CN100532386C - Production process of N- acetyl-D-amino mannose - Google Patents
Production process of N- acetyl-D-amino mannose Download PDFInfo
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- CN100532386C CN100532386C CNB2006101547054A CN200610154705A CN100532386C CN 100532386 C CN100532386 C CN 100532386C CN B2006101547054 A CNB2006101547054 A CN B2006101547054A CN 200610154705 A CN200610154705 A CN 200610154705A CN 100532386 C CN100532386 C CN 100532386C
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- isomerization reaction
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Abstract
The invention discloses a manufacturing method of N-acetyl-D-aminomannose, which comprises the following steps: adopting N-acetyl-D-aminoglucose as main raw material; dissolving in the water, dimethyl formamide or pyridine; adopting molybdic acid, ammonium molybdate, sodium molybdate or molybdenum complex compound as raw material to do isomerization reaction; making reacting system pass anion exchange resin column or cation exchange resin column; adding microbe or solidified microbe to decompose or adsorb N-acetyl-D-aminomannose and by-product; decoloring through activated charcoal; condensing in the vacuum or freezing in the vacuum; drying; condensing; crystallizing to obtain the pure product.
Description
Technical field
The present invention relates to a kind of production method of N-kharophen seminose.
Background technology
N-kharophen seminose is one of a few natural aminosugar, participate in constituting many agglutinin receptors, but the multiple glycan molecule on this receptor recognizing cells surface or the pathogen cells wall, by participating in receptor mediated endocytosis and phagolysis, environment is stable in keeping, and innate immunity and acquired immunity connected, form a kind of immune defense system of body.N-kharophen seminose can promote the growth and the breeding of zooblast, one of formation of Chang Zuowei Methods of Serum-Free Medium for Animal Cells simultaneously.N-kharophen seminose still is the main raw material of sialic acid synthetase, and the latter is synthetic multiple novel antiviral pharmaceutical intermediate.It is heterogeneous catalyst that N-kharophen seminose conventional production methods is to use alkali, and yield is low, separation and purification is difficult; And abroad some patents adopt microbial transformation or enzyme isomerization, as Japanese Patent JP2001078794, JP10182685, still exist microorganism that the katabolism of raw material is caused separation and purification difficulty and material loss; Other has patent is raw material with the sialic acid and produces N-kharophen seminose, although have advantage such as quick, environmental protection, sialic acid is difficult to obtain, and market value is also more expensive more than 2 times than N-kharophen seminose.
Summary of the invention
The objective of the invention is to overcome the deficiency of prior art, a kind of production method of new N-acetyl-D-amino mannose is provided, it can significantly reduce production costs, and improves product purity.
The present invention solves the problems of the technologies described above the technical scheme of being taked:
A kind of production method of N-acetyl-D-amino mannose is characterized in that comprising the steps:
With N-acetyl-D-amino glucose is main raw material, in the organic phases such as mixture of one or more in it is water-soluble, dimethyl formamide, the pyridine, the mass concentration of dimethyl formamide, pyridine or its mixture is 0～30%, with molybdic acid or ammonium molybdate or Sodium orthomolybdate or other molybdate, or molybdenum complex is catalyzer, and its concentration is 1mmol/L～1mol/L, the pH value is 6～14, temperature of reaction is 0～100 ℃, and the reaction times is 0.5～24hr, carries out isomerization reaction; After reaction finishes, after reaction system is passed through anion-exchange resin column and cation exchange resin column successively, adding can optionally be decomposed or the microorganism or the immobilized microorganism of absorption of N-acetyl-D-amino glucose and other by products, described microorganism is a bacterium, actinomycetes or mould or yeast, or or immobilization actinomycetes or immobilized yeast or immobilization mould, preferred yeast bacterium or mould, or the immobilization product of yeast, mould; Again through decolorizing with activated carbon, vacuum concentration or vacuum lyophilization concentrate crystallization, obtain pure product N-acetyl-D-amino mannose.
The present invention solves the problems of the technologies described above the further technical scheme of being taked:
Described isomerization reaction is preferably carried out at aqueous phase.
Described isomerization reaction is a catalyzer with ammonium molybdate or Sodium orthomolybdate, and its concentration is 0.05～1.5mol/L.
The pH value of described isomerization reaction is 10～13.
The temperature of described isomerization reaction is 20～50 ℃.
The described isomerization reaction time is 3～6hr.
Described anionite-exchange resin is D301, and 201 * 7 resins or D113, D201 * 7 resins, preferred 201 * 7 resins, described Zeo-karb are 001 * 7 resin or D001 * 7 resins, preferred 001 * 7 resin.
Because the present invention has adopted novel littleization agent to improve the isomery transformation efficiency, and adopt food microorganisms and immobilized microorganism selectivity to absorb impurity in the decomposition reaction system, significantly reduced production cost, improved product purity (reaching more than 99%).
Embodiment
With embodiment the present invention is described in further detail below.
Embodiment 1
N-acetyl-D-amino glucose 100g adds water 3L dissolving back and adds molybdic acid 30mmol, transfer pH13 with NaOH, be warmed up to 60 ℃, insulation 3hr postcooling is successively by behind D301 resin and 001 * 7 resin, add candiyeast 50g fermentation 24hr, remove by filter thalline, add the removal of impurities of 30g decolorizing with activated carbon and filter, filtrate is concentrated to crystal and separates out, crystallisation by cooling, the dry finished product 62g that gets.
Embodiment 2
N-acetyl-D-amino glucose 100g adds dimethyl formamide (DMF) 2L dissolving, adds the molybdenum network 100mmol of 2-4-diacetylmethane, transfers pH13 with NaOH, be warmed up to 80 ℃, insulation 5hr postcooling successively by behind D201 * 7 resins and D001 * 7 resins, adds immobilization rhizopus 100g behind the adding distil water 2L, fermentation 36hr, the filtering thalline adds the removal of impurities of 30g decolorizing with activated carbon and filters, and filtrate is concentrated in vacuo to crystal and separates out, crystallisation by cooling, filtering drying get finished product 26g.
Embodiment 3
N-acetyl-D-amino glucose 100g adds water 5L, add pyridine 2L, add 1mol ammonium molybdate stirring and dissolving, transfer pH9.5 with ammoniacal liquor, pass through D201 * 7 resins and D001 * 7 resins successively after stirring 24hr under the room temperature, add immobilized yeast 80g fermentation 36hr, the filtering thalline, decolouring, the lyophilize crystallization gets finished product 35g.
Embodiment 4
N-acetyl-D-amino glucose 10kg adds water 50L, add 3.5mol potassium molybdate stirring and dissolving, transfer pH13 with 40%NaOH, pass through D201 * 7 resins and D113 resin column successively after stirring 24hr under the room temperature, be warmed up to 40 ℃, the 10L fixed yeast bacterial spawn 36hr that flows through again, decolouring, the lyophilize crystallization gets finished product 5.7kg.
Embodiment 5
N-acetyl-D-amino glucose 50kg adds water 500L, add 25mol Sodium orthomolybdate stirring and dissolving, transfer pH12 with 40%KOH, 45 ℃ are passed through 201 * 7 resins and 001 * 7 resin column behind the stirring 5hr down successively, adjust temperature to 40 ℃, the 120L immobilization of flowing through again head mold bacterial spawn 20hr, decolouring, vacuum concentration, crystallization get finished product 33kg.
Embodiment 6
N-acetyl-D-amino glucose 100kg adds water 1500L, add 65mol aluminic acid stirring and dissolving, transfer pH14 with 40%KOH, 50 ℃ are passed through 201 * 7 resins and 001 * 7 resin column behind the stirring 6hr down successively, adjust temperature to 35 ℃, the 260L fixed yeast bacterial spawn 45hr that flows through again, decolouring, the lyophilize crystallization gets finished product 65kg.
Claims (8)
1, a kind of production method of N-acetyl-D-amino mannose is characterized in that comprising the steps:
With N-acetyl-D-amino glucose is main raw material, in the mixture of one or more in it is water-soluble, dimethyl formamide, the pyridine, the mass concentration of dimethyl formamide, pyridine or its mixture is 0～30%, with molybdic acid or ammonium molybdate or Sodium orthomolybdate or other molybdate, or molybdenum complex is catalyzer, and its concentration is 1mmol/L～1mol/L, the pH value is 6～14, temperature of reaction is 0～100 ℃, and the reaction times is 0.5～24hr, carries out isomerization reaction; After reaction finishes, after reaction system is passed through anion-exchange resin column and cation exchange resin column successively, adding can optionally be decomposed or the microorganism or the immobilized microorganism of absorption of N-acetyl-D-amino glucose and other by products, described microorganism or fixation of microbe are actinomycetes or mould or yeast, or immobilization actinomycetes or immobilized yeast or immobilization mould; Again through decolorizing with activated carbon, vacuum concentration or vacuum lyophilization concentrate crystallization, obtain pure product N-acetyl-D-amino mannose.
2, the production method of N-acetyl-D-amino mannose according to claim 1 is characterized in that: described isomerization reaction is carried out at aqueous phase.
3, the production method of N-acetyl-D-amino mannose according to claim 1 is characterized in that: described isomerization reaction is a catalyzer with ammonium molybdate or Sodium orthomolybdate, and its concentration is 0.05～1.5mol/L.
4, the production method of N-acetyl-D-amino mannose according to claim 1 is characterized in that: the pH value of described isomerization reaction is 10～13.
5, the production method of N-acetyl-D-amino mannose according to claim 1 is characterized in that: the temperature of described isomerization reaction is 20～50 ℃.
6, the production method of N-acetyl-D-amino mannose according to claim 1 is characterized in that: the described isomerization reaction time is 3～6hr.
7, the production method of N-acetyl-D-amino mannose according to claim 1, it is characterized in that: described anionite-exchange resin is D301,201 * 7 resins or D113, D201 * 7 resins, described Zeo-karb are 001 * 7 resin or D001 * 7 resins.
8, the production method of N-acetyl-D-amino mannose according to claim 7 is characterized in that: described anionite-exchange resin is 201 * 7 resins, and described Zeo-karb is 001 * 7 resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101547054A CN100532386C (en) | 2006-11-15 | 2006-11-15 | Production process of N- acetyl-D-amino mannose |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101547054A CN100532386C (en) | 2006-11-15 | 2006-11-15 | Production process of N- acetyl-D-amino mannose |
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| Publication Number | Publication Date |
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| CN1962676A CN1962676A (en) | 2007-05-16 |
| CN100532386C true CN100532386C (en) | 2009-08-26 |
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| CNB2006101547054A Expired - Fee Related CN100532386C (en) | 2006-11-15 | 2006-11-15 | Production process of N- acetyl-D-amino mannose |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113214328B (en) * | 2021-05-08 | 2022-06-28 | 宁波经济技术开发区弘翔生化科技有限公司 | Double-aqueous-phase system and monosaccharide separation method based on double-aqueous-phase system |
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2006
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Non-Patent Citations (2)
| Title |
|---|
| 葡萄糖催化制取甘露糖的正交试验分析. 赵光辉等.当代化工，第34卷第1期. 2005 |
| 葡萄糖催化制取甘露糖的正交试验分析. 赵光辉等.当代化工，第34卷第1期. 2005 * |
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| CN1962676A (en) | 2007-05-16 |
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Granted publication date: 20090826 Termination date: 20121115 |