CN111593046A - Immobilized magnetoenzyme preparation method of OPL grease - Google Patents

Immobilized magnetoenzyme preparation method of OPL grease Download PDF

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Publication number
CN111593046A
CN111593046A CN202010299599.9A CN202010299599A CN111593046A CN 111593046 A CN111593046 A CN 111593046A CN 202010299599 A CN202010299599 A CN 202010299599A CN 111593046 A CN111593046 A CN 111593046A
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immobilized
lipase
palmitic acid
opl
grease
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杨福明
于殿宇
陈奎任
陈妍
张欣
唐洪琳
郝凯越
刘天一
王立琦
江连洲
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Northeast Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
    • C12N11/14—Enzymes or microbial cells immobilised on or in an inorganic carrier
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
    • C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
    • C12N11/10—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a carbohydrate
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
    • C12N9/18—Carboxylic ester hydrolases (3.1.1)
    • C12N9/20—Triglyceride splitting, e.g. by means of lipase
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6454—Glycerides by esterification
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6436—Fatty acid esters
    • C12P7/6445—Glycerides
    • C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y301/00—Hydrolases acting on ester bonds (3.1)
    • C12Y301/01—Carboxylic ester hydrolases (3.1.1)
    • C12Y301/01003—Triacylglycerol lipase (3.1.1.3)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
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  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention relates to a preparation method of immobilized magnetoenzyme of OPL grease. The preparation method firstly uses nano-scale Fe3O4Preparing a novel magnetic carrier from the particles, and adhering the esterified synthetic enzyme and the position-specific lipase to the magnetic carrier to respectively obtain the immobilized esterified synthetic lipase and the immobilized position-specific lipase. Then, the OPL structure grease is prepared by adopting two-step immobilized magnetic enzyme catalysis. In the first step, palmitic acid and glycerol are used as raw materials, immobilized esterification synthesis lipase is used as a catalyst, and high-quality palmitic acid triglyceride is prepared. Secondly, the palmitic acid triglyceride, the oleic acid and the linoleic acid are used as raw materials, and the OPL grease is prepared by the catalytic reaction of the immobilized position specific lipaseAnd (3) obtaining a crude product. And finally, purifying the product by utilizing molecular distillation to obtain the OPL structure grease with higher content. The invention can further improve the preparation technology of the OPL grease, and the OPL structure grease can be industrially applied as soon as possible.

Description

Immobilized magnetoenzyme preparation method of OPL grease
Technical Field
The invention relates to a preparation method of immobilized magnetoenzyme of OPL grease.
Background
The breast milk contains various nutrient substances and is the best food source for the growth and development of the newborn. The breast milk contains 3% -5% of fat in various nutrient substances, and the fat provides unsaturated fatty acid required by infants and provides most energy for the growth and development of the infants. It was found that 98% of breast milk fat is triglycerides, about 1% is phospholipids, and 0.5% is cholesterol and cholesterol esters. The triglyceride structure in breast milk is highly specific, and 60% -70% of saturated fatty acids (palmitic acid) in the triglyceride are esterified at the Sn-2 position of the triglyceride and unsaturated fatty acids (oleic acid and linoleic acid) are at the Sn-1 and Sn-3 positions. Currently, there are two main classes of structural esters identified in breast milk: 1, 3-dioleoyl-2-palmitic acid triglyceride (OPO) and 1-oleic-2-palmitic-3-linoleic acid triglyceride (OPL), and the existence of the two structure-specific esters is beneficial to the high-efficiency absorption of breast milk fat by infants. The content of OPO and OPL in breast milk fat of people in different regions is different, and the content of OPL in breast milk in some regions is higher than that of OPO.
The infant formula milk powder is a milk substitute with similar nutritional composition and function to breast milk, and is prepared scientifically by adding or extracting certain components in the milk to ensure that the composition of the milk powder is close to the breast milk in quantity and biological function as much as possible. The positions of fatty acids on triglyceride can influence the digestion and absorption of the triglyceride, most of palmitic acid of cow milk and common vegetable oil is distributed on Sn-1,3 positions of the triglyceride, and the palmitic acid of Sn-1,3 positions can obtain free palmitic acid after being hydrolyzed by pancreatic lipase in vivo, so that the palmitic acid can easily form high-melting-point soap with calcium and magnesium ions in vivo and is discharged out of body, and constipation and mineral and energy loss of infants are caused. The OPO oil is gradually applied to infant formula milk powder in China from 2008, so that the constipation of infants and the loss of nutrient substances such as palmitic acid, calcium and the like are reduced. However, the development of another OPL structural grease is not enough at present, a real product is not formed, and a long way is left to the aim of applying the OPL structural grease to infant formula milk powder. The OPL oil is rich in linoleic acid, the linoleic acid is an essential fatty acid for human bodies, has the effects of reducing cholesterol and preventing atherosclerosis, and the linoleic acid is a nutrient substance for the development of the brain and optic nerves of infants and has important effects on improving the intelligence and enhancing the visual acuity of the infants. Infants lack linoleic acid, which causes skin disease, growth retardation, etc. Compared with OPO structure grease, the OPL grease not only can reduce constipation of infants and promote palmitic acid and mineral substance absorption, but also has the effect of improving intelligence and vision level of infants. Therefore, the development demand of the OPL structure grease product is urgent, and particularly, the efficient preparation method of the OPL grease is more important.
The enzyme is widely researched and applied in the field of biochemistry as a catalyst, and has the remarkable advantages of mild catalytic conditions, strong specificity, simple reaction equipment, low energy consumption, less environmental pollution and the like. At present, enzymes are widely applied in the fields of medicine, food production, chemical industry, agriculture and the like. The Sn-1, 3-specific lipase is a key biocatalyst in OPL synthesis, and after the Sn-1, 3-specific lipase is immobilized, the recycling frequency and specific activity of the lipase can be improved, the specificity of the lipase is ensured, and the production cost and market price of OPL structure grease are obviously reduced.
The enzyme is immobilized on a carrier, so that the enzyme has high stability and can be repeatedly used, and the application of the enzyme is greatly promoted due to the immobilized enzyme. Among a wide variety of immobilized enzyme carriers, a magnetic carrier becomes an important immobilized carrier due to its unique magnetic characteristics. The magnetic composite microsphere is a novel functional material formed by connecting and combining magnetic nanoparticles and organic high molecules by a certain method. The magnetic composite microsphere is a composite material which is newly researched and has not only the magnetic responsiveness of a magnetic material but also a plurality of characteristics of a high polymer material. Meanwhile, various functional groups with reactivity can be introduced on the surface of the composite microsphere by methods of chemical modification, copolymerization and the like, so that the dispersibility and biocompatibility of the composite microsphere are effectively improved, and more importantly, active groups on the surface of the composite microsphere can be combined with biological macromolecules such as enzyme, antibody, protein, nucleic acid and the like in modes of intermolecular force or covalent bond and the like. In addition, due to the higher magnetic effect, the composite microspheres can be quickly separated and positioned under the action of a magnetic field. Therefore, magnetic immobilized carriers are widely applied to various fields such as biomedical sensors, wastewater treatment, electrochemistry, biomedicine, catalytic synthesis, immobilized enzymes, targeted drugs and the like, and are hot spots for lipase carrier research in recent years.
Research on the directional enzymatic synthesis of OPL grease by using immobilized magnetic biological enzyme is not reported, and the glycerol skeleton of the OPL grease molecule is respectively connected with three different fatty acids, namely oleic acid, palmitic acid and linoleic acid, so that the synthesis of OPL is more difficult than that of OPO. The invention aims to provide a preparation method of OPL structure grease, which has mild reaction conditions, strong specificity, high product content and recyclable enzyme, by adopting immobilized magnetoenzyme as a catalyst.
Disclosure of Invention
The technical scheme adopted by the invention is summarized as follows:
(1) with nanoscale Fe3O4The particles are magnetic matrixes, edible polysaccharide is used as a carrier, and the magnetic nanoparticles are wrapped by the adhesion of a cross-linking agent to prepare the novel magnetic carrier. Then, the esterification synthetase and the position specific lipase are adhered to a magnetic carrier under the action of a cross-linking agent to respectively obtain the immobilized esterification synthetic lipase and the immobilized position specific lipase.
Wherein the edible polysaccharide is sodium alginate, dialdehyde starch, carboxymethyl chitosan or a compound mixture thereof; the cross-linking agent is glutaraldehyde, polydopamine, 3, 4-dihydroxybenzaldehyde or a compound mixture thereof; the position specific lipase is a compound mixture of Sn-1,3 lipase, Sn-1 lipase and Sn-3 lipase.
(2) Weighing 1 mol of palmitic acid in a beaker, adding glycerol with a mol ratio (1.1-2.0):1 to the palmitic acid, adding immobilized esterification synthetic lipase with a mol number of 3-8% of the palmitic acid, and reacting for 8-12 hours in a water bath at a constant temperature of 30-50 ℃ and a rotation speed of 50-120 rpm of a non-metal stirrer. And after the reaction is finished, adding 2-4 times of water with the volume of 20-25 ℃ into the beaker, fully stirring and uniformly mixing, removing the immobilized esterification synthetic lipase by magnetic attraction, standing at room temperature, and separating an upper layer substance after layering to obtain the high-quality palmitic acid triglyceride.
(3) Weighing 1 mol of palmitic acid triglyceride in a beaker, respectively adding oleic acid and linoleic acid with a mol ratio (0.8-1.2) to the palmitic acid triglyceride of 1, and adding immobilized position specific lipase with a mol number of the palmitic acid triglyceride of 2.5-6.5%, keeping a constant temperature of 35-50 ℃ in a water bath, and reacting for 8-12 hours at a rotation speed of 50-120 rpm of a non-metal stirrer. After the reaction, the immobilized site-specific lipase was removed by magnetic attraction. And controlling the temperature of the reaction product at 115-135 ℃ under the vacuum condition, and removing free oleic acid, linoleic acid and palmitic acid in the reaction system by molecular distillation to finally obtain the OPL grease with the content of 35-50%.
The specific implementation mode is as follows:
the first embodiment is as follows:
(1) with nanoscale Fe3O4The particles are magnetic matrixes, dialdehyde starch is adopted as a carrier, and the magnetic nanoparticles are wrapped by the adhesion effect of glutaraldehyde to prepare the novel magnetic carrier. Then, the esterification synthetase and the Sn-1,3 lipase are adhered to a magnetic carrier under the action of glutaraldehyde to respectively obtain immobilized esterification synthetic lipase and immobilized position specific lipase.
(2) Weighing 1 mol of palmitic acid in a beaker, adding glycerol with the mol ratio of 1.2:1 to the palmitic acid, adding immobilized esterification synthetic lipase with the mol ratio of 6% of the palmitic acid, and reacting for 10 hours in a water bath at a constant temperature of 45 ℃ under the rotation speed of 80 rpm of a nonmetal stirrer. And after the reaction is finished, adding 3 times of water with the volume of 25 ℃ into the beaker, fully stirring and uniformly mixing, removing the immobilized esterification synthetic lipase by magnetic attraction, standing at room temperature, and separating an upper layer substance after layering to obtain the high-quality palmitic acid triglyceride.
(3) Weighing 1 mol of palmitic acid triglyceride in a beaker, respectively adding oleic acid and linoleic acid with the mol ratio of 1.0:1 to the palmitic acid triglyceride, and adding immobilized Sn-1,3 lipase with the mol ratio of 4.5% of the palmitic acid triglyceride, and reacting for 10 hours in a water bath at a constant temperature of 45 ℃ and a rotation speed of 80 rpm of a non-metal stirrer. After the reaction, the immobilized Sn-1,3 lipase was removed by magnetic attraction. And (3) controlling the temperature of the reaction product to 120 ℃ under the vacuum-pumping condition, and removing free oleic acid, linoleic acid and palmitic acid in the reaction system by molecular distillation to finally obtain the OPL grease with the content of 40%.
The second embodiment is as follows:
(1) with nanoscale Fe3O4The particles are magnetic matrixes, a dialdehyde starch and carboxymethyl chitosan compound is used as a carrier, and the magnetic nanoparticles are wrapped by the adhesion effect of glutaraldehyde to prepare the novel magnetic carrier. Then, the esterification synthetase and the Sn-1,3 lipase are adhered to a magnetic carrier under the action of glutaraldehyde to respectively obtain immobilized esterification synthetic lipase and immobilized position specific lipase.
(2) Weighing 1 mol of palmitic acid in a beaker, adding glycerol with the mol ratio of 1.4:1 to the palmitic acid, adding immobilized esterification synthetic lipase with the mol ratio of 8% of the palmitic acid, and reacting for 12 hours in a water bath at a constant temperature of 50 ℃ under the rotating speed of 60 revolutions per minute of a nonmetal stirrer. And after the reaction is finished, adding 4 times of volume of 25 ℃ water into the beaker, fully stirring and uniformly mixing, removing the immobilized esterified synthetic lipase by magnetic attraction, standing at room temperature, and separating an upper layer substance after layering to obtain the high-quality palmitic acid triglyceride.
(3) Weighing 1 mol of palmitic acid triglyceride in a beaker, respectively adding oleic acid and linoleic acid with the mol ratio of 1.2:1 to the palmitic acid triglyceride, and adding immobilized Sn-1,3 lipase with the mol number of the palmitic acid triglyceride of 6.0%, and reacting for 12 hours in a water bath at a constant temperature of 50 ℃ and a rotation speed of 60 revolutions per minute of a non-metal stirrer. After the reaction, the immobilized Sn-1,3 lipase was removed by magnetic attraction. And (3) controlling the temperature of the reaction product to 130 ℃ under the vacuum-pumping condition, and removing free oleic acid, linoleic acid and palmitic acid in the reaction system by molecular distillation to finally obtain the OPL grease with the content of 45%.

Claims (2)

1. A preparation method of immobilized magnetoenzyme of OPL grease comprises the following steps:
(1) with nanoscale Fe3O4The particles are magnetic matrixes, edible polysaccharide is used as a carrier, and the magnetic nanoparticles are wrapped by the adhesion of a cross-linking agent to prepare a novel magnetic carrier; then, the esterification synthetase and the position specific lipase are adhered to a magnetic carrier under the action of a cross-linking agent to respectively obtain immobilized esterification synthetic lipase and immobilized position specific lipase;
(2) weighing 1 mol of palmitic acid in a beaker, adding glycerol with a mol ratio (1.1-2.0):1 to the palmitic acid, adding immobilized esterification synthetic lipase with a mol number of 3-8% of the palmitic acid, and reacting for 8-12 hours in a water bath at a constant temperature of 30-50 ℃ under a rotation speed of 50-120 rpm of a non-metal stirrer; after the reaction is finished, adding 2-4 times of water with the volume of 20-25 ℃ into a beaker, fully stirring and uniformly mixing, removing the immobilized esterification synthetic lipase by magnetic attraction, standing at room temperature, and separating an upper layer substance after layering to obtain high-quality palmitic acid triglyceride;
(3) weighing 1 mol of palmitic acid triglyceride in a beaker, respectively adding oleic acid and linoleic acid with a mol ratio (0.8-1.2) to the palmitic acid triglyceride of 1, and adding immobilized position specific lipase with a mol number of the palmitic acid triglyceride of 2.5-6.5%, keeping a constant temperature of 35-50 ℃ in a water bath, and reacting for 8-12 hours at a rotation speed of 50-120 rpm of a non-metal stirrer; after the reaction is finished, removing the specific lipase at the immobilized position by magnetic attraction, controlling the temperature of the reaction product to be 115-135 ℃ under the vacuum condition, and removing free oleic acid, linoleic acid and palmitic acid in the reaction system by molecular distillation to finally obtain the OPL grease with the content of 35-50%.
2. The edible polysaccharide of claim 1, which is sodium alginate, dialdehyde starch, carboxymethyl chitosan or a compound mixture thereof; the cross-linking agent is glutaraldehyde, polydopamine, 3, 4-dihydroxybenzaldehyde or a compound mixture thereof; the position specific lipase is a compound mixture of Sn-1,3 lipase, Sn-1 lipase and Sn-3 lipase.
CN202010299599.9A 2020-04-16 2020-04-16 Immobilized magnetoenzyme preparation method of OPL grease Pending CN111593046A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113881661A (en) * 2021-09-29 2022-01-04 淮阴工学院 Method for immobilizing enzyme by magnetic nanoparticles based on carboxymethyl starch modification
CN117625586A (en) * 2023-11-23 2024-03-01 广东惠尔泰生物科技有限公司 Sn-1,3 specific immobilized lipase, and preparation method and application thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102757988A (en) * 2012-07-25 2012-10-31 浙江大学 Preparation method of 1,3-dioleoyl-2-palmitoyl triglyceride
CN104313010A (en) * 2014-11-05 2015-01-28 太原理工大学 Preparation method of magnetic response composite lipase and application in biodiesel synthesis
CN104357499A (en) * 2014-10-09 2015-02-18 杭州恒诺科技有限公司 Preparation method for grease with structure close to human milk fat structure
CN109468349A (en) * 2018-11-15 2019-03-15 江南大学 A kind of method that enzyme process prepares 1- oleic acid -2- palmitinic acid -3- linoleic acid triglyceride

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102757988A (en) * 2012-07-25 2012-10-31 浙江大学 Preparation method of 1,3-dioleoyl-2-palmitoyl triglyceride
CN104357499A (en) * 2014-10-09 2015-02-18 杭州恒诺科技有限公司 Preparation method for grease with structure close to human milk fat structure
CN104313010A (en) * 2014-11-05 2015-01-28 太原理工大学 Preparation method of magnetic response composite lipase and application in biodiesel synthesis
CN109468349A (en) * 2018-11-15 2019-03-15 江南大学 A kind of method that enzyme process prepares 1- oleic acid -2- palmitinic acid -3- linoleic acid triglyceride

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113881661A (en) * 2021-09-29 2022-01-04 淮阴工学院 Method for immobilizing enzyme by magnetic nanoparticles based on carboxymethyl starch modification
CN117625586A (en) * 2023-11-23 2024-03-01 广东惠尔泰生物科技有限公司 Sn-1,3 specific immobilized lipase, and preparation method and application thereof

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