CN105237420A - Novel L-threonine synthetic process - Google Patents
Novel L-threonine synthetic process Download PDFInfo
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- CN105237420A CN105237420A CN201510760098.5A CN201510760098A CN105237420A CN 105237420 A CN105237420 A CN 105237420A CN 201510760098 A CN201510760098 A CN 201510760098A CN 105237420 A CN105237420 A CN 105237420A
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- threonine
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Abstract
The invention discloses a novel L-threonine synthetic process. According to the process, CH2CHCH(OH)CH3(3-butene-2-alcohol) is taken as the raw material, Cu2(OH)2CO3 and CuC12 are taken as catalysts, double bonds react with phCONCO after being epoxidized under the action of the catalysts to generate a five-membered heterocyclic compound, acidification loop opening is conducted to generate DL-threonine, and separation is conducted to obtain L-threonine. The process is easy to operate, Cu2(OH)2CO3 and CuC12 are added to serve as catalysts under research on the basis that the original process conditions are unchanged, the utilization rate of raw materials is increased greatly, raw material cost is effectively reduced, the yield of L-threonine is increased to 83% and is far higher than that of the existing process, and large-scale production is guaranteed for enterprises.
Description
Technical field
The invention belongs to technical field of compound preparation, particularly relate to a kind of L-threonine new synthetic process.
Background technology
L-threonine is a kind of necessary amino acid, is mainly used in the aspects such as medicine, chemical reagent, food fortifier, fodder additives.In medicine industry, L-threonine can be used for configuration amino acid transfusion and comprehensive amino acid preparation, its molysite also can be used for anti-anemia action medicine, L-threonine also has promotion human development and lipotropic medicinal curative effect simultaneously, it is the intermediate manufacturing efficient microbiotic monobactam, and for Biochemical Research clinically, L-threonine has the function improving immunity.
At present, all there is the report of L-threonine new synthetic process at home and abroad, comprise biological synthesis process, proteolysis method and chemical synthesis.Wherein, biological synthesis process comprises direct fermentation and enzyme transforming process two kinds, and the advantage of enzyme transforming process is that specificity is high, product is single, is easy to refining, is paid attention to very much in recent years.But the report of Production by Enzymes L-threonine is also few.Direct fermentation produces L-threonine, pantonine-the hydroxypentanoic acid (AHV) of usual employing brevibacterium sp bacterium and S-(2-amino-ethyl)-Cys (AEC) Double-resistant variant its require all higher to the throughput of bacterial classification and fermentation equipment and fermentation condition, thus produce and be often restricted.
Proteolysis method is for raw material with natural proteins such as blood meal, angle hoof, corn gluten meal, cottonseed cake and silk gum, first carry out washing and blend, after drying, again by acid, alkali or these natural proteins of enzymic hydrolysis, after its hydrolyzed solution is condensed to concentrated solution, have two kinds of methods to be separated and obtain Threonine: a kind of method be in butenoic acid with the methanol solution effect of smelling, carry out amination with ammonia again, obtain through ion exchange resin separation and purification; Another kind method activated carbon decolorizing, upper prop, receiving liquid makes paper chromatography, collects Threonine.Because Threonine content in these protein is lower, when extracting Threonine, other amino acid is fallen by as soil fertility quality simultaneously, and in addition, this kind of preparation method's operating process is complicated, need process a large amount of elutriants, waste resource, therefore application at present is less.
Biological synthesis process comprises asymmetric Epoxidation method and glycocoll-copper method, and asymmetric Epoxidation method is with CH
2cHCH (OH) CH
3for raw material, double bond, after epoxidation, is reacted with phCONCO, generates five member ring heterocyclic compound, then acidifying open loop, generates DL-Threonine, then carries out fractionation and obtain L-threonine.Glycocoll-copper method is the main method of current Threonine chemosynthesis, i.e. glycine → glycocoll-copper → copper-threonine → DL-Threonine, then by racemase or preferential crystallization method, DL-Threonine is converted into L-threonine.The shortcoming of these two kinds of methods is that productive rate is low, is difficult to realize suitability for industrialized production.
Summary of the invention
In order to overcome the defect of prior art, the object of the present invention is to provide a kind of L-threonine new synthetic process, easy and simple to handle, productive rate is high, is suitable for suitability for industrialized production.
L-threonine new synthetic process, with CH
2cHCH (OH) CH
3(3-butene-2-ol) is raw material, Cu
2(OH)
2cO
3and CuC
12for catalyzer, double bond, after epoxidation, under the effect of catalyzer, is reacted with phCONCO, generates five member ring heterocyclic compound, then acidifying open loop, generates DL-Threonine, then carries out fractionation and obtain L-threonine.
The present invention improves further, and the mass ratio of described raw material and catalyzer is 100:0.05-0.2.
The present invention improves further, described Cu
2(OH)
2cO
3with CuC
12mass ratio be 1:0.8-1.2.
The present invention improves further, also comprises step: after diluting soln, filtering and removing Cu
2(OH)
2cO
3and CuC
12catalyzer.
The present invention improves further, described Cu
2(OH)
2cO
3purity be more than 99.5%.
The present invention improves further, described CuC
12purity be more than 99.5%.
Present invention process is easy and simple to handle, on the basis not changing original processing condition, is added by research with Cu
2(OH)
2cO
3and CuC
12for catalyzer, substantially increase the utilization ratio of raw material, effectively reduce raw materials cost, the productive rate of L-threonine is brought up to 83% simultaneously, far away the high productive rate having technique, for the large-scale production of enterprise provides guarantee.
Embodiment
Below in conjunction with embodiment to the present invention's row detailed description further.
Embodiment 1
L-threonine new synthetic process, with CH
2cHCH (OH) CH
3(3-butene-2-ol) is raw material, Cu
2(OH)
2cO
3and CuC
12for catalyzer, double bond, after epoxidation, under the effect of catalyzer, is reacted with phCONCO, generates five member ring heterocyclic compound, after diluting soln, and filtering and removing Cu
2(OH)
2cO
3and CuC
12catalyzer, then acidifying open loop, generate DL-Threonine, then carry out fractionation and obtain L-threonine.
Wherein preferred, the mass ratio of described raw material and catalyzer is 100:0.2.
Wherein preferred, described Cu
2(OH)
2cO
3with CuC
12mass ratio be 1:1.
Wherein preferred, described Cu
2(OH)
2cO
3purity be 99.9%.
Wherein preferred, described CuC
12purity be 99.9%.
The productive rate of the L-threonine of the present embodiment is in table 1.
Embodiment 2
Concrete steps are as embodiment 1, and wherein preferably, the mass ratio of described raw material and catalyzer is 100:0.1.Described Cu
2(OH)
2cO
3with CuC
12mass ratio be 1:1.2.Described Cu
2(OH)
2cO
3purity be 99.5%, described CuC
12purity be 99.5%.The productive rate of the L-threonine of the present embodiment is in table 1.
Embodiment 3
Concrete steps are as embodiment 1, and wherein preferably, the mass ratio of described raw material and catalyzer is 100:0.05.Described Cu
2(OH)
2cO
3with CuC
12mass ratio be 1:0.8.Described Cu
2(OH)
2cO
3purity be 99.9%, described CuC
12purity be 99.9%.The productive rate of the L-threonine of the present embodiment is in table 1.
Embodiment 4
Concrete steps are as embodiment 1, and wherein preferably, the mass ratio of described raw material and catalyzer is 100:0.2.Described Cu
2(OH)
2cO
3with CuC
12mass ratio be 1:0.8.Described Cu
2(OH)
2cO
3purity be 99.5%, described CuC
12purity be 99.5%.The productive rate of the L-threonine of the present embodiment is in table 1.
Embodiment 5
Concrete steps are as embodiment 1, and wherein preferably, the mass ratio of described raw material and catalyzer is 100:0.1.Described Cu
2(OH)
2cO
3with CuC
12mass ratio be 1:1.Described Cu
2(OH)
2cO
3purity be 99.9%, described CuC
12purity be 99.9%.The productive rate of the L-threonine of the present embodiment is in table 1.
The productive rate of table 1L-Threonine
| Project | Productive rate |
| Embodiment 1 | 83.56％ |
| Embodiment 2 | 82.97％ |
| Embodiment 3 | 83.14％ |
| Embodiment 4 | 83.27％ |
| Embodiment 5 | 83.02％ |
Learnt by above-mentioned data, the present invention, on the basis not changing original processing condition, is added by research with Cu
2(OH)
2cO
3and CuC
12for catalyzer, the productive rate of L-threonine is brought up to 83%, substantially increase the utilization ratio of raw material, effectively reduce raw materials cost.
Claims (7)
1.L-Threonine new synthetic process, is characterized in that, with CH
2cHCH (OH) CH
3for raw material, Cu
2(OH)
2cO
3and CuC
12for catalyzer.
2. L-threonine new synthetic process according to claim 1, is characterized in that, this technique comprises following concrete steps: CH
2cHCH (OH) CH
3double bond, after epoxidation, under catalyst action, is reacted with phCONCO, generates five member ring heterocyclic compound, then acidifying open loop, generates DL-Threonine, then carries out fractionation and obtain L-threonine.
3. L-threonine new synthetic process according to claim 1, is characterized in that, the mass ratio of described raw material and catalyzer is 100:0.05-0.2.
4. L-threonine new synthetic process according to claim 1, is characterized in that, described Cu
2(OH)
2cO
3with CuC
12mass ratio be 1:0.8-1.2.
5. L-threonine new synthetic process according to claim 2, is characterized in that, also comprise step: after diluting soln, filtering and removing Cu
2(OH)
2cO
3and CuC
12catalyzer.
6. L-threonine new synthetic process according to claim 1, is characterized in that, described Cu
2(OH)
2cO
3purity be more than 99.5%.
7. L-threonine new synthetic process according to claim 1, is characterized in that, described CuC
12purity be more than 99.5%.
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|---|---|---|---|
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| CN201510760098.5A CN105237420B (en) | 2015-11-06 | 2015-11-06 | L threonine synthesis techniques |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130001011A (en) * | 2011-06-24 | 2013-01-03 | 장흥군 | Gochujang process using hovenia dulcis thunb. and the gochujang thereof |
| CN103232370A (en) * | 2013-05-09 | 2013-08-07 | 成都郑源生化科技有限公司 | Preparation method of fmoc chloride glutamic acid-4-tert-butyl ester |
| CN104769119A (en) * | 2012-06-15 | 2015-07-08 | 英威达技术有限责任公司 | Methods for biosynthesizing 1,3 butadiene |
-
2015
- 2015-11-06 CN CN201510760098.5A patent/CN105237420B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130001011A (en) * | 2011-06-24 | 2013-01-03 | 장흥군 | Gochujang process using hovenia dulcis thunb. and the gochujang thereof |
| CN104769119A (en) * | 2012-06-15 | 2015-07-08 | 英威达技术有限责任公司 | Methods for biosynthesizing 1,3 butadiene |
| CN103232370A (en) * | 2013-05-09 | 2013-08-07 | 成都郑源生化科技有限公司 | Preparation method of fmoc chloride glutamic acid-4-tert-butyl ester |
Non-Patent Citations (1)
| Title |
|---|
| MICHAELE. JUNG ET AL.: "Rapid synthesis of b-hydroxy-a-amino acids, such as L-threonine, b-hydroxyphenylalanine, and β-hydroxyleucine, via an application of the Sharpless asymmetric epoxidation", 《TETRAHEDRON LETTERS》 * |
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Effective date of registration: 20210924 Address after: 210033 9th floor, F6 building, No.9, Weidi Road, Qixia District, Nanjing City, Jiangsu Province Patentee after: SKYRUN PHARMA Co.,Ltd. Address before: 238251 fine chemical base of Wujiang Town, he County, Ma'anshan City, Anhui Province Patentee before: FARMASINO PHARMACEUTICAL (ANHUI) Co.,Ltd. |