CN107365812A - A kind of Enzyme catalyzed synthesis technique of 5 ' cytidine monophosphate - Google Patents
A kind of Enzyme catalyzed synthesis technique of 5 ' cytidine monophosphate Download PDFInfo
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- CN107365812A CN107365812A CN201710615002.5A CN201710615002A CN107365812A CN 107365812 A CN107365812 A CN 107365812A CN 201710615002 A CN201710615002 A CN 201710615002A CN 107365812 A CN107365812 A CN 107365812A
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Abstract
The invention discloses a kind of Enzyme catalyzed synthesis technique of 5 ' cytidine monophosphate, comprise the following steps：The synthesis of cytidine：Cytimidine synthesizes cytidine with D ribose under the catalytic action of synzyme I, and reaction resulting solution is carried out being filtrated to get cytidine filtered fluid；The preparation of 5 ' cytidine acid mother liquors：Cytidine filtered fluid neutralising phosphoric acid sodium dihydrogen synthesizes 5 ' cytidine monophosphates under the catalytic action of synthetase II, and gained reaction solution insulated and stirred is filtrated to get 5 ' cytidine acid mother liquors afterwards for a period of time；The essence of 5 ' cytidine monophosphates carries：The pH of 5 ' cytidine acid mother liquors is adjusted, 5 ' cytidine acid crudes is then filtrated to get, 5 ' cytidine monophosphate crude product refinings is obtained into the cytidine monophosphate of product 5 '.It is an advantage of the invention that：The production cost of 5 ' cytidine monophosphates can be reduced；Process cycle is shorter, can improve the preparation efficiency of 5 ' cytidine monophosphates；The total recovery of the cytidine monophosphate of product 5 ' reaches more than 90%, and content is more than 99%；It is harmless to environment, equipment and operating personnel.
Description
Technical field
The present invention relates to biological chemical field, and in particular to a kind of Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate.
Background technology
5'-CMP is the intracellular important biochemical substances of biology, participates in a variety of biochemical reactions.Industrially, 5 '-born of the same parents
Thuja acid is mainly for the manufacture of medicines such as CDPC, cytidine triphosphate (CTP), cytarabine, poly ICs.In recent years, also can with it is other
Nucleotides coordinates in addition milk powder, to strengthen the immunity of baby.
5'-CMP mainly has two kinds of modes of production, and 1）From RNA（Ribonucleic acid）Degraded, is then isolated to；2）From
Cytidine is set out, and phosphoric acid group is connected in its 5 ' position with chemical method, forms 5'-CMP.Although first method can once obtain
To four kinds of products, but in addition to cytidine monophosphate, other three kinds turn into accessory substance, furthermore RNA sources be restricted it is more and raw
Lock out operation is complicated in production. art, and yield is low；Industrial synthesis 5'-CMP mainly uses chemical method at present, and this method is main
Shortcoming is cost of material height, and the three wastes are more, etching apparatus and are unfavorable for personnel's health and industrialized production.
The content of the invention
To solve the above problems, the invention provides a kind of Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate, the synthesis technique with
Cytimidine, D-ribose and sodium dihydrogen phosphate are raw material, are reacted in the presence of synzyme and obtain 5 '-cytidine monophosphate, required raw material comes
Source is extensive, cheap, and course of reaction is gentle, will not produce unfavorable factor to consersion unit and operating personnel.
The technical solution adopted by the present invention is：
A kind of Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate, comprises the following steps：
A, the synthesis of cytidine：Cytimidine and D-ribose are added in pure water, adjust temperature and pH, then adds synzyme I, born of the same parents
Pyrimidine catalyzes and synthesizes cytidine with D-ribose in the presence of synzyme I, and the reaction is composed when detection cytimidine disappears in liquid and terminated, instead
Reaction resulting solution is carried out being filtrated to get cytidine filtered fluid after should terminating；
B, the preparation of 5 '-cytidine acid mother liquor：Synthetase II and sodium dihydrogen phosphate are added into cytidine filtered fluid, adjust temperature and
PH, cytidine filtered fluid and sodium dihydrogen phosphate catalyze and synthesize 5 '-cytidine monophosphate in the presence of synthetase II, and liquid spectrum detection cytidine disappears
When reaction terminating, gained reaction solution insulated and stirred is filtrated to get 5 '-cytidine acid mother liquor afterwards for a period of time；
C, the essence of 5 '-cytidine monophosphate carries：The pH of 5 '-cytidine acid mother liquor is directly adjusted, is then filtrated to get 5 '-cytidine acid crude, will
5 '-cytidine monophosphate crude product refining obtains product 5 '-cytidine monophosphate.
Further, the step a, temperature is in the preparation of synthetic reaction and step b5 '-cytidine acid mother liquor of cytidine
37-39 DEG C, pH is 6.7-7.0.
Further, the dosage of the synzyme I is 0.5-1.0 times of the cytimidine dosage, the synthetase II
Dosage is 1.0-2.0 times of the cytimidine dosage.
Further, the step b, reaction solution need to stir in 45 DEG C of insulations described in the preparation reaction of 5 '-cytidine acid mother liquor
Mix 1-3 hours.
Further, the step c, the pH to 1- of 5 '-cytidine acid mother liquor is adjusted in the preparation process of 5 '-cytidine monophosphate
3。
Further, the total recovery of the 5 '-cytidine monophosphate reaches more than 90%, and purity is more than 99%.
Further, need to add a small amount of PEG400 in the step a as phase transfer catalyst.
Further, the dosage of the cytimidine, D-ribose, PEG400, sodium dihydrogen phosphate and pure water is in parts by weight：Born of the same parents
600 parts of 111.10 parts of pyrimidine, 150.13 parts of D-ribose, 0.11 part of PEG400,240 parts of sodium dihydrogen phosphate and pure water.
Further, the synzyme I includes cytidine ligase and NAD+, and the content of the NAD+ connects for the cytidine
The 0.01%-0.02% of enzyme content, the synthetase II include cytidine kinases and ATP, and the content of the ATP is the cytidine kinases
The 0.1%-0.5% of content.
The beneficial effects of the invention are as follows：1st, required raw material cytimidine, D-ribose and sodium dihydrogen phosphate wide material sources, price be just
Preferably, required synzyme reusable edible, thus the production cost of 5 '-cytidine monophosphate can be substantially reduced；2nd, only need two enzymatics anti-
Step should being put forward with an essence and can obtain product 5 '-cytidine monophosphate, process cycle is shorter, can effectively improve the preparation of 5 '-cytidine monophosphate
Efficiency；3rd, the total recovery of product 5 '-cytidine monophosphate reaches more than 90%, and content is more than 99%, and enzymic catalytic reaction effect substantially increases
Transformation efficiency；4th, enzymic catalytic reaction course of reaction is more gentle, harmless to environment, equipment and operating personnel.
Embodiment
In order to deepen the understanding of the present invention, below in conjunction with embodiment, the invention will be further described, the embodiment
It is only used for explaining the present invention, does not form the restriction to protection scope of the present invention.
Embodiment 1
A, the synthesis of cytidine：Take 1000ml four-hole boiling flasks, add 111.10g cytimidines, 150.13gD- ribose, 600g pure water and
0.11g PEG400, the temperature of stirring and regulating thermostatic agitator in four-hole boiling flask fixed placement to thermostatic mixer, will be started
To 37-39 DEG C, the pH of mixed liquor in four-hole boiling flask is adjusted to 6.7, and adds 55.6g synzyme I in backward four-hole boiling flask, synthesis
The content that enzyme I includes cytidine ligase and NAD+, NAD+ is the 0.01%-0.02% of cytidine ligase content, insulated and stirred, often
Sample is taken out from four-hole boiling flask every other hour and carries out liquid spectrum analysis, when liquid, which composes detection cytimidine, to be reacted away completely, reaction is eventually
Only, resulting solution will be reacted in four-hole boiling flask to be filtered, filter cake is rinsed with 200g pure water, by gained filtrate and rinsing liquid
Merge, as cytidine filtered fluid；
B, the preparation of 5 '-cytidine acid mother liquor：1000ml four-hole boiling flasks are cleaned, pour into cytidine filtered fluid obtained by step a, fixation is put
To put on thermostatic mixer, regulating thermostatic agitator temperature adds 240g sodium dihydrogen phosphates into four-hole boiling flask to 37-39 DEG C,
Stirring and dissolving, the liquid pH to 6.7 in four-hole boiling flask is adjusted, then add 111g synthetase IIs, synthetase II swashs including cytidine
Enzyme and ATP, ATP content are the 0.1%-0.5% of cytidine kinases content, and insulated and stirred is every to be taken every other hour from four-hole boiling flask
Go out sample and carry out liquid spectrum analysis, when liquid, which composes detection cytidine, to be reacted away completely, reaction terminating, regulating thermostatic agitator temperature to 45
DEG C, insulated and stirred 1 hour, the reaction solution in four-hole boiling flask is filtered, filter cake is rinsed with 200g pure water, and gained is filtered
Liquid and rinsing liquid merge, as 5 '-cytidine acid mother liquor；
C, the essence of 5 '-cytidine monophosphate carries：The pH to 2.5 of 5 '-cytidine acid mother liquor obtained by regulating step b, 0 DEG C is cooled to, insulation one is small
When, 306.5g 5 '-cytidine acid crude is filtrated to get, 292.1g 5 '-cytidine monophosphates of product are obtained after re-refining.
The yield of product 5 '-cytidine monophosphate is 90.38%, content 99.21%.
Embodiment 2
A, the synthesis of cytidine：Take 1000ml four-hole boiling flasks, add 111.10g cytimidines, 150.13gD- ribose, 600g pure water and
0.11g PEG400, the temperature of stirring and regulating thermostatic agitator in four-hole boiling flask fixed placement to thermostatic mixer, will be started
To 37-39 DEG C, the pH of mixed liquor in four-hole boiling flask is adjusted to 7.0, and adds 55.6g synzyme I in backward four-hole boiling flask, synthesis
The content that enzyme I includes cytidine ligase and NAD+, NAD+ is the 0.01%-0.02% of cytidine ligase content, insulated and stirred, often
Sample is taken out from four-hole boiling flask every other hour and carries out liquid spectrum analysis, when liquid, which composes detection cytimidine, to be reacted away completely, reaction is eventually
Only, resulting solution will be reacted in four-hole boiling flask to be filtered, filter cake is rinsed with 200g pure water, by gained filtrate and rinsing liquid
Merge, as cytidine filtered fluid；
B, the preparation of 5 '-cytidine acid mother liquor：1000ml four-hole boiling flasks are cleaned, pour into cytidine filtered fluid obtained by step a, fixation is put
To put on thermostatic mixer, regulating thermostatic agitator temperature adds 240g sodium dihydrogen phosphates into four-hole boiling flask to 37-39 DEG C,
Stirring and dissolving, the liquid pH to 7.0 in four-hole boiling flask is adjusted, then add 111g synthetase IIs, synthetase II swashs including cytidine
Enzyme and ATP, ATP content are the 0.1%-0.5% of cytidine kinases content, and insulated and stirred is every to be taken every other hour from four-hole boiling flask
Go out sample and carry out liquid spectrum analysis, when liquid, which composes detection cytidine, to be reacted away completely, reaction terminating, regulating thermostatic agitator temperature to 45
DEG C, insulated and stirred 1 hour, the reaction solution in four-hole boiling flask is filtered, filter cake is rinsed with 200g pure water, and gained is filtered
Liquid and rinsing liquid merge, as 5 '-cytidine acid mother liquor；
C, the essence of 5 '-cytidine monophosphate carries：The pH to 2.5 of 5 '-cytidine acid mother liquor obtained by regulating step b, 0 DEG C is cooled to, insulation one is small
When, 306.7g 5 '-cytidine acid crude is filtrated to get, 287.16g 5 '-cytidine monophosphates of product are obtained after re-refining.
The yield of product 5 '-cytidine monophosphate is 90.07%, content 99.21%.
Embodiment 3
A, the synthesis of cytidine：Take 1000ml four-hole boiling flasks, add 111.10g cytimidines, 150.13gD- ribose, 600g pure water and
0.11g PEG400, the temperature of stirring and regulating thermostatic agitator in four-hole boiling flask fixed placement to thermostatic mixer, will be started
To 37-39 DEG C, the pH of mixed liquor in four-hole boiling flask is adjusted to 6.7, and adds 111.1g synzyme I in backward four-hole boiling flask, is closed
Into enzyme I include cytidine ligase and NAD+, NAD+ content be cytidine ligase content 0.01%-0.02%, insulated and stirred,
Liquid spectrum analysis is carried out per sample is taken out from four-hole boiling flask every other hour, when liquid, which composes detection cytimidine, to be reacted away completely, reaction
Terminate, filtered resulting solution is reacted in four-hole boiling flask, filter cake is rinsed with 200g pure water, by gained filtrate and rinsing
Liquid merges, as cytidine filtered fluid；
B, the preparation of 5 '-cytidine acid mother liquor：1000ml four-hole boiling flasks are cleaned, pour into cytidine filtered fluid obtained by step a, fixation is put
To put on thermostatic mixer, regulating thermostatic agitator temperature adds 240g sodium dihydrogen phosphates into four-hole boiling flask to 37-39 DEG C,
Stirring and dissolving, the liquid pH to 6.7 in four-hole boiling flask is adjusted, then add 222g synthetase IIs, synthetase II swashs including cytidine
Enzyme and ATP, ATP content are the 0.1%-0.5% of cytidine kinases content, and insulated and stirred is every to be taken every other hour from four-hole boiling flask
Go out sample and carry out liquid spectrum analysis, when liquid, which composes detection cytidine, to be reacted away completely, reaction terminating, regulating thermostatic agitator temperature to 45
DEG C, insulated and stirred 1 hour, the reaction solution in four-hole boiling flask is filtered, filter cake is rinsed with 200g pure water, and gained is filtered
Liquid and rinsing liquid merge, as 5 '-cytidine acid mother liquor；
C, the essence of 5 '-cytidine monophosphate carries：The pH to 2.5 of 5 '-cytidine acid mother liquor obtained by regulating step b, 0 DEG C is cooled to, insulation one is small
When, 307.55g 5 '-cytidine acid crude is filtrated to get, 293.22g 5 '-cytidine monophosphates of product are obtained after re-refining.
The yield of product 5 '-cytidine monophosphate is 90.74%, content 99.12%.
Embodiment 4
A, the synthesis of cytidine：Take 1000ml four-hole boiling flasks, add 111.10g cytimidines, 150.13gD- ribose, 600g pure water and
0.11g PEG400, the temperature of stirring and regulating thermostatic agitator in four-hole boiling flask fixed placement to thermostatic mixer, will be started
To 37-39 DEG C, the pH of mixed liquor in four-hole boiling flask is adjusted to 7.0, and adds 111.1g synzyme I in backward four-hole boiling flask, is closed
Into enzyme I include cytidine ligase and NAD+, NAD+ content be cytidine ligase content 0.01%-0.02%, insulated and stirred,
Liquid spectrum analysis is carried out per sample is taken out from four-hole boiling flask every other hour, when liquid, which composes detection cytimidine, to be reacted away completely, reaction
Terminate, filtered resulting solution is reacted in four-hole boiling flask, filter cake is rinsed with 200g pure water, by gained filtrate and rinsing
Liquid merges, as cytidine filtered fluid；
B, the preparation of 5 '-cytidine acid mother liquor：1000ml four-hole boiling flasks are cleaned, pour into cytidine filtered fluid obtained by step a, fixation is put
To put on thermostatic mixer, regulating thermostatic agitator temperature adds 240g sodium dihydrogen phosphates into four-hole boiling flask to 37-39 DEG C,
Stirring and dissolving, the liquid pH to 7.0 in four-hole boiling flask is adjusted, then add 222g synthetase IIs, synthetase II swashs including cytidine
Enzyme and ATP, ATP content are the 0.1%-0.5% of cytidine kinases content, and insulated and stirred is every to be taken every other hour from four-hole boiling flask
Go out sample and carry out liquid spectrum analysis, when liquid, which composes detection cytidine, to be reacted away completely, reaction terminating, regulating thermostatic agitator temperature to 45
DEG C, insulated and stirred 1 hour, the reaction solution in four-hole boiling flask is filtered, filter cake is rinsed with 200g pure water, and gained is filtered
Liquid and rinsing liquid merge, as 5 '-cytidine acid mother liquor；
C, the essence of 5 '-cytidine monophosphate carries：The pH to 2.5 of 5 '-cytidine acid mother liquor obtained by regulating step b, 0 DEG C is cooled to, insulation one is small
When, 306.98g 5 '-cytidine acid crude is filtrated to get, 290.31g 5 '-cytidine monophosphates of product are obtained after re-refining.
The yield of product 5 '-cytidine monophosphate is 90.13%, content 99.19%.
Claims (9)
1. the Enzyme catalyzed synthesis technique of a kind of 5 '-cytidine monophosphate, it is characterised in that comprise the following steps：
A, the synthesis of cytidine：Cytimidine and D-ribose are added in pure water, adjust temperature and pH, then adds synzyme I, born of the same parents
Pyrimidine catalyzes and synthesizes cytidine with D-ribose in the presence of synzyme I, and the reaction is composed when detection cytimidine disappears in liquid and terminated, instead
Reaction resulting solution is carried out being filtrated to get cytidine filtered fluid after should terminating；
B, the preparation of 5 '-cytidine acid mother liquor：Synthetase II and sodium dihydrogen phosphate are added into cytidine filtered fluid, adjust temperature and
PH, cytidine filtered fluid and sodium dihydrogen phosphate catalyze and synthesize 5 '-cytidine monophosphate in the presence of synthetase II, and liquid spectrum detection cytidine disappears
When reaction terminating, gained reaction solution insulated and stirred is filtrated to get 5 '-cytidine acid mother liquor afterwards for a period of time；
C, the essence of 5 '-cytidine monophosphate carries：The pH of 5 '-cytidine acid mother liquor is directly adjusted, is then filtrated to get 5 '-cytidine acid crude, will
5 '-cytidine monophosphate crude product refining obtains product 5 '-cytidine monophosphate.
A kind of 2. Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate according to claim 1, it is characterised in that the step a,
Temperature is 37-39 DEG C in the preparation of synthetic reaction and step b5 '-cytidine acid mother liquor of cytidine, and pH is 6.7-7.0.
A kind of 3. Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate according to claim 1, it is characterised in that the synzyme I
Dosage be 0.5-1.0 times of the cytimidine dosage, the dosage of the synthetase II for the cytimidine dosage 1.0-2.0
Times.
A kind of 4. Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate according to claim 1, it is characterised in that the step b,
Reaction solution need to be in 45 DEG C of insulated and stirred 1-3 hours described in the preparation reaction of 5 '-cytidine acid mother liquor.
A kind of 5. Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate according to claim 1, it is characterised in that the step c,
The pH to 1-3 of 5 '-cytidine acid mother liquor is adjusted in the preparation process of 5 '-cytidine monophosphate.
A kind of 6. Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate according to claim 1, it is characterised in that the 5 '-born of the same parents
The total recovery of thuja acid reaches more than 90%, and purity is more than 99%.
7. the Enzyme catalyzed synthesis technique of a kind of 5 '-cytidine monophosphate according to claim 1, it is characterised in that in the step a
A small amount of PEG400 need to be added as phase transfer catalyst.
A kind of 8. Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate according to claim 1 or 7, it is characterised in that the born of the same parents
Pyrimidine, D-ribose, PEG400, sodium dihydrogen phosphate and pure water dosage in parts by weight：111.10 parts of cytimidine, D-ribose
600 parts of 150.13 parts, 0.11 part of PEG400,240 parts of sodium dihydrogen phosphate and pure water.
A kind of 9. Enzyme catalyzed synthesis technique of 5 '-cytidine monophosphate according to claim 1, it is characterised in that the synzyme I
Including cytidine ligase and NAD+, the content of the NAD+ is the 0.01%-0.02% of the cytidine ligase content, the synthesis
Enzyme II includes cytidine kinases and ATP, and the content of the ATP is the 0.1%-0.5% of the cytidine kinases content.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111269870A (en) * | 2020-03-06 | 2020-06-12 | 南京工业大学 | Recombinant escherichia coli with high cytidylic acid yield and application thereof |
| CN114292890A (en) * | 2022-01-12 | 2022-04-08 | 深圳华酶生物科技有限公司 | Novel method for synthesizing 5' -cytidylic acid by enzyme method |
-
2017
- 2017-07-26 CN CN201710615002.5A patent/CN107365812A/en active Pending
Non-Patent Citations (3)
| Title |
|---|
| TAKUZO NISHIMURA，ET AL: ".A new syn thetic method for pyrimidine and purine ribosides", 《CHEM PHARM BULL》 * |
| 方海田等: "微生物发酵法生产胞嘧啶核苷的研究进展", 《发酵科技通讯》 * |
| 李永等: "胞苷的合成", 《精细化工》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111269870A (en) * | 2020-03-06 | 2020-06-12 | 南京工业大学 | Recombinant escherichia coli with high cytidylic acid yield and application thereof |
| CN114292890A (en) * | 2022-01-12 | 2022-04-08 | 深圳华酶生物科技有限公司 | Novel method for synthesizing 5' -cytidylic acid by enzyme method |
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Application publication date: 20171121 |