CN105734096A - Method for preparing mannose through biological process - Google Patents
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- CN105734096A CN105734096A CN201410748870.7A CN201410748870A CN105734096A CN 105734096 A CN105734096 A CN 105734096A CN 201410748870 A CN201410748870 A CN 201410748870A CN 105734096 A CN105734096 A CN 105734096A
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Abstract
The invention discloses a method for preparing mannose through a biological process. According to the method, one or two of sodium formate and calcium formate, and one or two of glucose and fructose are taken as the raw materials, under the condition that glucose isomerase is available or not available, a biological catalysis system composed of an NAD (P)H-dependent mannitol dehydrogenase, an NAD(P)<+>-dependent formate dehydrogenase, an NAD<+>-dependent mannitol dehydrogenase, an NADH oxidase and a coenzyme is adopted for catalyzing, so that the mannose is prepared. The method for preparing the mannose provided by the invention has the characteristics that the raw materials are cheap, the reaction selectivity is high, etc, and the method belongs to a novel preparation reaction route of the mannose.
Description
Technical field
The invention belongs to biological technical field, specifically, be the production method about a kind of mannose.
Background technology
Mannose, be the difference of a kind of glucose to isomers, have regulate immunity, the effect of the aspect such as the normal synthesis infecting, promoting internal glycoprotein of resisting antibacterial and virus.In recent years, mannose is used widely at functional food, feed additive and field of medicaments, is developed a series of products such as glycoprotein syndrome medicine of mannose functional food, mannose feed additive, urethritis and cystitis treatments medicine, sugar defect.
Mannose can separate preparation from some lignocellulose containing mannose component or glucomannan hydrolyzed solution.nullSuch as,Ge Mingjuan et al. has invented a kind of technique preparing mannose for raw material by biological degradation method with Rhizoma amorphophalli,But process route is loaded down with trivial details and mannose yield is only at about 15% (Chen,Y.,etal.,BiologicalpreparationofD-mannose,involveshydrolyzingkonjacflour,addingyeast,fermenting,decolorizingandremovingyeast,concentratingsolution,mixingwithseedcrystalofsolvent,denitrifyingandcentrifugingproduct.2011.);Chinese Academy of Sciences Fang Zhen et al. has carried out microwave-assisted dilute acid hydrolysis method and has carried out the research of mannose production preparation from palm fruit residue, the productivity of mannose can reach 92.11%, but the method exists to be needed to use substantial amounts of acid and organic solvent (Fan, S.-P., etal., Highyieldproductionofsugarsfromdeproteinatedpalmkernelca keundermicrowaveirradiationviadilutesulfuricacidhydrolys is.BioresourceTechnology, 2014.153 (0): p.69-78.);Saari et al. adopts ion-exchange-resin process to carry out the separation and Extraction of mannose from the dilute acid hydrolysis liquid of lignin, but the ratio shared in material composition due to mannose is relatively low, cause the problem (Saari that the separating-purifying cost of mannose is high, P.andM.Hurme, ProcessSynthesisPrinciplesintheChromatographicSeparation ofSugarsfromBiomassHydrolysates.ChemicalEngineering&Tech nology, 2011.34 (2): p.282-288).At present, because because material composition is complicated, the mannose production technology route ubiquity of the type causes that separation purifying technique cost is high, reaction process uses substantial amounts of diluted acid and organic solvent easily cause the problems such as environmental pollution, and cause prepared by the large-scale production that this technology path is not appropriate for mannose.
Mannose can also be prepared from glucose or fructose through isomerate process.Kockritz et al. develops the catalyst of a kind of molybdate-carried ion exchange resin, there is the activity that catalysis glucose isomerase is mannose, the yield of mannose reaches as high as 28% (Kockritz, A., etal., Rearrangementofglucosetomannosecatalysedbypolymer-suppor tedMocatalystsintheliquidphase.AppliedCatalysisa-General, 2008.334 (1-2): p.112-118.).Gunther et al. adopts Sn-Beta molecular sieve catalyst and boric acid to carry out the research of glucose isomerization mannose, the yield of mannose is up to 15%% (Gunther, W.R., etal., Sn-Betazeoliteswithboratesaltscatalysetheepimerizationof carbohydratesviaanintramolecularcarbonshift.NatCommun, 2012.3:p.1109.).Mannose is except can passing through chemical isomerization method and being prepared by glucose or fructose, it is possible to prepared through enzyme isomerate process by mannose isomerase, lyxose isomerase, cellobiose isomerase etc..Such as, Park et al. adopts lyxose isomery enzyme process to carry out catalysis fructose and produces the research of mannose, the yield of mannose is up to 25% (Park, C.S., etal., MannoseproductionfromfructosebyfreeandimmobilizedD-lyxos eisomerasesfromProvidenciastuartii.BiotechnolLett, 2010.32 (9): p.1305-9).But, the reaction scheme that chemical isomerization or enzyme isomerate process produce mannose is adopted all to be subject to restriction thermodynamically, in reality, reaction conversion ratio is only about 30%, and reacting final product is generally the mixture of mannose, glucose and fructose, causes raw material availability low and the separating difficulty of mannose is big.
For the reaction being thermodynamically unfavorable for that target product synthesizes, by adopting the strategy of coupled reaction to change the thermodynamic equilibrium state of overall reaction system, it is so that the ongoing a kind of available strategy of some single reactions originally not easily carried out.In the substance metabolism and energy metabolic pathways of organism, also it is the strategy by have employed coupled reaction so that the biochemical reaction not easily carried out in chemical thermodynamics in a large number is carried out, thus ensure that the normal function of life.And in these coupled reactions, coenzyme plays important role.
In recent years, the biosynthesis research that chemicals is carried out in the biological coupling reaction that coenzyme participates in is utilized to receive significant attention.Nature has been found that a kind of mannitol-1-dehydrogenase (EC1.1.1.255), under pH neutrality and weak basic condition, mannitol can be converted into mannose, and NAD+ is converted into NADH (Stoop, J.M.H., etal., CharacterizationofNad-DependentMannitolDehydrogenasefrom CelerySuspension-Cultures.PlantPhysiology, 1995.108 (2): p.107-107.).But, not yet have with glucose or fructose for raw material, utilize the report of Cofactor Regeneration Systems catalytic production mannose.
Summary of the invention
It is an object of the invention to provide the production method of a kind of mannose.
The present invention is with the one in a kind of in sodium formate or calcium formate or two kinds and glucose or fructose or two kinds for raw material;By the living things catalysis system that oxidoreductase and coenzyme are constituted, or the living things catalysis system that glucose isomerase, oxidoreductase and coenzyme are constituted, catalytic production mannose;Oxidoreductase is the mannitol dehydrogenase of NAD (P) H dependence, NAD (P)+The hydrogenlyase of dependent form, NAD+One or two or more kinds in the mannitol dehydrogenase of dependence, nadh oxidase.
Concrete, when adopting glucose or glucose, fructose mixture, by the effect of glucose isomerase, convert glucose into fructose;Fructose, under the effect of NAD (P) the H mannitol dehydrogenase (EC1.1.1.138 or EC1.1.1.67) relied on and coenzyme NAD H or NADPH, generates mannitol and NAD (P)+, the NAD (P) of generation+At NAD (P)+Under the effect of the hydrogenlyase (EC1.2.1.43, EC1.2.1.2) of dependent form, generate NAD (P) H, and formates is changed into carbon dioxide;Mannitol is subsequently by NAD+The mannitol dehydrogenase (EC1.1.1.255) relied on and coenzyme NAD+Effect under, generate mannose and NADH, the NADH of generation under the effect of nadh oxidase, generate NAD+, it is achieved the regeneration of coenzyme.
The production method of mannose provided by the invention, described glucose isomerase, in aqueous systems, consumption is 0-100000U/L, zymetology classification number is EC5.3.1.5, is selected from: but it is not limited to the one in the glucose isomerase in the glucose isomerase in streptomyces source, the glucose isomerase in actinomyces source, bacillus source or two kinds.
The mannitol dehydrogenase that described NAD (P) H relies on is the NADH mannitol dehydrogenase relied on or the mannitol dehydrogenase of NADPH dependence, consumption 100U/L-1000000U/L in aqueous systems, zymetology classification number is EC1.1.1.138 and EC1.1.1.67, is selected from: but it is not limited to the one in the mannitol dehydrogenase in the mannitol dehydrogenase in Agaricus source, the mannitol dehydrogenase in mycocandida source, the mannitol dehydrogenase in Lactobacillus source, the mannitol dehydrogenase in Leuconostoc source, Rhodopseudomonas source or two kinds.
Described NAD (P)+The hydrogenlyase of dependent form is NAD+The hydrogenlyase of dependent form or NADP+The hydrogenlyase of dependent form, in aqueous systems, consumption is 100U/L-1000000U/L, zymetology classification number is EC1.2.1.43, EC1.2.1.2, is selected from: but it is not limited to the one in the hydrogenlyase in the hydrogenlyase in mycocandida source, the hydrogenlyase in Burkholderia source, the hydrogenlyase in Rhodopseudomonas source, the hydrogenlyase in bacillus source, fusobacterium source or two kinds.
Described NAD+The mannitol dehydrogenase relied on, in aqueous systems, consumption is 100U/L-1000000U/L, and zymetology classification number is EC1.1.1.255, is selected from: but it is not limited to the mannitol dehydrogenase in Herba Apii graveolentis source.
Described nadh oxidase, consumption 100U/L-1000000U/L in aqueous systems, zymetology classification number is EC1.6.3.4, is selected from: but it is not limited to the one in Streptococcus nadh oxidase, Lactobacillus nadh oxidase, fusobacterium nadh oxidase or two kinds.
Described coenzyme is NADH or NAD+In one or two kinds, and NADPH or NADP+In one or two kinds;NADH and NAD in system+Amount 5mM-500mM, NADPH and NADP in system+Amount 5mM-500mM.
In aqueous systems, the whole mass concentration of glucose or fructose is the whole mass concentration of 0.5-20%, sodium formate or calcium formate is 0.25%-2%, adopts formic acid regulation and control reaction pH=6-8, and reaction temperature is 10-60 degree.
Described living things catalysis system can have, for expression, mannitol dehydrogenase, the NAD (P) that glucose isomerase, NAD (P) H rely on+The hydrogenlyase of dependent form, NAD+The mannitol dehydrogenase that relies on, one or more cells of nadh oxidase, and utilize NADH, NAD in cell+, NADPH and NADP+, and cell own metabolism regeneration of NAD+For NADH or NADP+For the cell own metabolism regenerating coenzyme system of NADPH, the living things catalysis system of composition;Or, described living things catalysis system can be independent of the glucose isomerase of active somatic cell, the mannitol dehydrogenase of NAD (P) H dependence, NAD (P)+The hydrogenlyase of dependent form, NAD+Mannitol dehydrogenase, nadh oxidase and NADH, the NAD relied on+, NADPH and NADP+, the living things catalysis system of composition.
Specifically, described be raw material production mannose with glucose or fructose living things catalysis system have glucose isomerase (EC5.3.1.5), NAD (P) H to rely on for expression mannitol dehydrogenase (EC1.1.1.138 or EC1.1.1.67), NAD (P)+The hydrogenlyase (EC1.2.1.43 or EC1.2.1.2) of dependent form, NAD+The mannitol dehydrogenase (EC1.1.1.255) that relies on, one or more cells of nadh oxidase (EC1.6.3.4), and utilize NADH, NAD in cell+, NADPH and NADP+, and cell own metabolism regeneration of NAD+For NADH or NADP+For the cell own metabolism regenerating coenzyme system of NADPH, the living things catalysis system of composition.Or, can for being independent of the glucose isomerase of active somatic cell, the mannitol dehydrogenase of NAD (P) H dependence, NAD (P) for the living things catalysis system described in raw material production mannose with glucose or fructose+The hydrogenlyase of dependent form, NAD+Mannitol dehydrogenase, nadh oxidase and NADH, the NAD relied on+, NADPH and NADP+, the living things catalysis system of composition.
Accompanying drawing explanation
Fig. 1 reaction principle figure.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention will be further described.Should be understood that following example are merely to illustrate the present invention not for restriction the scope of the present invention.
As it is shown in figure 1, the production method of the mannose of the present invention, with glucose or fructose for substrate, by the mannitol dehydrogenase relied on by glucose isomerase, NAD (P) H, NAD (P)+The hydrogenlyase of dependent form, NAD+The living things catalysis system catalytic production mannose that mannitol dehydrogenase, nadh oxidase and the coenzyme relied on is constituted.
Embodiment 1
In aqueous systems, the whole mass concentration of glucose is 5%, and the whole mass concentration of sodium formate is 0.5%, nicotinamide adenine dinucleotide (NAD+) final concentration of 100mM, the final concentration of 100mM of NADPH (NADPH), adopt formic acid regulation and control reaction pH, reaction pH is 7.0, reaction temperature is 30 degree, the NADP in amount 1000U/L, the Burkholderiastabilis source of the mannitol dehydrogenase of the NADPH dependent form in amount 350U/L, the Agaricusbisporus source of the glucose isomerase in Streptomycesmurinus source+The NAD in amount 1000U/L, the Apiumgraveolens source of the nadh oxidase in amount 1000U/L, the Streptococcuspyogenes source of the hydrogenlyase of dependent form+The amount 1000U/L of the mannitol dehydrogenase relied on, reacts 12h, and in reaction system, mannose concentration is 3.5%.
Embodiment 2
Fructose concentration is 5%, and sodium formate concentrations is 0.5%, nicotinamide adenine dinucleotide (NAD+) concentration is 100mM, NADPH (NADPH) concentration is 100mM, adopt formic acid regulation and control reaction pH, reaction pH is 7.0, reaction temperature is 30 degree, the NAD (P) in mannitol dehydrogenase 1000U/L, the Burkholderiastabilis source of the NADP dependent form in Agaricusbisporus source+The NAD in nadh oxidase 1000U/L, the Apiumgraveolens source in hydrogenlyase 1000U/L, the Streptococcuspyogenes source of dependent form+The mannitol dehydrogenase 1000U/L relied on, reacts 12h, and in reaction system, mannose concentration is 4%.
Embodiment 3
Concentration of glucose is 5%, and fructose concentration is 5%, and sodium formate concentrations is 1%, nicotinamide adenine dinucleotide (NAD+) concentration is 100mM, NADPH (NADPH) concentration is 100mM, adopt formic acid regulation and control reaction pH, reaction pH is 7.0, reaction temperature is 30 degree, the NAD (P) in mannitol dehydrogenase 1000U/L, the Burkholderiastabilis source of the NADP dependent form in glucose isomerase 350U/L, the Agaricusbisporus source in Streptomycesmurinus source+The NAD in nadh oxidase 1000U/L, the Apiumgraveolens source in hydrogenlyase 1000U/L, the Streptococcuspyogenes source of dependent form+The mannitol dehydrogenase 1000U/L relied on, reacts 12h, and in reaction system, mannose concentration is 7%.
Claims (9)
1. the method for a Biological preparation mannose, it is characterised in that: with the one in a kind of in sodium formate or calcium formate or two kinds and glucose or fructose or two kinds for raw material;By the living things catalysis system that oxidoreductase and coenzyme are constituted, or the living things catalysis system that glucose isomerase, oxidoreductase and coenzyme are constituted, catalytic production mannose;Oxidoreductase is the mannitol dehydrogenase of NAD (P) H dependence, NAD (P)+The hydrogenlyase of dependent form, NAD+One or two or more kinds in the mannitol dehydrogenase of dependence, nadh oxidase.
2. the method for claim 1, it is characterized in that: described glucose isomerase, in aqueous systems, consumption is 0-100000U/L, zymetology classification number is EC5.3.1.5, is selected from: but it is not limited to the one in the glucose isomerase in the glucose isomerase in streptomyces source, the glucose isomerase in actinomyces source, bacillus source or two kinds.
3. the method for claim 1, it is characterized in that: the mannitol dehydrogenase that described NAD (P) H relies on is the NADH mannitol dehydrogenase relied on or the mannitol dehydrogenase of NADPH dependence, consumption 100U/L-1000000U/L in aqueous systems, zymetology classification number is EC1.1.1.138 and EC1.1.1.67, it is selected from: but it is not limited to the mannitol dehydrogenase in Agaricus source, the mannitol dehydrogenase in mycocandida source, the mannitol dehydrogenase in Lactobacillus source, the mannitol dehydrogenase in Leuconostoc source, Rhodopseudomonas source mannitol dehydrogenase in one or two kinds.
4. the method for claim 1, it is characterised in that: described NAD (P)+The hydrogenlyase of dependent form is NAD+The hydrogenlyase of dependent form or NADP+The hydrogenlyase of dependent form, in aqueous systems, consumption is 100U/L-1000000U/L, zymetology classification number is EC1.2.1.43, EC1.2.1.2, is selected from: but it is not limited to the one in the hydrogenlyase in the hydrogenlyase in mycocandida source, the hydrogenlyase in Burkholderia source, the hydrogenlyase in Rhodopseudomonas source, the hydrogenlyase in bacillus source, fusobacterium source or two kinds.
5. the method for claim 1, it is characterised in that: described NAD+The mannitol dehydrogenase relied on, in aqueous systems, consumption is 100U/L-1000000U/L, and zymetology classification number is EC1.1.1.255, is selected from: but it is not limited to the mannitol dehydrogenase in Herba Apii graveolentis source.
6. the method for claim 1, it is characterized in that: described nadh oxidase, consumption 100U/L-1000000U/L in aqueous systems, zymetology classification number is EC1.6.3.4, is selected from: but it is not limited to the one in Streptococcus nadh oxidase, Lactobacillus nadh oxidase, fusobacterium nadh oxidase or two kinds.
7. the method for claim 1, it is characterised in that: described coenzyme is NADH or NAD+In one or two kinds, and NADPH or NADP+In one or two kinds;NADH and NAD in system+Amount 5mM-500mM, NADPH and NADP in system+Amount 5mM-500mM.
8. the method for claim 1, it is characterized in that: in aqueous systems, the whole mass concentration of glucose or fructose is the whole mass concentration of 0.5-20%, sodium formate or calcium formate is 0.25%-2%, adopting formic acid regulation and control reaction pH=6-8, reaction temperature is 10-60 degree.
9. the method for claim 1, it is characterised in that described living things catalysis system can have, for expression, mannitol dehydrogenase, the NAD (P) that glucose isomerase, NAD (P) H rely on+The hydrogenlyase of dependent form, NAD+The mannitol dehydrogenase that relies on, one or more cells of nadh oxidase, and utilize NADH, NAD in cell+, NADPH and NADP+, and cell own metabolism regeneration of NAD+For NADH or NADP+For the cell own metabolism regenerating coenzyme system of NADPH, the living things catalysis system of composition;
Or, described living things catalysis system can be independent of the glucose isomerase of active somatic cell, the mannitol dehydrogenase of NAD (P) H dependence, NAD (P)+The hydrogenlyase of dependent form, NAD+Mannitol dehydrogenase, nadh oxidase and NADH, the NAD relied on+, NADPH and NADP+, the living things catalysis system of composition.
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Cited By (4)
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CN109097412A (en) * | 2018-07-24 | 2018-12-28 | 江苏理工学院 | A kind of method of bioanalysis synthesis Ezetimibe intermediate |
CN109837321A (en) * | 2017-11-29 | 2019-06-04 | 中国科学院大连化学物理研究所 | A kind of restoring method of NAD analog |
CN111808900A (en) * | 2019-04-12 | 2020-10-23 | 中国科学院大连化学物理研究所 | Method for reducing NAD analogue by formic acid |
CN112680482A (en) * | 2021-01-12 | 2021-04-20 | 中国科学院天津工业生物技术研究所 | Biological preparation method of mannitol |
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CN109837321A (en) * | 2017-11-29 | 2019-06-04 | 中国科学院大连化学物理研究所 | A kind of restoring method of NAD analog |
CN109837321B (en) * | 2017-11-29 | 2023-01-13 | 中国科学院大连化学物理研究所 | Reduction method of NAD analogue |
CN109097412A (en) * | 2018-07-24 | 2018-12-28 | 江苏理工学院 | A kind of method of bioanalysis synthesis Ezetimibe intermediate |
CN111808900A (en) * | 2019-04-12 | 2020-10-23 | 中国科学院大连化学物理研究所 | Method for reducing NAD analogue by formic acid |
CN111808900B (en) * | 2019-04-12 | 2023-06-20 | 中国科学院大连化学物理研究所 | Method for reducing NAD analogue by using formic acid |
CN112680482A (en) * | 2021-01-12 | 2021-04-20 | 中国科学院天津工业生物技术研究所 | Biological preparation method of mannitol |
CN112680482B (en) * | 2021-01-12 | 2022-12-20 | 中国科学院天津工业生物技术研究所 | Biological preparation method of mannitol |
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Application publication date: 20160706 |