CN103667397A - Method for synthesizing 3-O-beta-D-galactosyl glyceride through enzyme catalysis method - Google Patents
Method for synthesizing 3-O-beta-D-galactosyl glyceride through enzyme catalysis method Download PDFInfo
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Abstract
The invention discloses a method for preparing 3-O-beta-D-galactosyl glycerin fatty acid ester through an enzyme method, which comprises the following steps: by taking lipase as a catalyst, performing esterification reaction on 3-O-beta-D-galactosyl glycerol and fatty acid in an organic solvent system; and separating, and refining to obtain 3-O-beta-D-galactosyl monoglyceride and diglyceride. The method disclosed by the invention has the advantages of mild reaction conditions, high reaction selectivity, safe reaction medium, simple process, low cost and the like.
Description
Technical field
The invention belongs to biocatalysis technology field, be specifically related to the method that enzyme process is prepared 3-O-β-D galactosyl glyceryl ester (monoesters and diester).
Background technology
Galactosyl glyceroglycolipid is semi-lactosi by its reduction end with α-or compounds of being connected together of β-glycosidic link and lipophilic long-chain monoester acyl group or two fatty acyl group glycerine.Galactosyl glyceroglycolipid has surfactivity, antiviral, antitumor, antibacterial, anti-inflammatory, effect, the especially anti-tumor activity such as anti-oxidant have caused showing great attention to of people.In addition galactosyl glyceroglycolipid aspect the thermotolerance of bacterium and the plant activity that realizes photosynthesis aspect also have relevant research report.These researchs have affirmed that the potential edible medicinal of galactosyl glycerine sugar ester is worth and biological study meaning.
According to preparation method's difference, glyceroglycolipid can be divided into natural glycerin glycolipid and synthetic glycerine glycolipid.Natural glycerin glycolipid obtains through separation and Extraction from plant or algae.Because the content of glyceroglycolipid in natural phant or algae is very low, and exist mainly with the form of mixture, separation and purification difficulty, so natural glycerin glycolipid production cost is high, can not meet the need of market.In Sigma goods catalogue, show purity 95% monogalactosyl diglyceride (extracting from flour), the price of 1mg is 3580.2 yuan.Therefore, synthetic glyceroglycolipid is the most effective terms of settlement.According to bibliographical information, the preparation method of galactosyl glyceryl ester has a lot, as:
Morinoto?et?al.,Tetrahedron?1995,51(23):6443-6450
Precursor glycosyl glycerine is synthetic by complicated chemical process, and acry radical donor is vinyl acetate, and expensive, reaction is carried out in pyridine, and environment is had to pollution.
Cateni?et?al.,Bioorganic?&?Medicinal?Chemistry?Letters,2007,17:1971-1978
Precursor glycosyl glycerine is that chemical method is synthetic, complex process, and acry radical donor is vinyl acetate, expensive, and reaction is carried out in pyridine, and final product also needs to operate by complicated deprotection.Complex process, cost is high, and environment is had to pollution.
Marjolein?Woudenberg-Van?Oosterom.Doctoral?dissertation.Technische?Universiteit
Delft.1996
Also there is the deficiency that production cost is high in the method.
The synthetic cost of above-mentioned several method is high, and complex process is large or cannot effectively realize galactosyl glycerine and be connected with the direct acylations of free fatty acids to environmental hazard.
Summary of the invention
For the amount existing in prior art glyceroglycolipid preparation process less rare, selectivity is not high, complex process, cost is high, easily to shortcomings such as environments, the invention provides a kind of method of simple to operate, the reaction times is shorter, environmental pollution is less, selectivity is high, reaction conditions the is gentle synthetic 3-O-β-D galactosyl glyceryl ester of enzyme catalysis method.
The present invention is achieved in that
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of a kind of enzyme catalysis method of the present invention, comprises the following steps:
Enzymatic esterification: lipase joins in the organic solvent that contains 3-O-β-D galactosyl glycerine and lipid acid, carries out enzymically hydrolyse reaction, then adds molecular sieve to continue reaction;
Filter and remove lipase;
3-O-β-D galactosyl glyceryl ester is carried out to separation and purification, obtain.
The reaction formula of enzymatic esterification of the present invention is as follows:
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of above-described a kind of enzyme catalysis method, the lipid acid in its enzymatic esterification is a kind of in caproic acid, capric acid, lauric acid, palmitinic acid, stearic acid, oleic acid, linolic acid or linolenic acid.
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of above-described a kind of enzyme catalysis method, the organic solvent in its enzymatic esterification is a kind of in acetone, the trimethyl carbinol, acetonitrile, tertiary amyl alcohol or methylene dichloride.
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of above-described a kind of enzyme catalysis method, the catalyzer lipase in its enzymatic esterification is a kind of in Novozyme435 lipase, pseudomonas cepacia lipase or LipozymeRMIM lipase.
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of above-described a kind of enzyme catalysis method, in its enzymatic esterification, the molar concentration rate of 3-O-β-D galactosyl glycerine and lipid acid is 1:8～1:20, the add-on of lipase is 10～30mg/ml, and the add-on of molecular sieve is 70～80mg/ml.
The add-on of described lipase is that the ml in 10～30mg/ml is the volume with respect to 3-O-β-D galactosyl glycerine and lipid acid, and the add-on of molecular sieve is that the ml in 70～80mg/ml is the volume with respect to 3-O-β-D galactosyl glycerine, lipid acid and molecular sieve.
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of above-described a kind of enzyme catalysis method, the described molecular sieve of step (1) is 4A molecular sieve, at enzymically hydrolyse, within reacted the 3rd hour, adds.
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of above-described a kind of enzyme catalysis method, the enzymatic esterification of step (1) carries out in shaking bath, and shaking speed is 150～170rpm, and the reaction times is 5～15h, and temperature of reaction is 40～55 ℃.
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of above-described a kind of enzyme catalysis method, in step (2), separating out fat enzyme adopts the mode of filtering.
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of above-described a kind of enzyme catalysis method, the separation and purification of step (3) is followed successively by vacuum rotating and silica gel column chromatography.
The method of the synthetic 3-O-β-D galactosyl glyceryl ester of above-described a kind of enzyme catalysis method, after vacuum rotating, before silica gel column chromatography with the extraction of chloroform-water.
The separation purification method of step (3) is with the extraction of chloroform-water, more respectively chloroform phase and water is carried out to column chromatography, obtains respectively the elutriant that contains 3-O-β-D galactosyl glycerine dibasic acid esters and 3-O-β-D galactosyl monoglyceride.This step can by 3-O-β-D galactosyl glyceryl ester from reaction night with the separation of by-products of unreacted 3-O-β-D galactosyl glycerine, lipid acid and generation.
Reaction equation of the present invention is as follows:
In formula, work as R
1=H, R
2=caproic acid, capric acid, lauric acid, palmitinic acid, stearic acid, oleic acid, linolic acid, linolenic acid a kind of or R wherein
1=caproic acid, capric acid, lauric acid, palmitinic acid, stearic acid, oleic acid, linolic acid, linolenic acid a kind of, R wherein
2during=H, represent galactosyl monoglyceride (MGMGs); R
1=R
2during wherein a kind of of=caproic acid, capric acid, lauric acid, palmitinic acid, stearic acid, oleic acid, linolic acid, linolenic acid, represent galactosyl triglyceride (MGDGs).
It is raw material that D-semi-lactosi and glycerine are take in the preparation of 3-O-β-D galactosyl glycerine, and preparation method is as follows:
By D-semi-lactosi and glycerine mol ratio, be that to add pH be in 6.5 phosphoric acid buffer to 1:10, wherein damping fluid content is 60% of substrate volume, the beta-galactosidase enzymes (deriving from Kluyveromyces lactis) that adds 350U/ml in 40 ℃ of water-baths after preheating 30min, reaction 48h.After reaction finishes, at 100 ℃ of boiling water baths, boil the 3min enzyme that goes out and live.The rear gac column separating purification of crossing, gac is after the immersion of spending the night is degassed, dress post 26 * 600mm, reaction solution loading 20ml, use respectively deionized water, 3%, 9%, 20% aqueous ethanolic solution wash-out, each gradient elution 400ml, the elutriant that 9% gradient is obtained obtains 3-O-β-D galactosyl glycerine sterling through rotary evaporation, lyophilize.
Advantage of the present invention:
The present invention compared with prior art, product 3-O-β-D galactosyl glycerine and free fatty acids that the simple enzyme catalysis method of take obtains are substrate, with the Biocatalysis method selectivity of environmental protection, prepare serial 3-O-β-D galactosyl monoglyceride and diester, production cost is low, reaction conditions is gentle, easy and simple to handle, later separation purification process is easy, product purity is high.
Accompanying drawing explanation
Fig. 1 is the liquid phase figure of 3-O-β-D galactosyl glycerine caproic acid monoesters (A).
Fig. 2 is the liquid phase figure of 3-O-β-D galactosyl glycerine caproic acid diester (B).
Embodiment
Below in conjunction with embodiment, the specific embodiment of the present invention is elaborated.
Embodiment 1
Take 3-O-β-D galactosyl glycerine 0.1mmol, n-caproic acid 1.6mmol, lipase Novozym43525mg and acetone 1ml and be placed in 10ml tool plug test tube, be placed in 40 ℃, in 150r/min shaking bath, oscillatory reaction is 3 hours, adds 80mg/ml4A molecular sieve to dewater, and continues to react to 8h.After reaction finishes, first logical filtration method is removed lipase, again filtrate vacuum-evaporation is removed to organic solvent, then by chloroform/water, extract, after chloroform phase and water are concentrated, carry out silica gel column chromatography, obtain respectively the elutriant containing 3-O-β-D galactosyl glycerine caproic acid diester and 3-O-β-D galactosyl glycerine caproic acid monoesters, HPLC-ELSD detects.Testing conditions is: chromatographic column is ZORBASBC18 chromatographic column (5 μ m, 4.6mm * 250mm, Agilent, U.S.A.), and moving phase is 80% methyl alcohol: 20% water (V/V), flow rate of mobile phase remains on 0.5ml/min.ELSD detector parameters: 55 ℃ of drift tube temperatures, ELSD yield value is 1, carrier gas is nitrogen, pressure 0.5MPa, wash-out 12min.The liquid chromatogram of 3-O-β-D galactosyl glycerine caproic acid monoesters and diester is shown in Fig. 1 and Fig. 2.It is that the purity of 74.17%, 3-O-β-D galactosyl glycerine caproic acid diester and 3-O-β-D galactosyl glycerine caproic acid monoesters is respectively 100% and 85% that mensuration obtains transformation efficiency.
Take 3-O-β-D galactosyl glycerine 0.1mmol, lauric acid 1.8mmol, lipase Novozyme43520mg and acetone 1ml and be placed in 10ml tool plug test tube, be placed in 50 ℃, in 150r/min shaking bath, oscillatory reaction is 3 hours, add 80mg4A molecular sieve (in order to dewater), continue to react to 10.5h.After reaction finishes, first logical filtration method is removed lipase, again filtrate vacuum-evaporation is removed to organic solvent, then carry out silica gel column chromatography, obtain respectively the elutriant containing 3-O-β-D galactosyl glycerine lauric acid diester and 3-O-β-D galactosyl glycerine lauric acid monoester, HPLC-ELSD detects, and the purity of 3-O-β-D galactosyl glycerine lauric acid diester and 3-O-β-D galactosyl glycerine lauric acid monoester is respectively 100% and 81%.
Embodiment 3
Take 3-O-β-D galactosyl glycerine 0.1mmol, palmitinic acid 1.0mmol, lipase Novozyme43520mg/ml and 1ml methylene dichloride are placed in 10ml tool plug test tube, be placed in 50 ℃, in 150r/min shaking bath, oscillatory reaction is 3 hours, add 70mg4A molecular sieve (in order to dewater), continue to react to 10.5h.After reaction finishes, first logical filtration method is removed lipase, again filtrate vacuum-evaporation is removed to organic solvent, then carry out silica gel column chromatography, obtain respectively the elutriant containing 3-O-β-D galactosyl glycerine palmitinic acid monoesters and 3-O-β-D galactosyl glycerine palmitinic acid diester, HPLC-ELSD detects, and the purity of 3-O-β-D galactosyl glycerine palmitinic acid monoesters and 3-O-β-D galactosyl glycerine palmitinic acid diester is respectively 72% and 98%.
Take 3-O-β-D galactosyl glycerine 0.1mmol, linolic acid 1.0mmol, lipase Novozyme43520mg and 1ml methylene dichloride and be placed in 10ml tool plug test tube, in reaction tube, after inflated with nitrogen, seal and be placed in 50 ℃, in 160r/min shaking bath, oscillatory reaction is 3 hours, add 70mg4A molecular sieve (in order to dewater), continue to react to 10.5h.After reaction finishes, first logical filtration method is removed lipase, again filtrate vacuum-evaporation is removed to organic solvent, then carry out silica gel column chromatography, obtain respectively the elutriant containing 3-O-β-D galactosyl glycerine linolic acid monoesters and 3-O-β-D galactosyl glycerine linolic acid diester, HPLC-ELSD detects, and the purity of 3-O-β-D galactosyl glycerine linolic acid monoesters and 3-O-β-D galactosyl glycerine linolic acid diester is respectively 75% and 87%.
Take 3-O-β-D galactosyl glycerine 0.1mmol, n-caproic acid 2.0mmol, lipase Novozyme43518mg and 1ml acetone and be placed in 10ml tool plug test tube, be placed in 50 ℃, in 150r/min shaking bath, oscillatory reaction is 3 hours, add 80mg4A molecular sieve (in order to dewater), continue to react to 10h.After reaction finishes, first logical filtration method is removed lipase, again filtrate vacuum-evaporation is removed to organic solvent, then by chloroform/water, extract, after chloroform phase and water are concentrated, carry out respectively silica gel column chromatography, obtain respectively the elutriant containing 3-O-β-D galactosyl glycerine caproic acid diester and 3-O-β-D galactosyl glycerine caproic acid monoesters, HPLC-ELSD detects, recording transformation efficiency is 88%, and the purity of gained 3-O-β-D galactosyl glycerine caproic acid diester and 3-O-β-D galactosyl glycerine caproic acid monoesters is respectively 100% and 85%.
Take 3-O-β-D galactosyl glycerine 0.1mmol, n-caproic acid 1.8mmol, Lipozyme RMIM30mg and 1ml acetone and be placed in 10ml tool plug test tube, be placed in 50 ℃, in 170r/min shaking bath, oscillatory reaction is 3 hours, add 80mg4A molecular sieve (in order to dewater), continue to react to 9h.After reaction finishes, first logical filtration method is removed lipase, again filtrate vacuum-evaporation is removed to organic solvent, then by chloroform/water, extract, after chloroform phase and water are concentrated, carry out respectively silica gel column chromatography, obtain respectively the elutriant containing 3-O-β-D galactosyl glycerine caproic acid diester and 3-O-β-D galactosyl glycerine caproic acid monoesters, HPLC-ELSD detects, obtain 3-O-β-D galactosyl glycerine caproic acid diester 2mg, 3-O-β-D galactosyl glycerine caproic acid monoesters 9mg.
Embodiment 7
Take 3-O-β-D galactosyl glycerine 0.1mmol, n-caproic acid 1.8mmol, lipase Novozym43520mg and 1ml acetone and be placed in 10ml tool plug test tube, be placed in 50 ℃, in 150r/min shaking bath, oscillatory reaction is 3 hours, add 80mg4A molecular sieve (in order to dewater), continue to react to 15h.After reaction finishes, first logical filtration method is removed lipase, again filtrate vacuum-evaporation is removed to organic solvent, then by chloroform/water, extract, after chloroform phase and water are concentrated, carry out respectively silica gel column chromatography, obtain respectively the elutriant containing 3-O-β-D galactosyl glycerine caproic acid diester and 3-O-β-D galactosyl glycerine caproic acid monoesters, HPLC-ELSD detects, and recording transformation efficiency is 83%.
Take 3-O-β-D galactosyl glycerine 0.1mmol, n-caproic acid 1.8mmol, lipase Novozym43520mg and the 1ml trimethyl carbinol and be placed in 10ml tool plug test tube, be placed in 50 ℃, in 150r/min shaking bath, oscillatory reaction is 3 hours, add 80mg4A molecular sieve (in order to dewater), continue to react to 9h.After reaction finishes, first logical filtration method is removed lipase, again filtrate vacuum-evaporation is removed to organic solvent, then by chloroform/water, extract, after chloroform phase and water are concentrated, carry out respectively silica gel column chromatography, obtain respectively the elutriant containing 3-O-β-D galactosyl glycerine caproic acid diester and 3-O-β-D galactosyl glycerine caproic acid monoesters, HPLC-ELSD detects, and recording transformation efficiency is 63%.
Embodiment 9
The product that separation and purification obtains, carries out ESI-MS evaluation to it.Mass Spectrometric Identification result is as follows, and 3-O-β-D galactosyl glycerine caproic acid monoesters and diester molecular weight thereof are: m/z:352,450; 3-O-β-D galactosyl glycerine capric acid monoesters and diester molecular weight are: m/z:408,562; 3-O-β-D galactosyl glycerine lauric acid monoester and diester molecular weight are: m/z:436,618; 3-O-β-D galactosyl glycerine palmitinic acid monoesters and diester molecular weight are: m/z:492,730; 3-O-β-D galactosyl glycerine stearate monoesters and diester molecular weight are: m/z:520,786; 3-O-β-D galactosyl glycerine oleic acid monoester and diester molecular weight are: m/z:518,782; 3-O-β-D galactosyl glycerine linolic acid monoesters and diester molecular weight are: m/z:516,778; 3-O-β-D galactosyl glycerine linolenic acid monoesters and diester molecular weight are: m/z:514,774.Illustrate that products therefrom is a series of 3-O-β-D galactosyl glyceryl ester.
3-O-β-D galactosyl glycerine caproic acid monoesters and diester thereof are identified through NMR.Nuclear magnetic resonance result is as follows: 3-O-β-D galactosyl glycerine caproic acid monoesters exists two kinds of isomerss, and caproic acid chain is connected to 1 hydroxyl of glycerine, its
13cNMR data are: δ
c: 173.107(C=O); Galactose residue: 104.034(l-C), 70.763(2-C), 73.388(3-C), 67.597(4-C), 72.283(5-C), 60.548(6-C); Glycerol residue: 63.587(sn-l-C), 65.401(sn-2-C), 68.250(sn-3-C).
Caproic acid is connected to galactosyl C6 ' position, its
13cNMR data are: δ
c: 173.107(C=O); Galactose residue: 104.034(l-C), 70.763(2-C), 73.388(3-C), 67.597(4-C), 71.973(5-C), 62.96(6-C); Glycerol residue: 64.064(sn-l-C), 65.558(sn-2-C), 68.250(sn-3-C).
The structure of galactosyl glycerine caproic acid diester is the galactose residue C6 ' position that caproic acid chain is combined in galactosyl glycerine simultaneously, and the C1 position of glycerine (1-O-hexanoyl-3-O-(6 '-O-hexanoyl-β-D-galactopyranosyl)-sn-glycerol).Its
13cNMR data are: δ
c: 172.914(C=O); 172.914(C=O); Galactose residue: 103.976(l-C), 70.504(2-C), 73.36(3-C), 67.598(4-C), 72.372(5-C); Glycerol residue: 63.608(sn-l-C), 65.271(sn-2-C), 68.55(sn-3-C).
Adopt cell in vitro culture method (MTT detection method) to know, the present invention also has good antitumous effect for cancer cells such as human gastric cancer cells BGC-823, human liver cancer cell HepG2, human breast cancer cell MCF-7.
Claims (10)
1. a method for the synthetic 3-O-β-D galactosyl glyceryl ester of enzyme catalysis method, is characterized in that, comprises the following steps:
Enzymatic esterification: lipase joins in the organic solvent that contains 3-O-β-D galactosyl glycerine and lipid acid, carries out enzymically hydrolyse reaction, then adds molecular sieve to continue reaction;
Filter and remove lipase;
3-O-β-D galactosyl glyceryl ester is carried out to separation and purification, obtain.
2. the method for the synthetic 3-O-β-D galactosyl glyceryl ester of enzyme catalysis method according to claim 1, is characterized in that: described lipid acid is a kind of in caproic acid, capric acid, lauric acid, palmitinic acid, stearic acid, oleic acid, linolic acid or linolenic acid.
3. the method for the synthetic 3-O-β-D galactosyl glyceryl ester of enzyme catalysis method according to claim 1, is characterized in that: described organic solvent is a kind of in acetone, the trimethyl carbinol, acetonitrile, tertiary amyl alcohol or methylene dichloride.
4. the method for the synthetic 3-O-β-D galactosyl glyceryl ester of enzyme catalysis method according to claim 1, is characterized in that: described lipase is a kind of in Novozyme 435 lipase, pseudomonas cepacia lipase or Lipozyme RMIM lipase.
5. enzyme catalysis method according to claim 1 synthesizes the method for 3-O-β-D galactosyl glyceryl ester, it is characterized in that: the molar concentration rate of 3-O-β-D galactosyl glycerine and lipid acid is 1:8～1:20, the add-on of lipase is 10 ~ 30mg/ml, and the add-on of molecular sieve is 70 ~ 80mg/ml.
6. the method for the synthetic 3-O-β-D galactosyl glyceryl ester of enzyme catalysis method according to claim 1, is characterized in that: the described molecular sieve of step (1) is 4A molecular sieve, at enzymically hydrolyse, within reacted the 3rd hour, adds.
7. enzyme catalysis method according to claim 1 synthesizes the method for 3-O-β-D galactosyl glyceryl ester, it is characterized in that: the enzymatic esterification of step (1) carries out in shaking bath, shaking speed is 150 ~ 170rpm, and the reaction times is 5 ~ 15h, and temperature of reaction is 40 ~ 55 ℃.
8. the method for the synthetic 3-O-β-D galactosyl glyceryl ester of enzyme catalysis method according to claim 1, is characterized in that: in step (2), separating out fat enzyme adopts the mode of filtering.
9. the method for the synthetic 3-O-β-D galactosyl glyceryl ester of enzyme catalysis method according to claim 1, is characterized in that: the separation and purification of step (3) is followed successively by vacuum rotating and silica gel column chromatography.
10. the method for the synthetic 3-O-β-D galactosyl glyceryl ester of enzyme catalysis method according to claim 9, is characterized in that: step (3) after vacuum rotating, before silica gel column chromatography with the extraction of chloroform-water.
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| CN104498543A (en) * | 2015-01-22 | 2015-04-08 | 中国石油大学(华东) | Method for synthesizing acetoin fatty acid ester in catalyzed mode through lipase |
| CN113317316A (en) * | 2020-02-29 | 2021-08-31 | 浙江工业大学 | Application of validamycin A ester in preparation of sclerotinia sclerotiorum inhibitor |
| CN113317317A (en) * | 2020-02-29 | 2021-08-31 | 浙江工业大学 | Application of validamycin A ester in preparation of aphid insecticide |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104498543A (en) * | 2015-01-22 | 2015-04-08 | 中国石油大学(华东) | Method for synthesizing acetoin fatty acid ester in catalyzed mode through lipase |
| CN104498543B (en) * | 2015-01-22 | 2017-10-31 | 中国石油大学(华东) | A kind of method of lipase-catalyzed synthesis 3-hydroxy-2-butanone fatty acid ester |
| CN113317316A (en) * | 2020-02-29 | 2021-08-31 | 浙江工业大学 | Application of validamycin A ester in preparation of sclerotinia sclerotiorum inhibitor |
| CN113317317A (en) * | 2020-02-29 | 2021-08-31 | 浙江工业大学 | Application of validamycin A ester in preparation of aphid insecticide |
| CN113317317B (en) * | 2020-02-29 | 2022-06-21 | 浙江工业大学 | Application of validamycin A ester in preparation of aphid insecticide |
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