[go: up one dir, main page]

WO1986004353A1 - Procede de regeneration intrasequentielle du co-facteur lors de syntheses enzymatiques, en particulier lors de la production de vitamine c - Google Patents

Procede de regeneration intrasequentielle du co-facteur lors de syntheses enzymatiques, en particulier lors de la production de vitamine c Download PDF

Info

Publication number
WO1986004353A1
WO1986004353A1 PCT/EP1986/000024 EP8600024W WO8604353A1 WO 1986004353 A1 WO1986004353 A1 WO 1986004353A1 EP 8600024 W EP8600024 W EP 8600024W WO 8604353 A1 WO8604353 A1 WO 8604353A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
enzymatically
dehydrogenase
oxidation
lactone
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1986/000024
Other languages
German (de)
English (en)
Inventor
Klaus D. Kulbe
Gisela Knopki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Original Assignee
Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV filed Critical Fraunhofer Gesellschaft zur Foerderung der Angewandten Forschung eV
Publication of WO1986004353A1 publication Critical patent/WO1986004353A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
    • 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
    • C12P1/00—Preparation of compounds or compositions, not provided for in groups C12P3/00 - C12P39/00, by using microorganisms or enzymes
    • 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
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • C12P7/18—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic polyhydric
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/58—Aldonic, ketoaldonic or saccharic acids
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/58—Aldonic, ketoaldonic or saccharic acids
    • C12P7/60—2-Ketogulonic acid
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

  • the invention relates to a method for intrasequen. tial cofactor regeneration in two- or multi-stage enzymatic syntheses.
  • the invention relates in particular to processes for the production of vitamin C or L-ascorbic acid and for the production of intermediate products which can be used for the production of vitamin C.
  • DE-OS 33 26 546.1-42 (1983) describes for the first time a technically interesting process in which two mixtures of glucose and fructose, as are also produced on an industrial scale from sucrose on an industrial scale, are simultaneously economical interesting products can be obtained. While glucose is oxidized to gluconic acid by glucose dehydrogenase, fructose in one of sorbitol or
  • L-ascorbic acid (vitamin C) is still produced on an industrial scale using the chemical synthesis method developed by T. Reichstein and A. Grüssner (Helv. Chi. Acta V7, 311 (1934)), starting from D-glucose.
  • US Pat. No. 2,681,858 describes the enzymatic cleavage of lactose by 3-galactosidase in D-galactose and D-glucose.
  • the conversion of glucose and galactose into the corresponding uronic acid or uronic acid derivatives using protective groups is also known: (US Pat. No. 4,259,443 1981; CL Mehltretter et al. J. Amer. Chem. Soc. 73_, 2424 (1951)).
  • the yields of uronic acids obtained in this known process are too low for an economical one US Pat. No. 4,259,443 describes a process for the production of L-ascorbic acid from lactose
  • the object 5 f Jer present invention is based on a comparison fanren for the production of vitamin C to provide, in the cecni ⁇ cneii. and can be carried out on a technical scale, with ⁇ er enzymes used as catalysts and which enables the regeneration of the required * - * 1 cofactors.
  • the process according to the invention, in which enzymes are used, should be able to be carried out in an economical manner without incurring unacceptable losses. It should give the desired product in high yields. b
  • a purely enzymatic process for the production of L-ascorbic acid from D-galacturonic acid or D-glucuronic acid or mixtures of D-glucuronic acid and D-galacturonic acid is to be made available.
  • a method is to be made available according to which these uronic acids from lactose or other easily accessible starting materials, e.g. Glucose, pectin, alginic acid or gluconic acid can be obtained economically.
  • inventive method in particular the process for the production of vitamin C or step his Vor ⁇ or intermediate products, shall be characterized by the following advantages:
  • the invention relates to a method for intrasequen ⁇ tial cofactor regeneration in enzymatic syntheses, which is characterized in that a substrate is enzymatically reduced in the same reactor or in separate stages (D) and the reduction product obtained is converted enzymatically into an oxidation product or (2 ) enzymatically oxidizes a Sunstrat and " enzymatically converts the oxidation product obtained into a reduction product and isolates the desired end product in a manner known per se, where two enzymes are used for the coupled oxidation and reduction, which have the same cofactor specificity. (This process is illustrated in Figures 1 and 3 to 8 using some examples.)
  • the following reaction scheme shows the enzymatic production process for L-sorbose from D-glucose with intra-sequential cofactor (here NAD / NADH 2 > regeneration).
  • FIGS. 6 and 8 show the enzymatic reactions in more detail.
  • the process according to the invention has the great advantage that it can be carried out continuously and on a semi-technical as well as on an industrial scale.
  • the process according to the invention has the essential advantage that the co-actuators can be regenerated in a simple manner, that inexpensive substrates can be used and that the substrates are fully utilized.
  • the end product obtained has a high degree of purity, so that little or no by-products are formed and the environmental impact is very low. The investment east is also low.
  • the oxidation-reduction reactions are carried out under the reaction conditions normally used for carrying out enzymatic reactions, for example the pH is generally between 5 and 9, preferably between 6 and 8.
  • L-hexonate dehydrogenase, aldose reductase, mannuronate dehydrogenase or lactate dehydrogenase can be used as the reducing enzyme, and L-galactonic acid (L-gulonic acid) -lactone dehydrogenase and L-galactonic acid (L -Gulonic acid) - lactonase and inositol-1-phosphate synthase, fructuronate dehydrogenase or malate dehydrogenases can be used.
  • the cofactor is only used in the process according to the invention in catalytic amounts and it can be used in * free form or bound to soluble polymers or to enzymes.
  • the enzymes can be used in free or in immobilized form.
  • Fe + / Fe + complexes such as K Fe (CN) g / K 4 Fe (CN) 6 or cytochlorne c,
  • T-naphthoquinone ß-naphthoquinone, naturally occurring or synthetic redox dyes, such as 2, 6-dichlorophenolindophenol, o-chlorophenolindo-2,6-dichlorophenol, methylene blue, Wurster's blue, triphenyl-tetrazolium chloride, phenzin methosulfate,
  • Coenzymes such as NAD NADH 2 , NADP / DPH 2 , Q0, Q2, Q6, Q7,
  • the redox systems nicotinamide adenine dinucleotide (NAD / NADH-) or nicotinamide adenine dinucleotide phosphate (NADP + / NADPH 2 ), Fe + / Fe-cyto-chromium c, 2, 6-dichlorophenol-indophenol or are preferred Phenazine ethosulfate used.
  • the method according to the invention is particularly well suited for the enzymatic production of vitamin C. As shown in FIG. 2, the following starting materials can be used.
  • FIG. 7 shows a further synthetic route, which starts from D-gluconic acid.
  • the homo- or heteropolyglycans containing galacturonic acid or D-galacturonic acid or mannuronic acid are hydrolyzed chemically or enzymatically (cf. FIG. 1).
  • the homopolymers or heteropolymers containing D-galactose or D-glucose or D-mannose are oxidized chemically, microbiologically or enzymatically to the corresponding compounds containing D-galacturonic acid or D-glucuronic acid or D-mannuronic acid and then hydrolyzed.
  • pectin As an advantageous raw material for the production of L-ascorbic acid, pectin comes into question, which is found to 15 to 30% in the middle lamella of plant cell walls.
  • This pectin (for example from sugar beet chips) is used to produce D-galacturonic acid by attacking pectin methyl esterases, endo- and exo-polygalacturonases, preferably in the pH range 4 to 6.
  • the Enzymlessnesspara- used 'te need to achieve a high yield of D-Ga ⁇ lacturonklaire necessarily be lyaseok, otherwise ⁇ -4-5-unsaturated D-galacturonic acid-derivatives are formed which are not reacted further to L-ascorbic acid NEN kön ⁇ .
  • Hexuronate reductase (EC 1.1.1.19) gives L-galactone acid, the ⁇ -lactose of which can preferably be further reacted enzymatically-oxidatively to give 2-keto-L-galactonic acid (or its ⁇ -lactone). In a known, non-enzymatically catalyzed manner, this compound gives L-ascorbic acid by rearrangement (cf. FIG. 1).
  • the disaccharides are chemically, enzymatically or microbiologically oxidized and then enzymatically following 'table or chemically hydrolyzed or they are enzymatically or chemically cleaved into their monomeric constituents.
  • the monosaccharides are oxidized enzymatically or chemically to the corresponding uronic acids.
  • the chemical process requires the introduction and later removal of protective groups.
  • Starch, maltose, cellobiose or sucrose are enzymatically converted into myo-inositol and then enzymatically oxidized to D-glucuronic acid via glucose-1-phosphate.
  • the invention further relates to a process for the preparation of L-ascorbic acid, in which D-galacturonic acid or D-glucuronic acid or a mixture of these two acids is used as the substrate.
  • a mixture of these two acids is obtained, for example, by chemical or enzymatic oxidation together with hydrolysis from lactose.
  • the two acids mentioned or the mixture of the acids are enzymatically reduced to L-galactonic acid or L-gulonic acid or a mixture of these acids, and these are optionally converted into their lactones or a mixture of the lactones.
  • the acids or a mixture of the acids or the lactones or a mixture of the lactones are then oxidized enzymatically to the corresponding 2-keto acids and rearranged to ascorbic acid, which is isolated in a manner known per se.
  • a mixture of D-galacturonic acid and D-glucuronic acid is obtained from lactose by chemical or enzymatic oxidation in combination with a hydrolysis step.
  • a mixture of L-galactonic acid and L-gulonic acid is generated from these two D-uronic acids with configuration reversal (inversion).
  • the 2-keto-L-galactonic acid and 2-keto-L-gulonic acid or their y-lactones (stage 3) obtainable therefrom by enzymatic oxidation go uncatalyzed into L-ascorbic acid (vitamin C).
  • the reduction step (step 2, E., ) and the oxidation step (step 3, E ' 2 ) can be linked together to form a continuous process.
  • a continuous regeneration of the in -E or E-, catalyzed individual steps each required coenzymes (redox systems), so that they only need to be used in catalytic amounts.
  • the end products obtained in the process according to the invention can be separated off in a manner known per se and must be removed from the equilibrium. They can be separated or isolated, for example, by absorption chromatography, distribution chromatography, ion exchange chromatography, fractional crystallization, electrodialysis or electrodialytic focusing.
  • the D-glucuronic acid used in the process for the production of vitamin C described above can also be added according to the invention by enzymatic reduction of D-mannuronic acid to D-mannonic acid and subsequent oxidation of the D-mannonic acid to D-fructuronic acid and isomerization of the D-fructuronic acid D-glucuronic acid can be produced.
  • alginic acid can also be used as an inexpensive starting material (cf. FIG. 3).
  • L-sorbose is an intermediate for the production of vitamin C, and this compound can be made from D-glucose or from D-fructose. D-glucose or D-fructose are enzymatically reduced to D-sorbitol, and D-sorbitol is enzymatically oxidized to L-sorbose (see FIG. 6.8).
  • the D-forms can be converted into the desired L-form in an enzymatic manner. Such conversions are otherwise difficult to achieve and are therefore carried out microbiologically in the Reichstein synthesis (cf. the reaction schemes above).
  • the oxidation-reduction reactions according to the invention can be carried out, for example, in a reactor with an ultrafiltration membrane, using a cofactor system which is bound to a water-soluble polymer with an average molecular weight between 5000 and 30,000 daltons. A pressure difference is generated across the membrane of the reactor, and a product stream is continuously removed behind the membrane.
  • hollow fibers can be used as membranes whose structure is asymmetrical, the selective layer of the membrane impermeable to enzymes and polymer-bound coenzymes lying on the outside of the hollow fiber, while the inside of the fiber contains pores which are also suitable for the Enzymes and coenzymes are permeable.
  • the substrate solution is then introduced on the inside of the hollow fiber membrane, a hydrostatic pressure difference is generated between the inner and outer wall of the fiber, so that the substrate solution passes through the inner fiber wall and the enzymatic reactions preferably take place in the porous support material between the inner wall and the outer wall.
  • the throughput of the substrates can be adjusted so that their residence time in the hollow fiber wall is sufficient to achieve the most complete possible implementation.
  • the actual un twist ⁇ permeable to enzymes and polymer-bound cofactors selective layer of the membrane can lie on the inside of the hollow fiber and effect the enzymatic reaction in ⁇ lumen of the hollow fiber.
  • a protective protein can be added to the reaction solution in an amount
  • the mixture of residual substrate, product, enzyme and cofactor can also be flowed through a membrane module 5, the membrane pores of which are designed in such a way that they only allow the product and residual substrate to pass through, but retain the remaining components, the latter being returned to the reactor .
  • the enzymes present together in the reactor can have different half-lives of their inactivation. In order to keep the reactor functional over a longer period of time, the enzymes are kept in an activity ratio between the reactor
  • the substrate turnover rates per unit of time can also be changed from forward and backward through additional dosing of individual dissolved enzymes or the cofactor during the production process.
  • Some of the enzymes required are, as in the case of sorbitol dehydrogenase (EC 1.1.1.14) from sheep's liver or Candida utilis, or lactate dehydrogenase
  • the other enzymes can be e.g. Isolate from the following sources:
  • Sorbitol DH EC 1. 1 . 1 . 1 4 Lactobacillus brevis, (Iditol-DH) Zymomonas mobilis, Gluconobacter xylinum Acetobacter suboxydans
  • L-hexonate dehydrogenase 1. 1 . 1 .20 Erwinia carotevora, Euglenia gracilis, Erb sen, S. cerevisiae, Saccharomyces lipolytic Lipomyces starkeyi, Schwanniomyces oc ⁇ iden talis, Aspergillus nige and others.
  • Yeast Yeast
  • Lactobacillus brevis Lactobacillus brevis, E. coli
  • Aerobacter Aerobacter, Aeromonas, Bacterium, Bacteroides Klebsiella, Vibrio

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Mycology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)

Abstract

Procédé de régénération intraséquentielle du co-facteur lors de synthèses enzymatiques à une ou plusieurs étapes. Par ce procédé, un substrat est réduit par des enzymes dans un même système de réaction (à une ou plusieurs étapes), et le produit de réduction ainsi obtenu est transformé par des enzymes en un produit d'oxydation, ou un substrat est oxydé par des enzymes, et le produit d'oxydation ainsi obtenu est transformé par des enzymes en un produit de réduction. Le produit final voulu est isolé par des procédés connus, tandis que l'on utilise pour les procédés associés d'oxydation et de réduction deux enzymes présentant la même spécificité pour ce qui est du co-facteur. Le procédé convient particulièrement bien pour la production de vitamine C, de ses produits intermédiaires ou de ses précurseurs.
PCT/EP1986/000024 1985-01-23 1986-01-22 Procede de regeneration intrasequentielle du co-facteur lors de syntheses enzymatiques, en particulier lors de la production de vitamine c Ceased WO1986004353A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853502141 DE3502141A1 (de) 1985-01-23 1985-01-23 Verfahren zur intrasequentiellen cofaktor-regeneration bei enzymatischen synthesen, insbesondere bei der herstellung von vitamin c
DEP3502141.1 1985-01-23

Publications (1)

Publication Number Publication Date
WO1986004353A1 true WO1986004353A1 (fr) 1986-07-31

Family

ID=6260543

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1986/000024 Ceased WO1986004353A1 (fr) 1985-01-23 1986-01-22 Procede de regeneration intrasequentielle du co-facteur lors de syntheses enzymatiques, en particulier lors de la production de vitamine c

Country Status (4)

Country Link
EP (1) EP0209583A1 (fr)
JP (1) JPS62501747A (fr)
DE (1) DE3502141A1 (fr)
WO (1) WO1986004353A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997029194A3 (fr) * 1996-02-09 1997-10-02 Herbstreith & Fox Kg Pektin Fa Preparation d'acide l-ascorbique
WO2013117585A1 (fr) * 2012-02-07 2013-08-15 Annikki Gmbh Procédé de production de dérivés de furane à partir de glucose
WO2014154676A1 (fr) * 2013-03-27 2014-10-02 Annikki Gmbh Procédé servant à isomériser du glucose
EP2812439B1 (fr) * 2012-02-07 2019-05-22 Annikki GmbH Procédé destiné à la régénération enzymatique de co-facteurs redox

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19963126A1 (de) 1999-12-24 2001-07-12 Suedzucker Ag Verfahren zur Herstellung von 6-O-alpha-D-Glucopyranosyl-D-sorbit
FR2820973B1 (fr) * 2001-02-19 2003-05-23 Oreal Composition comportant de la vitamine c preparee durant l'application, utilisation d'enzymes pour la formation de vitamine c a usage topique et procede de traitement cosmetique
KR101031451B1 (ko) * 2002-09-27 2011-04-26 디에스엠 아이피 어셋츠 비.브이. 비타민 ｃ의 생성 방법

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2317310A1 (fr) * 1975-07-10 1977-02-04 Snam Progetti Procede permettant d'ameliorer l'activite d'enzymes oxyreductases noyes dans une structure filamentaire

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2317310A1 (fr) * 1975-07-10 1977-02-04 Snam Progetti Procede permettant d'ameliorer l'activite d'enzymes oxyreductases noyes dans une structure filamentaire

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chemiker Zeitung, Vol. 108, No. 5, 1984, E. BURGER et al.: "Herstellung Organischer Verbindungen mittels Enzymen", see page 162, column 1, last paragraph - column 2, first paragraph; figure 7C *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997029194A3 (fr) * 1996-02-09 1997-10-02 Herbstreith & Fox Kg Pektin Fa Preparation d'acide l-ascorbique
WO2013117585A1 (fr) * 2012-02-07 2013-08-15 Annikki Gmbh Procédé de production de dérivés de furane à partir de glucose
US9902981B2 (en) 2012-02-07 2018-02-27 Annikki Gmbh Process for the production of furan derivatives from glucose
EP2812439B1 (fr) * 2012-02-07 2019-05-22 Annikki GmbH Procédé destiné à la régénération enzymatique de co-facteurs redox
US11339415B2 (en) 2012-02-07 2022-05-24 Annikki Gmbh Process for the enzymatic regeneration of redox cofactors
WO2014154676A1 (fr) * 2013-03-27 2014-10-02 Annikki Gmbh Procédé servant à isomériser du glucose
CN105102626A (zh) * 2013-03-27 2015-11-25 安尼基有限责任公司 葡萄糖异构化的方法
CN105102626B (zh) * 2013-03-27 2019-01-01 安尼基有限责任公司 葡萄糖异构化的方法
US10253340B2 (en) 2013-03-27 2019-04-09 Annikki Gmbh Method for the isomerisation of glucose

Also Published As

Publication number Publication date
DE3502141C2 (fr) 1991-08-29
EP0209583A1 (fr) 1987-01-28
JPS62501747A (ja) 1987-07-16
DE3502141A1 (de) 1986-10-16

Similar Documents

Publication Publication Date Title
EP0008031B1 (fr) Procédé de préparation de 6-amino-6-désoxy-L-sorbose
DE3882655T2 (de) Verfahren zur Herstellung von L-Rhamnose.
DE3823864A1 (de) Enymatisches verfahren zur herstellung von optisch aktiven cyanhydrinen
DE2343587A1 (de) Verfahren zur herstellung von 2-ketol-gulonsaeure
DE602004008875T2 (de) Herstellung von milchsäure aus einem pentose-enthaltenden substrat
EP0132557B1 (fr) Procédé de préparation enzymatique en continu de l'acide gluconique ou de ses dérivés ou de sorbitol et/ou de mannitol
DE3502141C2 (fr)
US3959076A (en) Process for producing 2-keto-L-gulonic acid
EP0347374B1 (fr) Procédé de préparation d'acides hydroxylés
US3963574A (en) Process for producing 2-keto-L-gulonic acid
JPH11266888A (ja) キシリトールの製造法
AU736422B2 (en) Method for producing an oxide with a fermentation process
DE4227076A1 (de) Verfahren zur Herstellung substituierter Methoxyphenole und dafür geeignete Mikroorganismen
DE60004763T2 (de) Verfahren zur Herstellung von (s)-3-Halogeno-1,2-propandiol durch Pseudomonas
DE4444404A1 (de) Mikrobielles Verfahren zur Herstellung von Dihydroxyaceton unter Rückführung von Biomasse
DE19928158C2 (de) Verfahren zur Herstellung von aromatischen Carbonylverbindungen aus Styrolen
DE69614760T2 (de) Optische Trennung von Chlorhydrin mittles Mikroorganismen
DE4024937C1 (en) Microbial fermentation using continuously regenerated redox mediator - where microbe is anaerobic,facultative anaerobe, or is micro-aerophilic or aero:tolerant
EP4656731A1 (fr) Procédé de préparation d'acide galactarique
WO2025248071A2 (fr) Procédé de production d'acide galactarique
EP0683820A1 (fr) Procede enzymatique pour fabriquer du dihydroxyacetone phosphate a partir de glycerophosphate et son utilisation en additions aldoliques enzymatiques
KR950009832B1 (ko) 지모모나스 모빌리스 sg11을 이용한 글루코산 및 글루시톨의 제조방법
DD153131A5 (de) Verfahren zur herstellung von 2,5-diketogluconsaeure
EP4488376A1 (fr) Procédé de préparation d'une solution aqueuse contenant du l-sorbose
EP0114630A2 (fr) Mycélium de moisissures perméabilisé ayant un système glucose oxidase-catalase immobilisé intact, sa préparation et son application

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE FR GB IT LU NL SE

WWE Wipo information: entry into national phase

Ref document number: 1986901053

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1986901053

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1986901053

Country of ref document: EP