CN106834378A - A kind of method that utilization mannose prepares the phosphoric acid of mannose 6 - Google Patents
A kind of method that utilization mannose prepares the phosphoric acid of mannose 6 Download PDFInfo
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Abstract
The present invention relates to a kind of method that utilization mannose prepares the phosphoric acid of mannose 6.Comprise the following steps：(1) preparation of D mannoses；(2) reaction solution is prepared, D mannoses, adenosine triphosphate acid sodium-salt and/or calgon, MgCl2 dissolvings obtained in step (1) in deionized water, pH value is adjusted into Tris Hcl buffer solutions；Wherein D mannose concentrations are 300 800mmol/L, and adenosine triphosphate acid sodium-salt and/or hexa metaphosphoric acid na concn are 500 1500mmol/L, and MgCl2 concentration is 10 100mmol/L, and pH value is 49；(3) hexokinase mixing is added, the bed reaction that shakes of 15 50 DEG C of reaction temperature is then placed on, 100rpm concussion incubations is allowed to carry out conversion reaction 5 48 hours；(4) activated carbon decolorizing, filtering are added；(5) KOH is added, then separating-purifying is carried out using SSMB, is concentrated, be drying to obtain.By the way that to D mannose preparation technology parameters, enzymatic reaction synthesizes the optimization of the phosphoric acid process parameter of mannose 6 so that raw material selection is simpler, and combined coefficient is higher, and the purity of the phosphoric acid of mannose 6 reaches more than 99%.
Description
Technical field
The invention belongs to biological chemical field, the method that more particularly to a kind of enzyme process prepares Man-6-P.
Background technology
Man-6-P（English：Mannose-6-phosphate, M6P）Be one in immune system with agglutinin
With reference to molecule, M6P can be converted into fructose-6-phosphate by phosphomannose isomerase.During protein metabolism, with cell
Endosome, the cell membrane protein relevant with cell exocrine thing have to pass through the most final position in modification ability transporte to cells
Put.6- phosphomannoses (mannose-6-phosphate, M-6-P) are exactly to be widely present in being repaiied with protein in life entity
The closely related phosphorylated carbohydrate compound of decorations.Its corresponding acceptor 6- phosphomamloses saccharide acceptor (mannose-6- of M-6-P
Phosphate receptor, M-6-P receptor) combine, important work is played during lysosomal enzyme generating effect
With M-6-P is the sorter and delivery person of lysosomal enzyme.
Refer to Man-6-P in the patent No. 201080035798.3 and its salt, its precursor or its analog have and subtract
The purposes of few rubefaction, while having cosmetic result, and can accelerate the healing of damaged skin.In recent years, it is with M-6-P
The drug research of precursor is of increasing concern, and demand of the people for M-6-P is also lifted therewith.Therefore, find a kind of extensive
The method for producing M-6-P is necessary.
At present, most of people synthesize the analog of M-6-P using chemical method, and it is non-to synthesize M-6-P using enzyme process
Normal lacks.Chemical method is substantially with methyl α-D- mannopyranoses glycosides or the-O-b benzyl-α-D- pyrroles of methyl 2,3,4- tri-
Mannoside of muttering is the synthesis step that starting material is walked by 3-5, and formation has the analog of similar structure to M-6-P.Synthesized
Condition required for journey is harsher, it is necessary to low temperature environment or need the participation of heavy metal or toxic reagent, and always reclaims
Rate is not also high.
For analog compared to chemical method synthesis M-6-P, enzymatic clarification M-6-P has high catalytic efficiency, reaction bar
The gentle advantage of part, and without the participation of organic reagent and heavy metal, advantageously in the pharmaceutical synthesis in later stage.
The invention provides a kind of method that utilization mannose prepares Man-6-P.
The content of the invention
It is an object of the invention to provide a kind of method that mannose prepares Man-6-P, by D-MANNOSE
Preparation technology parameter, enzymatic reaction synthesizes the optimization of Man-6-P technological parameter so that raw material selects simpler, work
Skill flow understands detailed, combined coefficient more preferably, while the purity of the Man-6-P for preparing is higher, reach 99% with
On.
Technical scheme is as follows：
A kind of method that utilization mannose prepares Man-6-P, comprises the following steps：
(1) preparation of D-MANNOSE：A. by mol ratio (1-10)：(1-2) glucose and fructose purified water are diluted to concentration 25-
65% (quality), adds catalyst molybdate, and the molybdate is 0.1-1 with the ratio of glucose and fructose quality sum：50,
Epimerism is carried out under 50-110 DEG C of vacuum condition, the isomery mixed liquor for obtaining；B. glucose, the fruit for step a being obtained
Sugar, the mixed liquor of mannose, separating-purifying is carried out after carrying out desalting refinement into Simulation moving bed, obtains the group rich in mannose
Divide A and other components B；Other components B is returned into step a carries out epimerism；C by step b obtain rich in mannose
Component A, carries out flush distillation and is subsequently adding activated carbon being decolourized, through desolventing technology after, carry out double evaporation-cooling, obtain feed liquid,
The feed liquid carries out aqueous crystallization, the falling temperature gradient control in crystallization process：0~6 hour, 0.5-1 DEG C was dropped per hour；7~18 is small
When, 1-2 DEG C is dropped per hour；After 19 hours, 0.5-1 DEG C is dropped per hour, until 20~30 DEG C are down to, through centrifugation essence after crystallization
System, obtains crude crystalline D-MANNOSE, and immersion in 15-60 minutes is carried out to thick D-MANNOSE with the absolute ethyl alcohol of 20-40% refines,
D-MANNOSE finished product is obtained after drying;
(2) prepare reaction solution, by D-MANNOSE, adenosine triphosphate acid sodium-salt and/or calgon obtained in step (1),
MgCl2Dissolving in deionized water, pH value is adjusted with Tris-Hcl buffer solutions；Wherein D-MANNOSE concentration is 300-800mmol/
L, adenosine triphosphate acid sodium-salt and/or hexa metaphosphoric acid na concn are 500-1500mmol/L, MgCl2Concentration is 10-100mmol/L,
PH value is 4-9；
(3) hexokinase mixing is added, the bed reaction that shakes of 15-50 DEG C of reaction temperature, 100rpm concussion temperature is then placed on
Educate and be allowed to carry out conversion reaction 5-48 hours；
(4) activated carbon decolorizing, filtering are added；
(5) KOH is added, then separating-purifying is carried out using SSMB, is concentrated, be drying to obtain.
Preferably, in step (1), the mol ratio (9-10) of glucose and fructose：(1-1.2), is diluted to dense with purified water
38% (quality) of degree, the molybdate is 0.8-1 with the ratio of glucose and fructose quality sum：50.
Preferably, in step (2), D-MANNOSE concentration is 500-800mmol/L, adenosine triphosphate acid sodium-salt and/or six inclined
Phosphoric acid na concn is 500-1200mmol/L, and-mannose is 1 with adenosine triphosphate acid sodium-salt and/or calgon mol ratio：
2.3。
Preferably, in step (2), MgCl2Concentration is the 1/3-1/9 of D-MANNOSE concentration.
Preferably, in step (2), pH value is 6.5-8.8.
Preferably, adenosine triphosphate acid sodium-salt and calgon mol ratio are 1-10：10-1.
The invention has the advantages that：
(1) present invention uses enzymatic clarification M-6-P, for the analog compared to chemical method synthesis M-6-P, enzymatic clarification M-6-
P have the advantages that high catalytic efficiency, reaction condition it is gentle, efficiently, green safety, and only need to obtain hexokinase from market
As raw material, beneficial to industrialized production；
(2) present invention is by the way that to D-MANNOSE preparation technology parameter, enzymatic reaction synthesizes the excellent of Man-6-P technological parameter
Change so that raw material selection is simpler, technological process understands detailed, and combined coefficient is more preferable, while the mannose -6- for preparing
The purity of phosphoric acid is higher, reaches more than 99%.
Other features and advantages of the present invention will illustrate in the following description, and partly become from specification
It is clear that or being understood by implementing the present invention.The main object of the present invention and further advantage can be by specification, power
Specifically noted scheme is realized and obtained in sharp claim.
Brief description of the drawings
Accompanying drawing is only used for showing the purpose of specific embodiment, and is not considered as limitation of the present invention, in whole accompanying drawing
In, identical reference symbol represents identical part.
Fig. 1 is the process chart that Man-6-P is prepared using mannose.
Specific embodiment
Embodiment 1
A kind of method that utilization mannose prepares Man-6-P, it is characterised in that comprise the following steps：
(1) preparation of D-MANNOSE：A. by mol ratio 8：1 glucose and fructose purified water are diluted to concentration 40% (quality),
Catalyst molybdate is added, the molybdate is 0.2 with the ratio of glucose and fructose quality sum：50, in 65 DEG C of vacuum
Under the conditions of carry out epimerism, the isomery mixed liquor for obtaining；B. glucose, fructose, the mixing of mannose for step a being obtained
Liquid, separating-purifying is carried out after carrying out desalting refinement into Simulation moving bed, obtains component A and other components B rich in mannose；
Other components B is returned into step a carries out epimerism；The component A rich in mannose that c obtains step b, is once steamed
Hair is subsequently adding activated carbon and is decolourized, through desolventing technology after, carry out double evaporation-cooling, obtain feed liquid, the feed liquid is entered water-filling and is mutually tied
Crystalline substance, the falling temperature gradient control in crystallization process：0~6 hour, 0.5 DEG C was dropped per hour；7~18 hours, 1.5 DEG C were dropped per hour；19
After hour, 0.5 DEG C is dropped per hour, until being down to 26 DEG C, through centrifuge refining after crystallization, obtain crude crystalline D-MANNOSE, with
35% absolute ethyl alcohol carries out immersion in 40 minutes to thick D-MANNOSE and refines, and D-MANNOSE finished product is obtained after drying；
(2) reaction solution is prepared, by D-MANNOSE, adenosine triphosphate acid sodium-salt, MgCl obtained in step (1)2It is dissolved in deionization
In water, pH value is adjusted with Tris-Hcl buffer solutions；Wherein D-MANNOSE concentration be 500mmol/L, adenosine triphosphate acid sodium-salt and/or
Hexa metaphosphoric acid na concn is 1300mmol/L, MgCl2Concentration is 12mmol/L, and pH value is 6；
(3) hexokinase is added（Commercially available, sigma companies produce CAS：9001-51-8）Mixing, is then placed on reaction
30 DEG C of temperature shakes bed reaction, and 100rpm concussion incubations are allowed to carry out conversion reaction 36 hours；
(4) activated carbon decolorizing, filtering are added；
(5) KOH is added, then separating-purifying is carried out using SSMB, is concentrated, be drying to obtain.
Conversion ratio reaches more than 90%, and the purity of the Man-6-P after purification reaches 99.2%.
Embodiment 2
A kind of method that utilization mannose prepares Man-6-P, comprises the following steps：
(1) preparation of D-MANNOSE：A. by mol ratio 8：1 glucose and fructose purified water are diluted to concentration 30% (quality),
Catalyst molybdate is added, the molybdate is 1 with the ratio of glucose and fructose quality sum：50, in 80 DEG C of vacuum bar
Epimerism is carried out under part, the isomery mixed liquor for obtaining；B. glucose, fructose, the mixed liquor of mannose for step a being obtained,
Separating-purifying is carried out into Simulation moving bed after carrying out desalting refinement, component A and other components B rich in mannose is obtained；Will
Other components B returns to step a and carries out epimerism；The component A rich in mannose that c obtains step b, carries out flush distillation
Activated carbon is subsequently adding to be decolourized, through desolventing technology after, carry out double evaporation-cooling, obtain feed liquid, the feed liquid carries out aqueous crystallization,
Falling temperature gradient control in crystallization process：0~6 hour, 1 DEG C was dropped per hour；7~18 hours, 2 DEG C were dropped per hour；19 hours with
Afterwards, 1 DEG C is dropped per hour, until being down to 22 DEG C, through centrifuge refining after crystallization, crude crystalline D-MANNOSE is obtained, with 25% nothing
Water-ethanol carries out immersion in 50 minutes to thick D-MANNOSE and refines, and D-MANNOSE finished product is obtained after drying；
(2) reaction solution is prepared, by D-MANNOSE, calgon, MgCl2 dissolvings obtained in step (1) in deionized water,
PH value is adjusted with Tris-Hcl buffer solutions；Wherein D-MANNOSE concentration is 350mmol/L, adenosine triphosphate acid sodium-salt and/or six inclined
Phosphoric acid na concn is 780mmol/L, and MgCl2 concentration is 40mmol/L, and pH value is 8.5；
(3) hexokinase is added（It is commercially available, brand：Star section is biological）Mixing, is then placed on shaking for 40 DEG C of reaction temperature
Bed reaction, 100rpm concussion incubations are allowed to carry out conversion reaction 20 hours；
(4) activated carbon decolorizing, filtering are added；
(5) KOH is added, then separating-purifying is carried out using SSMB, is concentrated, be drying to obtain.
Conversion ratio reaches more than 90%, and the purity of the Man-6-P after purification reaches 99.35%.
Embodiment 3
A kind of method that utilization mannose prepares Man-6-P, comprises the following steps：
(1) preparation of D-MANNOSE：A. by mol ratio 2：1 glucose and fructose purified water are diluted to concentration 33% (quality),
Catalyst molybdate is added, the molybdate is 0.2 with the ratio of glucose and fructose quality sum：50, in 55 DEG C of vacuum
Under the conditions of carry out epimerism, isomery glucose, fructose, the mannose mixed liquor for obtaining；Glucose that b. step a is obtained,
The mixed liquor of fructose, mannose, separating-purifying is carried out after carrying out desalting refinement into Simulation moving bed, is obtained rich in mannose
Component A and other components B；Other components B is returned into step a carries out epimerism；C by step b obtain rich in mannose
Component A, carry out flush distillation and be subsequently adding activated carbon being decolourized, through desolventing technology after, carry out double evaporation-cooling, expected
Liquid, the feed liquid carries out aqueous crystallization, the falling temperature gradient control in crystallization process：0~6 hour, 0.8 DEG C was dropped per hour；7~18 is small
When, 1.2 DEG C are dropped per hour；After 19 hours, 1 DEG C is dropped per hour, until being down to 25 DEG C, through centrifuge refining after crystallization, obtain thick
Product crystallize D-MANNOSE, and immersion in 55 minutes is carried out to thick D-MANNOSE with 28% absolute ethyl alcohol refines, and it is sweet to obtain D- after drying
The sugared finished product of dew；
(2) reaction solution is prepared, by D-MANNOSE, adenosine triphosphate acid sodium-salt and calgon, MgCl obtained in step (1)2
Dissolving in deionized water, pH value is adjusted with Tris-Hcl buffer solutions；Wherein D-MANNOSE concentration is 400mmol/L, adenosine three
Sodium ascorbyl phosphate concentration is 400mmol/L, and hexa metaphosphoric acid na concn is 250mmol/L, MgCl2Concentration is 25mmol/L, and pH value is
7.5；
(3) hexokinase is added（It is commercially available, brand：Star section is biological）Mixing, is then placed on shaking for 30 DEG C of reaction temperature
Bed reaction, 100rpm concussion incubations are allowed to carry out conversion reaction 35 hours；
(4) activated carbon decolorizing, filtering are added；
(5) KOH is added, then separating-purifying is carried out using SSMB, is concentrated, be drying to obtain.
Conversion ratio reaches more than 90%, and the purity of the Man-6-P after purification reaches 99.5%.
The above only present invention preferably specific embodiment, but protection scope of the present invention is not limited thereto, and appoints
What those familiar with the art the invention discloses technical scope in the change or replacement expected, should all cover
Within protection scope of the present invention.
Claims (6)
1. a kind of method that utilization mannose prepares Man-6-P, it is characterised in that comprise the following steps：
(1) preparation of D-MANNOSE：
A. by mol ratio (1-10)：(1-2) glucose and fructose purified water are diluted to concentration 25-65% (quality), and addition is urged
Agent molybdate, the molybdate is 0.1-1 with the ratio of glucose and fructose quality sum：50, in 50-110 DEG C of vacuum
Under the conditions of carry out epimerism, isomery glucose, fructose, the mannose mixed liquor for obtaining；
B. glucose, fructose, the mixed liquor of mannose for step a being obtained, enter after carrying out desalting refinement into Simulation moving bed
Row separating-purifying, obtains component A and other components B rich in mannose；Other components B is returned into step a to be differed to different
Structure；
The component A rich in mannose that c obtains step b, carries out flush distillation and is subsequently adding activated carbon being decolourized, through decolourizing
After treatment, double evaporation-cooling is carried out, obtain feed liquid, the feed liquid carries out aqueous crystallization, the falling temperature gradient control in crystallization process：0~6
Hour, 0.5-1 DEG C is dropped per hour；7~18 hours, 1-2 DEG C was dropped per hour；After 19 hours, 0.5-1 DEG C is dropped per hour, until
20~30 DEG C are down to, through centrifuge refining after crystallization, crude crystalline D-MANNOSE are obtained, with the absolute ethyl alcohol of 20-40% to thick D-
Mannose carries out immersion in 15-60 minutes and refines, and D-MANNOSE finished product is obtained after drying；
(2) reaction solution is prepared, by D-MANNOSE, adenosine triphosphate acid sodium-salt and/or calgon, MgCl obtained in step (1)2
Dissolving in deionized water, pH value is adjusted with Tris-Hcl buffer solutions；Wherein D-MANNOSE concentration is 300-800mmol/L, gland
Guanosine triphosphate sodium salt and/or hexa metaphosphoric acid na concn are 500-1500mmol/L, MgCl2Concentration is 10-100mmol/L, pH value
It is 4-9；
(3) hexokinase mixing is added, the bed reaction that shakes of 15-50 DEG C of reaction temperature, 100rpm concussion temperature is then placed on
Educate and be allowed to carry out conversion reaction 5-48 hours；
(4) activated carbon decolorizing, filtering are added；
(5) KOH is added, then separating-purifying is carried out using SSMB, is concentrated, be drying to obtain.
2. the method for preparing Man-6-P using mannose as claimed in claim 1, it is characterised in that step (1)
In, the mol ratio (9-10) of glucose and fructose：(1-1.2), concentration 38% (quality), the molybdate are diluted to purified water
It is 0.8-1 with the ratio of glucose and fructose quality sum：50.
3. the method for preparing Man-6-P using mannose as claimed in claim 1 or 2, it is characterised in that step
(2) in, D-MANNOSE concentration is 500-800mmol/L, and adenosine triphosphate acid sodium-salt and/or hexa metaphosphoric acid na concn are 500-
1200mmol/L, D-MANNOSE is 1 with adenosine triphosphate acid sodium-salt and/or calgon mol ratio：2.3.
4. the method that the utilization mannose as described in one of claim 1-3 prepares Man-6-P, it is characterised in that step
Suddenly in (2), MgCl2Concentration is the 1/3-1/9 of D-MANNOSE concentration.
5. the method that the utilization mannose as described in one of claim 1-4 prepares Man-6-P, it is characterised in that step
Suddenly in (2), pH value is 6.5-8.8.
6. the method that the utilization mannose as described in one of claim 1-5 prepares Man-6-P, it is characterised in that gland
Guanosine triphosphate sodium salt is 1-10 with calgon mol ratio：10-1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114686541A (en) * | 2022-02-28 | 2022-07-01 | 北京焉支山科技有限公司 | Biological enzyme synthesis method and application of cosmetic-grade hexose-6-phosphate composition |
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| CN101851689A (en) * | 2010-06-11 | 2010-10-06 | 谭卫星 | Preparation process of D-mannose |
| CN104673855A (en) * | 2015-03-27 | 2015-06-03 | 北京化工大学 | Method for synthesizing 6-hexose phosphate by employing enzymic method |
| CN105001273A (en) * | 2015-07-07 | 2015-10-28 | 白心亮 | Preparation method for mannose |
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2017
- 2017-02-16 CN CN201710083757.5A patent/CN106834378A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101851689A (en) * | 2010-06-11 | 2010-10-06 | 谭卫星 | Preparation process of D-mannose |
| CN104673855A (en) * | 2015-03-27 | 2015-06-03 | 北京化工大学 | Method for synthesizing 6-hexose phosphate by employing enzymic method |
| CN105001273A (en) * | 2015-07-07 | 2015-10-28 | 白心亮 | Preparation method for mannose |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114686541A (en) * | 2022-02-28 | 2022-07-01 | 北京焉支山科技有限公司 | Biological enzyme synthesis method and application of cosmetic-grade hexose-6-phosphate composition |
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