparation de lait d'amidon ; (2) liquéfaction ; (3) réalisation d'une double enzymolyse ; (4) filtration pour éliminer la protéine ; (5) décoloration ; (6) dessalement ; (7) réalisation d'une nanofiltration et d'une séparation chromatographique et d'une purification ; (8) réalisation d'une concentration et d'une cristallisation ; et (9) séparation et séchage pour obtenir un produit fini.
PCT/CN2018/097577 2018-01-26 2018-07-27 Méthode de préparation de tréhalose à teneur élevée WO2019144589A1 (fr)

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JP2020562807A JP7062090B2 (ja) 2018-01-26 2018-07-27 高含有量トレハロースの製造方法

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CN201810079531.2A CN108130350B (zh) 2018-01-26 2018-01-26 高含量海藻糖的制备方法

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CN113142279A (zh) * 2021-04-12 2021-07-23 宁波大学 一种适用于海鲜风味烘焙食品的蛋白液及其制备方法
CN117887784A (zh) * 2024-03-13 2024-04-16 山东天力药业有限公司 一种由淀粉制备海藻糖的方法

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CN112079885A (zh) * 2020-09-14 2020-12-15 江苏省奥谷生物科技有限公司 一种无水海藻糖的制备方法

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CN113142279A (zh) * 2021-04-12 2021-07-23 宁波大学 一种适用于海鲜风味烘焙食品的蛋白液及其制备方法
CN113142279B (zh) * 2021-04-12 2023-08-18 宁波大学 一种适用于海鲜风味烘焙食品的蛋白液及其制备方法
CN117887784A (zh) * 2024-03-13 2024-04-16 山东天力药业有限公司 一种由淀粉制备海藻糖的方法
CN117887784B (zh) * 2024-03-13 2024-06-04 山东天力药业有限公司 一种由淀粉制备海藻糖的方法

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TWI754125B (zh) 2022-02-01
CN108130350B (zh) 2021-08-24

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