CN104031957A - Method for synthesizing sucrose-6-ester under catalytic action of lipase promoted by constant magnetic field - Google Patents
Method for synthesizing sucrose-6-ester under catalytic action of lipase promoted by constant magnetic field Download PDFInfo
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- CN104031957A CN104031957A CN201410257672.0A CN201410257672A CN104031957A CN 104031957 A CN104031957 A CN 104031957A CN 201410257672 A CN201410257672 A CN 201410257672A CN 104031957 A CN104031957 A CN 104031957A
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Abstract
The invention discloses a method for synthesizing sucrose-6-ester under the catalytic action of lipase promoted by a constant magnetic field and belongs to the field of physical-field-assisted biocatalysis technology for organic synthesis. According to the invention, in a mixed solvent of non-aqueous medium dimethyl sulfoxide/tert-butyl (amyl) alcohol, the sucrose-6-ester is produced by reacting sucrose with fatty acid vinyl ester under catalytic action of lipase assisted by the constant magnetic field. The method is fast, efficient, simple and safe and is in line with the requirements of green chemistry.
Description
Technical field
The invention belongs to the technical field of the auxiliary biocatalysis of physical field, particularly a kind of permanent magnetic field promotes the method for lipase-catalyzed synthesis sucrose-6-ester.
Background technology
Sucrose-6-ester is the important intermediate of preparing Sucralose.Sucralose is in sucrose molecules 4, and 1 ', 6 '-OH is replaced by Cl atom, simultaneously 4-position there is configuration reversal and other-a kind of function sweeting agent that OH remains unchanged.And the order of 8-OH generation chlorination reaction is 6 in sucrose molecules, other positions of 6 ' >4>1 ' >, therefore before sucrose carries out chloridized, must first shield the 6-OH that reactive behavior is higher makes it not to be chlorinated, and then to 4,1 ', 6 '-OH carries out chloridized.So the 6-OH protection in sucrose molecules is the crucial prior step of chlorination reaction, must adopt 6-OH acylations method effectively.
It is two kinds of chemical processes that mainly adopt traditionally that ortho ester method and organotin catalysis method are prepared sucrose-6-ester.Ortho ester method is simple to operate, but yield is on the low side.On the contrary, organotin method yield is higher, but operates and last handling process complexity, and has the risk of heavy metals exceeding standard in product.
Due to advantages such as enzyme catalysis has that regioselectivity is strong, reaction conditions is gentle, simple to operate, environmental friendliness, security height, prepare in recent years sucrose-6-ester and more and more tend to utilize enzyme catalysis method.Find through large quantity research, proteolytic enzyme, lipase, abzyme are all the Major Enzymes for synthesis of sucrose ester.But the enzyme of different sources has catalysis feature and catalysis activity separately.1-OH or the 2-OH of the main catalysis sucrose of proteolytic enzyme, and conventionally do not accept longer chain fatty acid as acry radical donor.Compare proteolytic enzyme, lipase wide material sources, the fatty acid cane sugar ester of relative broad range all can catalyzedly synthesize, and reaction generally occurs in 6-OH.Utilize the synthetic purer sucrose-6-ester of abzyme catalysis sucrose also to studies confirm that recently, but still treat a dark step research.So mainly also refer to lipase for the enzyme that catalyzes and synthesizes sucrose-6-ester at present.
(the Ferrer M such as Ferrel; Cruces MA; Bernab ' e M, Ballesteros A, Plou FJ. Lipase-catalyzed regioselective acylation of sucrose in two-solvent mixtures. Biotechnol Bioeng 1999; 65:10 – 16) utilize H.lanuginosa lipase in nonaqueous phase DMSO/ tertiary amyl alcohol=1:4(volume ratio) catalysis sucrose reacts with vinyl laurate in mixing solutions, after 24h, sucrose inversion rate is 70%, the productive rate of sucrose-6-laurate is 40%.(the Luo Xu such as Luo Xu, Qian Junqing. lipase-catalyzed synthesis sucrose acetate [J] in trimethyl carbinol system. high chemical engineering journal, 2010,24 (3): 451-455) reacting the productive rate of cane sugar-6-acetic ester after 24 h with Lipozyme TL IM catalysis sucrose and vinyl-acetic ester is 40.9%.(king's Qing such as king's Qing, Zheng Pu, Ni Ye, Deng. the research of synthesizing cane sugar-6-acetic ester by using lipase for catalyzing [J] in non-aqueous media. food and fermentation industries. 2010,36 (12): 20-24) in DMSO/ trimethyl carbinol mixing solutions, utilize lipase-catalyzed sucrose and vinyl-acetic ester to generate cane sugar-6-acetic ester, reaction 9h, corresponding molar yield is 77%-89%.Although king's Qing etc. has improved the productive rate of cane sugar-6-acetic ester, relatively shortened the reaction times, but still exist the subject matters such as the reaction times is partially long.
Any material of occurring in nature all has magnetic, and the changing of magnetism just having is strong, a little less than some changing of magnetism; All have Anywhere magnetic field, just some places magnetic field is high, and some places magnetic field is low, and magnetic phenomenon is ubiquitous.Permanent magnetic field is the magnetic field that constant dc or stationary permanent magnet produce, and size and Orientation does not change in time.
For lipase, on the one hand, the action of a magnetic field may cause the part of enzyme molecule entirety conformation to be extended; On the other hand, the space structure of zymophore is maintained by less or weak secondary key, due to the strength of maintaining reactive site space structure a little less than, so easily affected by environment.The effect of external magnetic field, changes the space structure of enzyme, due to the flexibility of enzyme has occurred to change.This variation may make the active centre of enzyme more easily be exposed in oil-water termination, is conducive to the compound of reactive site and substrate, thereby improves the activity of enzyme.In addition, because enzyme has water-dredging head and hydrophilic tail simultaneously, the effect in magnetic field can be arranged in oil-water termination enzyme more in an orderly manner, this is also conducive to the absorption of solution contact surface to enzyme molecule, the enzyme molecule number that makes to be adsorbed on contact surface increases, due to the enzyme molecule number side of the establishment funtcional relationship of adsorbing on speed of response and solution contact surface, thus the speed of quickening enzymatic reaction.
(the Tao Weihua such as Tao Weihua, Wang Hongmin. the impact [J] of magnetic field on catalytic activity of lipase in organic solvent. the journal .2005 of Tianshui Normal University, 25 (2)) studied the impact of magnetic field on catalytic activity of lipase in organic solvent, pointed out that the magnetic field of 0.216T can make the ester synthesis of dynamic of porcine pancreatic lipase bring up to 39.7nmol/min.mg Pr by 24.8nmol/min.mg Pr.(the Zhang Qiuxia such as Zhang Qiuxia, Yin Chunling, Fan Qiuling, Zhu Yuanbao. the impact [J] of magnetic field on catalytic activity of lipase. the journal .2005 of tafelberg institute, 20 (5)) studied magnetic field to occurring in the impact of the enzymatic reaction on liquid-liquid two-phase interface, result shows 0. the action of a magnetic field 1 h of 1T can make enzyme activity raising 76.1% etc.They think that magnetic field is mainly the structure by affecting lipase, make enzyme active center that local trickle conformational change occur, thereby affect enzymatic reaction.
Summary of the invention
Goal of the invention: for the problem of prior art, the present invention adopts a kind of permanent magnetic field to promote the method for lipase-catalyzed synthesis sucrose-6-ester, has realized Reaction time shorten, has improved the object of the repeating utilization factor of enzyme.
Technical scheme: in order solving the problems of the technologies described above, to the invention provides a kind of method of permanent magnetic field promotion lipase-catalyzed synthesis sucrose-6-ester, to comprise the following steps:
1) by vacuum drying sucrose dissolved in the mixed solvent of nonaqueous phase methyl-sulphoxide and the trimethyl carbinol or tertiary amyl alcohol, add lipase and vinyl fatty ester to obtain reaction system, adopt permanent magnetic field to assist enzymatic mode, control temperature of reaction is 20-60 DEG C, the transformation efficiency of record reaction 0.5-10h;
2) after reaction finishes, lipase separates from mixed system by centrifugal, then with the trimethyl carbinol or tertiary amyl alcohol clean, vacuum-drying is for subsequent use;
3) liquid cooling after centrifugal, to room temperature, is revolved and is steamed the concentrated solution that obtains sucrose-6-ester.
Wherein, above-mentioned vinyl fatty ester comprises the one in vinyl-acetic ester, vinyl butyrate, sad vinyl acetate, capric acid vinyl acetate, vinyl laurate, palmitinic acid vinyl acetate or stearic acid vinyl ester.
Wherein, the volume ratio of above-mentioned methyl-sulphoxide and the trimethyl carbinol or tertiary amyl alcohol is 1:3-9.
Wherein, above-mentioned lipase add-on is 10-100mg/mL.
Wherein, the mol ratio of above-mentioned sucrose and vinyl fatty ester is 1:2-20.
Wherein, above-mentioned lipase is the one in Lipozyme TL IM, Lipozyme TL 100L or Lipozyme RM IM.
Wherein, the auxiliary enzymatic mode in above-mentioned permanent magnetic field is carried out catalyzed reaction or directly reacts in permanent magnetic field for first lipase being carried out to be placed in reaction system after the pre-treatment of permanent magnetic field again.
Wherein, above-mentioned first lipase to be carried out to the pretreated magnetic induction density in permanent magnetic field be 20-650mT, preferably 50-300mT; The time of pre-treatment lipase is 30-180min, preferably 40-100min.
Wherein, above-mentionedly directly in permanent magnetic field, react, magnetic induction density is 20-650mT, preferably 50-300mT.
Beneficial effect: the present invention is with respect to prior art, have the following advantages: the present invention adopts a kind of permanent magnetic field to assist lipase-catalyzed synthesis sucrose-6-ester, have and be swift in response, product purity is high, by product is few, simple to operate, safety, lipase can be by advantages such as repeated multiple times uses, meets the theory of Green Chemistry.The present invention adopts the auxiliary lipase-catalyzed sucrose in permanent magnetic field and vinyl fatty ester synthesis of sucrose-6-esters, and in the permanent magnetic field of suitable magneticstrength and magnetizing time, catalytic activity of lipase is improved, and main manifestations is significantly to shorten in the reaction times.
Embodiment
Below in conjunction with specific embodiment, further illustrate the present invention, but the invention is not restricted to this.
High performance liquid chromatography (HPLC) analysis condition: Shimadzu LC-10AT type high performance liquid chromatograph: LC-10AT high-pressure delivery pump, chromatographic column Supelcosil
tMlC-18 (250 × 4.6mm, 5um), 30 DEG C of column temperatures; Detector: RID-10A; Junctor: CBM-10A VP PLUS; Moving phase: acetonitrile/water=6/1(V/V); Sample size: 20 μ L, flow velocity 0.8mL/min.
Embodiment 1:
In the reactor of 100mL, first add the 0.9g sucrose having dissolved with 10mLDMSO, add successively again 30mL tertiary amyl alcohol, Lipozyme TL 100L 100mg/mL, the mol ratio of vinyl-acetic ester 0.5mL(sucrose and vinyl fatty ester is about 1:2), in the permanent magnetic field that is 20mT at magnetic induction density, react, 40 DEG C of temperature of reaction, stirring reaction 5h.Be heated to 80 DEG C and make lipase TL 100L inactivation, thus the centrifugal lipase of removing; Reaction product is cooled to room temperature, and underpressure distillation obtains cane sugar-6-acetic ester concentrated solution.HPLC analyzes to obtain the productive rate approximately 78.3% of cane sugar-6-acetic ester.
Embodiment 2:
By the sucrose dissolved after vacuum-drying in the mixed solvent of nonaqueous phase methyl-sulphoxide and the trimethyl carbinol, the volume ratio of methyl-sulphoxide and tertiary amyl alcohol is 1:5, then add Lipozyme RM IM 50mg/mL, add again capric acid vinyl acetate, the mol ratio that makes sucrose and capric acid vinyl acetate is 1:10, in the permanent magnetic field that is 50mT at magnetic induction density, react 4h at 50 DEG C.The centrifugal lipase of removing; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-certain herbaceous plants with big flowers acid esters concentrated solution.HPLC analyzes to such an extent that the productive rate of sucrose-6-decylate is about 80.1%.
Embodiment 3:
In the reactor of 100mL, first add the 0.6g sucrose having dissolved with 5mL DMSO, add successively again the mol ratio of the 45mL trimethyl carbinol, Lipozyme TL IM 10mg/mL, vinyl-acetic ester 3.2mL(sucrose and vinyl fatty ester to be about 1:20), 25 DEG C of reaction response temperature in the permanent magnetic field that is 300mT at magnetic induction density, stirring reaction 1h.Centrifugal, revolve after steaming to obtain weak yellow liquid.HPLC analyzes to obtain the productive rate approximately 80.3% of cane sugar-6-acetic ester.
Embodiment 4:
By dried sucrose dissolved, in the mixed solvent of nonaqueous phase methyl-sulphoxide and the trimethyl carbinol, the volume ratio of methyl-sulphoxide and the trimethyl carbinol is 1:4, is placed in water-bath constant temperature oscillator, rotating speed 300r/min, and 50 DEG C of constant temperature to sucrose dissolves completely; Then add Lipozyme TL IM 100mg/mL, the permanent magnetic field pre-treatment 40min that this enzyme has been 650mT with magnetic induction density; Add palmitinic acid vinyl acetate, the mol ratio that makes sucrose and palmitinic acid vinyl acetate is 1:15 again, controls 35 DEG C of waters temperature.After reaction 3h, the centrifugal lipase of removing; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-palm ester concentrated solution.HPLC analyzes to obtain the productive rate approximately 79.6% of sucrose-6-cetylate.
Embodiment 5:
By dried sucrose dissolved, in the mixed solvent of nonaqueous phase methyl-sulphoxide and tertiary amyl alcohol, the volume ratio of methyl-sulphoxide and tertiary amyl alcohol is 1:4, is placed in water-bath constant temperature oscillator, rotating speed 300r/min, and 50 DEG C of constant temperature to sucrose dissolves completely; Then add Lipozyme TL IM 100mg/mL, the permanent magnetic field pre-treatment 100min that this enzyme has been 175mT with magnetic induction density; Add vinyl laurate, the mol ratio that makes sucrose and vinyl laurate is 1:18 again, controls 35 DEG C of waters temperature.After reaction 3h, the centrifugal lipase of removing; Reaction product is cooled to room temperature, and underpressure distillation obtains sucrose-6-lauryl concentrated solution.HPLC analyzes to obtain the productive rate approximately 88.9% of sucrose-6-laurate.
Embodiment 6:
In the reactor of 50mL, first add the 0.1g sucrose having dissolved with 1mL DMSO, add successively again the mol ratio of the 4mL trimethyl carbinol, Lipozyme TL IM 100mg/mL, vinyl-acetic ester 0.5mL(sucrose and vinyl fatty ester to be about 1:20), in the permanent magnetic field that is 230mT at magnetic induction density, react, 35 DEG C of temperature of reaction, stirring reaction 3.5h.Centrifugal, revolve after steaming to obtain weak yellow liquid.HPLC analyzes to obtain the productive rate approximately 90.7% of cane sugar-6-acetic ester.
The above is only the preferred embodiment of the present invention; be noted that for those skilled in the art; under the premise without departing from the principles of the invention, can also make some improvements and modifications, these improvements and modifications also should be considered as protection scope of the present invention.
Claims (9)
1. permanent magnetic field promotes a method for lipase-catalyzed synthesis sucrose-6-ester, it is characterized in that, comprises the following steps:
1) by vacuum drying sucrose dissolved in the mixed solvent of nonaqueous phase methyl-sulphoxide and the trimethyl carbinol or tertiary amyl alcohol, add lipase and vinyl fatty ester to obtain reaction system, adopt permanent magnetic field to assist enzymatic mode, control temperature of reaction is 20-60 DEG C, the transformation efficiency of record reaction 0.5-10h;
2) after reaction finishes, lipase separates from mixed system by centrifugal, then with the trimethyl carbinol or tertiary amyl alcohol clean, vacuum-drying is for subsequent use;
3) liquid cooling after centrifugal, to room temperature, is revolved and is steamed the concentrated solution that obtains sucrose-6-ester.
2. permanent magnetic field according to claim 1 promotes the method for lipase-catalyzed synthesis sucrose-6-ester, it is characterized in that, described vinyl fatty ester comprises the one in vinyl-acetic ester, vinyl butyrate, sad vinyl acetate, capric acid vinyl acetate, vinyl laurate, palmitinic acid vinyl acetate or stearic acid vinyl ester.
3. permanent magnetic field according to claim 1 promotes the method for auxiliary lipase-catalyzed synthesis sucrose-6-ester, it is characterized in that, the volume ratio of described methyl-sulphoxide and the trimethyl carbinol or tertiary amyl alcohol is 1:3-9.
4. permanent magnetic field according to claim 1 promotes the method for lipase-catalyzed synthesis sucrose-6-ester, it is characterized in that, described lipase add-on is 10-100mg/mL.
5. permanent magnetic field according to claim 1 promotes the method for lipase-catalyzed synthesis sucrose-6-ester, it is characterized in that, the mol ratio of described sucrose and vinyl fatty ester is 1:2-20.
6. permanent magnetic field according to claim 1 promotes the method for lipase-catalyzed synthesis sucrose-6-ester, it is characterized in that, described lipase is the one in Lipozyme TL IM, Lipozyme TL 100L or Lipozyme RM IM.
7. permanent magnetic field according to claim 1 promotes the method for lipase-catalyzed synthesis sucrose-6-ester, it is characterized in that, the auxiliary enzymatic mode in described permanent magnetic field is carried out catalyzed reaction or directly reacts in permanent magnetic field for first lipase being carried out to be placed in reaction system after the pre-treatment of permanent magnetic field again.
8. permanent magnetic field according to claim 7 promotes the method for lipase-catalyzed synthesis sucrose-6-ester, it is characterized in that, described first lipase to be carried out to the pretreated magnetic induction density in permanent magnetic field be 20-650mT, and the time of pre-treatment lipase is 30-180min.
9. permanent magnetic field according to claim 1 promotes the method for lipase-catalyzed synthesis sucrose-6-ester, it is characterized in that, describedly directly in permanent magnetic field, reacts, and magnetic induction density is 20-650mT.
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| CN111560408A (en) * | 2020-02-29 | 2020-08-21 | 浙江工业大学 | Method for synthesizing coumarin-3-carboxylic acid sugar ester derivative on line based on flow chemistry enzymatic catalysis |
| CN112080531A (en) * | 2020-09-02 | 2020-12-15 | 山东吉青化工有限公司 | Preparation method of pentaerythritol monocarboxylic ester plasticizer and application of pentaerythritol monocarboxylic ester plasticizer in medical PVC (polyvinyl chloride) products |
| CN112280817A (en) * | 2020-10-28 | 2021-01-29 | 江苏科鼐生物制品有限公司 | Method for synthesizing soyasterol oleate by catalyzing enzyme through magnetic induction electric field |
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| CN112080531B (en) * | 2020-09-02 | 2023-08-08 | 山东吉青化工有限公司 | Preparation method of pentaerythritol monocarboxylic ester plasticizer and application of plasticizer in medical PVC (polyvinyl chloride) product |
| CN112280817A (en) * | 2020-10-28 | 2021-01-29 | 江苏科鼐生物制品有限公司 | Method for synthesizing soyasterol oleate by catalyzing enzyme through magnetic induction electric field |
| CN112280817B (en) * | 2020-10-28 | 2022-07-29 | 江苏科鼐生物制品有限公司 | Method for synthesizing soyasterol oleate by catalyzing enzyme through magnetic induction electric field |
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Application publication date: 20140910 |