WO2014185546A1 - グルコース製造方法およびこの方法により製造されたグルコース - Google Patents
グルコース製造方法およびこの方法により製造されたグルコース Download PDFInfo
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- WO2014185546A1 WO2014185546A1 PCT/JP2014/063173 JP2014063173W WO2014185546A1 WO 2014185546 A1 WO2014185546 A1 WO 2014185546A1 JP 2014063173 W JP2014063173 W JP 2014063173W WO 2014185546 A1 WO2014185546 A1 WO 2014185546A1
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/02—Monosaccharides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K1/00—Glucose; Glucose-containing syrups
- C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
Definitions
- the present invention relates to a glucose production method capable of improving the collection rate of glucose from a cellulose raw material, and glucose produced by this method.
- glucose has been increasingly used for industrial applications as a raw material for bioethanol and polymer materials as an alternative fuel for petroleum fuel.
- industrial glucose is potatoes and grains such as corn, wheat, barley, rye, triticale or rice, or plants for sugar raw materials such as sugar cane and sugar beet.
- potatoes and grains such as corn, wheat, barley, rye, triticale or rice
- sugar raw materials such as sugar cane and sugar beet.
- the transaction price of cereals and plants for sugar raw materials that are traded for food use has risen, and there are concerns over the impact on household pressure and hunger in developing countries. Has been.
- Patent Document 2 discloses glucose from such a cellulose raw material. Is described.
- an object of the present invention is to provide a glucose production method having excellent glucose collection rate and glucose produced by this method.
- ruminants such as cows, donkeys, camels, sheep and goats obtain energy by saccharifying cellulose raw materials such as rabbits.
- the present inventors pay attention to the cellulose degrading function of ruminants using cellulose raw material as food, find that the ruminant saliva is one factor that assists in enzymatic degradation, and complete the present invention. Arrived.
- a first aspect of the glucose production method of the present invention is characterized by decomposing cellulose using a mixture of a cellulolytic enzyme and an active aid derived from saliva or biological saliva.
- the saliva is the saliva of an animal that performs rumination
- the active aid derived from the biological saliva is extracted from the saliva of the animal that performs rumination. It is characterized by.
- a third aspect of the glucose production method of the present invention is characterized in that the saliva of the animal performing the rumination is bovine, donkey, camel, sheep, goat saliva.
- the glucose of the present invention is produced using the production method according to any one of the first to third aspects.
- Such glucose of the present invention is manufactured at a high collection rate from a cellulose raw material, so that it can be provided to the market at a low cost.
- the glucose production method of the present invention it is possible to dramatically improve the collection rate of glucose from a cellulose raw material.
- the cellulose raw material is saccharified by relatively gentle enzymatic degradation, the cost for manufacturing plant safety management can be reduced, and as a result, glucose can be provided at a low price. Make it possible.
- the glucose of the present invention it is possible to provide it to the market at a low cost by being manufactured from a cellulose raw material at a high collection rate.
- the flowchart which shows the manufacturing process in embodiment of the glucose manufacturing method of this invention.
- the graph which shows the glucose collection amount of each sample in Example 1 of the glucose manufacturing method of this invention
- the graph which shows the glucose collection amount of each sample in Example 2 of the glucose manufacturing method of this invention
- the graph which shows the glucose collection amount of each sample in Example 3 of the glucose manufacturing method of this invention
- the graph which shows the glucose collection amount of each sample in Example 4 of the glucose manufacturing method of this invention
- the graph which shows the glucose collection amount of each sample in Example 5 of the glucose manufacturing method of this invention
- the graph which shows the glucose collection amount of each sample in Example 6 of the glucose manufacturing method of this invention
- the graph which shows the glucose collection amount of each sample in Example 7 of the glucose manufacturing method of this invention
- the graph which shows the glucose collection amount of each sample in Example 8 of the glucose manufacturing method of this invention
- Silver-stained image of each eluate with molecular size fractionation The graph which shows the glucose collection amount of each sample in Example 9 of the glucose manufacturing method of this invention
- the glucose production method of the present invention is a method for obtaining glucose by decomposing cellulose raw materials such as wood, grass and rice straw using a mixture of a cellulose-degrading enzyme and an active aid derived from saliva or biological saliva.
- Cellulose-degrading enzyme is an endoglucanase that randomly cuts non-crystalline regions of cellulose and lowers the degree of polymerization of cellulose, cellobiohydrolase that degrades by cellobiose from the end of the crystalline region of cellulose, and ⁇ - that degrades cellobiose into glucose Cellulase containing three kinds of enzymes, glucosidase, can be used.
- the cellulase is not particularly limited, such as a commercially available cellulase or a product extracted from bacteria or plants. However, by using a cellulase derived from Trichoderma that is excellent in cellulose degradation, the glucose collection rate is further improved. Can be made.
- the saliva of an animal that performs rumination or the active aid extracted from the saliva can be used.
- animals that perform rumination include cattle, donkeys, camels, sheep, and goats.
- a predetermined amount of saliva can be stably supplied by applying cattle.
- organic compounds in biological saliva can be used.
- An enzymatic decomposition step S2 for performing enzymatic decomposition with a mixture of saliva or a living saliva-derived active assistant, and a glucose purification step S3 for purifying glucose generated in the enzymatic decomposition step S2 are performed.
- the pulverization step S1 can be omitted when the particle size of the cellulose raw material C is sufficiently fine.
- a liquefaction step of imparting fluidity to cellulose by dissolving it in an ionic liquid or dissolving it in a basic solvent such as ethylenediamine can be employed.
- glucose is produced from the cellulose raw material C by enzymatic decomposition, and in the enzymatic decomposition step S2, the cellulose-degrading enzyme and the active aid derived from saliva or biological saliva are used.
- the cellulose-degrading enzyme and the active aid derived from saliva or biological saliva are used.
- the cellulose raw material is saccharified by relatively gentle enzymatic decomposition, the cost for safety management of the production plant can be reduced, and as a result, the produced glucose is provided at a low price. It is possible to do.
- Example 1 glucose was produced using bovine saliva as the saliva of the organism.
- Avicel manufactured by Merck
- the cellulolytic enzyme is cellulase (Trichoderma Viride (Sigma-Aldrich)).
- 500 ⁇ g of cellulase is suspended in 1 mL of 50 mM buffer, and further diluted 5-fold with the buffer to obtain a 100 ⁇ g / mL enzyme solution.
- bovine saliva a stock solution obtained by diluting a bovine mouth with a buffer solution 50-fold diluted with a buffer solution was used, both of which were sodium acetate aqueous solution with pH 4.0.
- sample A 15 ⁇ L of a 100 ⁇ g / mL enzyme solution and 15 ⁇ L of bovine saliva are added to 120 ⁇ L of a 10 ⁇ g / mL substrate suspension as cellulose raw material C, and the condition is 24 hours at 50 ° C. (This sample is hereinafter referred to as sample A).
- Sample D made up to 150 ⁇ L was also incubated for 24 hours at 50 ° C., respectively.
- FIG. 2 shows the results of calculating the reducing sugar concentration using the Somogi-Nelson method after incubation.
- the sample A using the glucose production method of the present invention was 0.32 mg / mL
- the sample B in which only cellulase was added to the cellulose raw material C was 0.06 mg / mL.
- 0.02 mg / mL of reducing sugar was detected for sample C in which only bovine saliva was added to cellulose raw material C, and 0.02 mg / mL for sample D of cellulose raw material C alone.
- the value shown in FIG. 2 is an average value of three samples, and the standard deviation is shown as an error bar.
- Example 2 glucose was generated using an active aid solution obtained by extracting an organic compound from bovine saliva as an active aid derived from biological saliva.
- Example 1 Using a total of 8 types of active aid solutions purified from bovine saliva, the glucose production method of the present invention described in detail in Example 1 was used to produce glucose using the active aid solution instead of bovine saliva. It was.
- sample 1 has a methanol concentration of about 5%
- sample 2 has a methanol concentration of about 21%
- sample 3 has a methanol concentration of about 37%
- sample 4 has a methanol concentration of about 53%
- sample 5 has a methanol concentration of about 5%.
- sample 6 is a methanol concentration of about 84%
- sample 7 is a methanol concentration of about 100%
- sample 8 is an active auxiliary solution separated when the methanol concentration is 100% (water 0%).
- the glucose raw material and cellulose degrading enzyme used were those described in Example 1.
- 0.03 mg / mL for sample 3 of this sample 0.05 mg / mL for sample 4 with a methanol concentration of about 53%, 0.07 mg / mL for sample 5 with a methanol concentration of about 68%, and a sample with a methanol concentration of about 84% 0.28 mg / mL for sample 6, 0.31 mg / mL for sample 7 with a methanol concentration of about 100%, 0.09 mg / mL for sample 8 with a methanol concentration of 100% (water 0%), and only cellulase as the cellulose raw material In sample 9 to which was added 0.03 mg / mL of reducing sugar was detected.
- the value shown in FIG. 3 is an average value of three samples, and the standard deviation is shown as an error bar.
- Sample 6 having a methanol concentration of about 84% and Sample 7 having a methanol concentration of about 100% show extremely high reducing sugar concentrations, and based on this result, an active aid containing an organic compound eluted at a methanol concentration of 84% or more. It is clear that the solution promotes enzyme activity.
- Example 3 In Example 3, the production of glucose was performed using the saliva of donkey as the saliva of the organism. For comparison, glucose was also produced using bovine saliva under the same conditions.
- Example 2 As the cellulose raw material and the cellulose-degrading enzyme, those described in Example 1 were used. In this example, 500 ⁇ g of cellulase was suspended in 1 mL of 50 mM buffer solution, and further used as a 50 ⁇ g / mL enzyme solution diluted 10-fold with the buffer solution.
- Example 4 In Example 4, in order to examine the relationship between the concentration of bovine saliva and the amount of collected glucose, glucose was produced from 0 to 10% concentration of bovine saliva, with the bovine saliva stock solution being 100%.
- Example 2 As the cellulose raw material and the cellulose-degrading enzyme, those described in Example 1 were used. The stock solution is diluted with the buffer so that bovine saliva is 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, and 10%, respectively. Used.
- the collected amount of glucose increased rapidly up to a saliva concentration of 2%, and almost the same amount of glucose was collected at a saliva concentration of 2% to 10%.
- Example 5 In Example 5, in order to examine the relationship between the incubation time and the collected amount of glucose, glucose was produced by changing the incubation time between 0 and 72 hours.
- cellulose raw material As the cellulose raw material, cellulose-degrading enzyme, and bovine saliva, those described in Example 1 were used. Then, as a comparative sample, glucose was generated by adding only a cellulose-degrading enzyme to a cellulose raw material as a substrate.
- the amount of collected glucose increased as the incubation time increased.
- the glucose collection amount did not depend on the incubation time.
- the amount of glucose collected by the sample using the glucose production method of the present invention was about 30 times that of the sample to which only the cellulolytic enzyme was added.
- Example 6 carboxymethyl cellulose (CMC, manufactured by Nacalai Techs) was used as a cellulose raw material in order to examine the amount of glucose produced when the glucose production method of the present invention was applied to a water-soluble cellulose raw material. Glucose was produced.
- CMC carboxymethyl cellulose
- the cellulose-degrading enzyme and bovine saliva used were those described in Example 1. Then, as a comparative sample, glucose was generated by adding only a cellulose-degrading enzyme to a cellulose raw material as a substrate.
- glucose production method in this example first, 20 ⁇ L of 100 ⁇ g / mL enzyme solution and 20 ⁇ L of bovine saliva were added to 160 ⁇ L of 10 ⁇ g / mL substrate suspension as cellulose raw material C, and 30 minutes at 50 ° C. Incubation was performed.
- FIG. 7 shows the results of calculating the reducing sugar concentration using the Somogi-Nelson method after incubation. Note that glucose was also produced by the same production method for the sample in which only the cellulolytic enzyme was added to the cellulose raw material.
- the glucose production method of the present invention was applied, 0.17 mg / mL for the sample to which bovine saliva was added, only cellulolytic enzyme was added, and bovine saliva was added. For samples that did not, 0.0075 mg / mL glucose was obtained.
- Example 7 In Example 7, the specific effect of bovine saliva will be described. As a preliminary experiment, the present inventors examined the influence of bovine saliva on the crystal form of the cellulose raw material, and it became clear that bovine saliva does not affect the crystal form of the cellulose raw material. Furthermore, the static surface tension of bovine saliva was measured, and it was revealed that bovine saliva has a surface-active action.
- samples (i) to (c) with different timings of adding bovine saliva were examined.
- bovine saliva was added to the cellulose raw material and incubated at 50 ° C. for 1 hour, followed by addition of cellulose-degrading enzyme and incubation at 50 ° C. for 24 hours. Generated.
- sample (b) cellulose-degrading enzyme is added to the cellulose raw material, incubated for 1 hour at 50 ° C, and then bovine saliva is added and incubated for 24 hours at 50 ° C to produce glucose. went.
- bovine saliva was added to the cellulolytic enzyme and incubated for 1 hour at 50 ° C., followed by addition of the cellulose raw material and incubation for 24 hours at 50 ° C. Generated.
- glucose was produced in quantities of 160 ⁇ L of 10 ⁇ g / mL substrate suspension as cellulose raw material C, 20 ⁇ L of 100 ⁇ g / mL enzyme solution and 20 ⁇ L of bovine saliva.
- FIG. 8 shows the result of calculating the reducing sugar concentration after incubation using the Somogi-Nelson method.
- bovine saliva does not affect the crystal form of the cellulose raw material, it was adsorbed on the surface of the cellulose raw material and added in the subsequent process because the sample (a) had the largest amount of glucose collected. It turns out that the effect
- Example 8 In Example 8, in order to examine in more detail the characteristics of biological saliva-derived active assistants, glucose was generated using an active assistant solution obtained by denaturation and molecular weight fractionation of bovine saliva.
- a centrifugal filter (UFC910024, manufactured by Millipore) using an ultrafiltration membrane with a cutoff molecular weight cut value of 100K was used for 2 mL of sample A at 3000 rpm.
- Molecular weight fractionation was performed by high-speed centrifugation at 15 ° C. for 15 minutes to obtain an active assistant solution (sample B) having a molecular weight of 100K or less.
- glucose in this example In the production method of glucose in this example, first, 160 ⁇ L of 10 ⁇ g / mL substrate suspension as cellulose raw material C, 20 ⁇ L of 100 ⁇ g / mL enzyme solution as cellulose-degrading enzyme and ethanol-denaturing activity assistant as sample A 20 ⁇ L of the solution was added, and incubation was performed at 50 ° C. for 24 hours. After incubation, the reducing sugar concentration was calculated using the Mogi-Nelson method. In addition, the cellulose raw material C and the cellulose degrading enzyme described in Example 1 were used.
- sample A was changed to samples B to D, respectively, and the results obtained are shown in FIG.
- FIG. 9 in order to examine the effects of each of the samples A to D, the result of calculating the reducing sugar concentration by similarly producing glucose using untreated bovine saliva is shown as “bovine saliva”.
- the result of calculating glucose concentration by producing glucose without using bovine saliva is shown as “no bovine saliva”.
- the reducing sugar concentration when using sample A as the ethanol-denaturing activity auxiliary solution shows almost the same value as the reducing sugar concentration when using untreated bovine saliva.
- the enzyme having activity contained in bovine saliva is not a causative substance that promotes the enzyme activity of cellulolytic enzyme.
- the reducing sugar concentration when using Sample D as an active aid solution having a molecular weight of 3K or less is lower than the reducing sugar concentration without bovine saliva, the molecular weight contained in bovine saliva
- organic polymers of 3K or less are not causative substances that promote the enzyme activity of cellulolytic enzymes. From the above results, it has been clarified that the active assistant derived from bovine saliva is an organic polymer having a molecular weight of 3K or more including a denatured protein.
- Example 9 In Example 9, in order to specify the component of the active aid derived from biological saliva, glucose produced by using a solution obtained by subjecting bovine saliva to molecular size fractionation by gel filtration chromatography was used as an active aid solution. It was.
- molecular size fractionation was performed on 4 mL of bovine saliva using a liquid chromatography apparatus (AKTAprime, manufactured by GE Healthcare). Chromatographic conditions are as follows. Sample: Bovine saliva Sample injection volume: 4 mL Column: HiLoad 16/600 Superdex 200 prep grade (manufactured by GE Healthcare) Eluent: 150 mM sodium chloride aqueous solution Flow rate: 1 mL / min Eluate fractionation: 5 mL x 24 (Fraction No. 1 to 24) In the following, the fractionated 24 eluates are fraction No. 1 to 24.
- the protein concentrations of the obtained samples A to E and Mix elution concentrate and saliva stock solution were measured.
- the protein concentration of each sample was 201.8 ⁇ g / mL for sample A, 174.5 ⁇ g / mL for sample B, C was 108.6 ⁇ g / mL, Sample D was 795.7 ⁇ g / mL, Sample E was 276.9 ⁇ g / mL, Sample Mix was 366.2 ⁇ g / mL, and Saliva Stock Solution was 1214.2 ⁇ g / mL.
- a cellulolytic enzyme activity measurement test was performed using an elution diluted solution and a saliva solution prepared by adjusting the elution concentrated solution and saliva stock solution of each of these samples to a protein concentration of 40 ⁇ g / mL with ultrapure water.
- the glucose produced using the elution dilutions and the saliva solution of Samples A to E and Sample Mix is higher than that produced using only the enzyme.
- the glucose concentration is shown, and it was confirmed that the activity of cellulolytic enzyme was promoted by adding each elution dilution and saliva. From this, it was clarified that the biological saliva-derived activity assistant that promotes the enzyme activity of cellulolytic enzyme is a protein.
- the biological saliva-derived activity assistant that promotes the enzyme activity of cellulolytic enzyme is a protein.
- an activity promoting effect can be obtained regardless of the type of protein contained in the biological saliva. It was.
- the glucose production method of the present invention relates to a method for producing glucose by enzymatic decomposition of cellulose raw material C, and in addition to cellulose-degrading enzyme, biological saliva or an active assistant derived from biological saliva is added.
- cellulose-degrading enzyme biological saliva or an active assistant derived from biological saliva is added.
- the glucose production method of the present invention is not limited to the above-described embodiment, and various modifications such as cellulolytic enzyme, ruminant saliva, and activity derived from biological saliva are within the range not impairing the features of the invention.
- Cellulose may be enzymatically decomposed using a mixture of all the auxiliaries, and the activity of the cellulolytic enzyme can be further improved by combining saliva and an active auxiliary derived from biological saliva.
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Abstract
Description
実施例1においては、生物の唾液としてウシの唾液を用いてグルコースの生成を行った。
実施例2においては、生物唾液由来の活性助剤としてウシ唾液から有機化合物を抽出した活性助剤溶液を用いてグルコースの生成を行った。
実施例3においては、生物の唾液としてロバの唾液を用いてグルコースの生成を行った。なお、比較として、同じ条件にてウシの唾液を用いたグルコースの生成も行った。
実施例4においては、ウシ唾液の濃度とグルコースの収集量の関係を検討するべく、ウシ唾液の原液を100%とした0~10%の濃度のウシ唾液についてグルコースの生成を行った。
実施例5においては、インキュベーション時間とグルコースの収集量との関係を検討するべく、インキュベーション時間を0~72時間の間で変化させてグルコースの生成を行った。
実施例6においては、水溶性のセルロース原料に対して、本発明のグルコース製造方法を適用した場合のグルコースの生成量を検討するべく、セルロース原料としてカルボキシメチルセルロース(CMC、ナカライテクス社製)を用いてグルコースの生成を行った。
実施例7においては、ウシ唾液の具体的な作用効果について説明する。なお、本発明者等は予備的な実験として、ウシ唾液のセルロース原料の結晶形への影響を検討したところ、ウシ唾液はセルロース原料の結晶形には影響を与えないことが明らかとなった。さらに、ウシ唾液の静的表面張力を測定して、ウシ唾液が界面活性作用を有していることが明らかとなった。
実施例8においては、生物唾液由来の活性助剤の特性をより詳細に検討するべく、ウシ唾液の変性および分子量分画を行ったものを活性助剤溶液として用いグルコースの生成を行った。
実施例9においては、生物唾液由来の活性助剤の成分を特定するべく、ウシ唾液に対してゲル濾過クロマトグラフィーによる分子サイズ分画を行ったものを活性助剤溶液として用いグルコースの生成を行った。
試料:ウシ唾液
試料注入量:4mL
カラム:HiLoad 16/600 Superdex 200 prep grade(GE Healthcare社製)
溶離液:150mM塩化ナトリウム水溶液
流速:1mL/min
溶出液分取:5mL×24本(Fraction No.1~24)
なお、以降、分取した24本の溶出液は、それぞれFraction No.1~24と称する。
基質:2wt%基質/100mM酢酸ナトリウム緩衝液(pH=4.0)
セルロース分解酵素:100μg/mLのCellulase from Trichderma Viride(SigmaAldrih社製)
唾液溶液:40μg/mL
溶出希釈液:タンパク質濃度40μg/mLのサンプルA~EおよびサンプルMix
S2 酵素分解工程
S3 グルコース精製工程
C セルロース原料
Claims (4)
- セルロースを、セルロース分解酵素と、唾液または生物唾液由来の活性助剤との混合物を用いて分解することを特徴とするグルコース製造方法。
- 前記唾液が、反芻を行う動物の唾液であり、
前記生物唾液由来の活性助剤が、反芻を行う動物の唾液から抽出されてなることを特徴とする請求項1に記載のグルコース製造方法。 - 前記反芻を行う動物の唾液が、ウシ、ロバ、ラクダ、ヒツジ、ヤギの唾液であることを特徴とする請求項1または請求項2に記載のグルコース製造方法。
- 請求項1乃至請求項3のいずれかの製造方法を用いて製造されたことを特徴とするグルコース。
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US14/891,952 US10119156B2 (en) | 2013-05-17 | 2014-05-19 | Glucose production method and glucose produced by said method |
KR1020157035081A KR20160011192A (ko) | 2013-05-17 | 2014-05-19 | 글루코스 제조 방법 및 이 방법으로 제조된 글루코스 |
EP14797675.7A EP2998403A4 (en) | 2013-05-17 | 2014-05-19 | PROCESS FOR PRODUCING GLUCOSE AND GLUCOSE THUS OBTAINED |
CN201480028197.8A CN105408491B (zh) | 2013-05-17 | 2014-05-19 | 葡萄糖制造方法以及通过该方法制造的葡萄糖 |
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JP2014-097515 | 2014-05-09 | ||
JP2014097515A JP6440966B2 (ja) | 2013-05-17 | 2014-05-09 | グルコース製造方法 |
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WO2011111664A1 (ja) * | 2010-03-08 | 2011-09-15 | 独立行政法人森林総合研究所 | リグニン系酵素安定化剤 |
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WO2011111664A1 (ja) * | 2010-03-08 | 2011-09-15 | 独立行政法人森林総合研究所 | リグニン系酵素安定化剤 |
JP2012085544A (ja) | 2010-10-15 | 2012-05-10 | Taisei Corp | 草本系バイオマスの糖化方法 |
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Title |
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BORJESSON,J ET AL.: "Enhanced enzymatic conversion of softwood lignocellulose by poly (ethylene glycol) addition.", ENZYME MICROB. TECHNOL., vol. 40, no. 5, pages 754 - 762, XP005892495 * |
See also references of EP2998403A4 * |
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EP2998403A1 (en) | 2016-03-23 |
US20160090613A1 (en) | 2016-03-31 |
KR20160011192A (ko) | 2016-01-29 |
CN105408491A (zh) | 2016-03-16 |
CN105408491B (zh) | 2019-11-12 |
JP6440966B2 (ja) | 2018-12-19 |
EP2998403A4 (en) | 2016-06-01 |
JP2015116184A (ja) | 2015-06-25 |
US10119156B2 (en) | 2018-11-06 |
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