DE887933C - Process for the preparation of 2-keto-h-idonic acid - Google Patents
Process for the preparation of 2-keto-h-idonic acidInfo
- Publication number
- DE887933C DE887933C DEK11377A DEK0011377A DE887933C DE 887933 C DE887933 C DE 887933C DE K11377 A DEK11377 A DE K11377A DE K0011377 A DEK0011377 A DE K0011377A DE 887933 C DE887933 C DE 887933C
- Authority
- DE
- Germany
- Prior art keywords
- idonic acid
- keto
- fermentation
- preparation
- acid
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000000855 fermentation Methods 0.000 claims description 16
- 230000004151 fermentation Effects 0.000 claims description 16
- 244000005700 microbiome Species 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 241000589232 Gluconobacter oxydans Species 0.000 claims description 3
- 241000589516 Pseudomonas Species 0.000 claims description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 3
- 238000009423 ventilation Methods 0.000 claims description 2
- RGHNJXZEOKUKBD-SKNVOMKLSA-N L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SKNVOMKLSA-N 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 229910052791 calcium Inorganic materials 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000589540 Pseudomonas fluorescens Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
- C07H7/027—Keto-aldonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/62—Three oxygen atoms, e.g. ascorbic acid
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Verfahren zur Herstellung von 2-Keto-h-idonsäure Es wurde schon vorgeschlagen, 2-Keto-h-idonsäure durch Vergärung von l,i-Idonsäure bzw. deren Salzen mittels Pseudomonas Mildenbergii bzw. Cyanococus chromospirans als Gärungserreger herzustellen. Diese Mikroorganismen sind nur schwierig oder durch Zufall zugänglich.Process for the preparation of 2-keto-h-idonic acid It has already been proposed 2-Keto-h-idonic acid by fermentation of l, i-idonic acid or its salts by means of Pseudomonas Mildenbergii or Cyanococus chromospirans as fermentation pathogens. These Microorganisms are difficult or accidentally accessible.
Es wurde nun gefunden, daB sich diese Vergärung auch mit anderen leicht erhältlichen Bakterienarten der Pseudomonasgruppe, wie Pseudomonas aeruginosa und Pseudomonas fluorescens, sowie auch mit Acetobacter suboxydans melanogenum durchführen läBt. Diese Mikroorganismen lassen sich durch geeignete Passagenzüchtung an die h-Idonsäure so weit assimilieren, daB der Gäreffekt demjenigen der bereits verwendeten Mikroorganismen gleichkommt. Es hat sich ferner gezeigt, daB die mit den genannten Bakterien beim gewöhnlichen Züchtungsversuch auftretende Farbstoffbildung bei der Vergärung der- h-Idonsäure ausbleibt, so daB nahezu farblose Gärlösungen erhalten werden. Für die Vergärung kann das Calcium-, Kalium- oder Ammoniumsalz der h-Idonsäure in Konzentrationen bis zu io °/o angewandt werden; die Vergärung wird zweckmäßig unter Belüftung bei Temperaturen von 28 bis 30° durchgeführt. Beispiele i. 50 g Calcium=h-idonat werden in 11 i°/oigem Hefeextrakt oder Hefeautolysat gelöst, 5 g d-Glucose zugesetzt, sterilisiert und mit 50 ccm einer durch Passagenzüchtung auf dem gleichen Nährboden aktivierten Kultur von Pseudomonas fluorescens beimpft. Nach einer Gärdauer von 3 bis 5 Tagen bei gleichzeitiger Belüftung reit steriler Luft oder Sauerstoff und einer Gärtemperatur von 28 bis 30° ist das Maximum der Gärung erreicht. Nach Filtration der Bakterien wird im Vakuum bei 40° zu einem Sirup eingeengt und dieser in 11 Methanol eingerührt. Das in Flocken ausfallende Calcium-2-keto=h-idonat wird filtriert und im Vakuum getrocknet. Ausbeute: 35 bis 40 g Calcium-2-keto-h-idonat = 7o bis 8o °/o der Theorie.It has now been found that this fermentation can also be carried out with other easily obtainable types of bacteria of the Pseudomonas group, such as Pseudomonas aeruginosa and Pseudomonas fluorescens, as well as with Acetobacter suboxydans melanogenum. These microorganisms can be assimilated to the h-idonic acid by suitable passage cultivation to such an extent that the fermentation effect is equal to that of the microorganisms already used. It has also been shown that the dye formation that occurs with the bacteria mentioned in the usual cultivation experiment does not occur during fermentation of the ε-idonic acid, so that almost colorless fermentation solutions are obtained. The calcium, potassium or ammonium salt of h-idonic acid can be used in concentrations of up to 10% for the fermentation; the fermentation is expediently carried out with aeration at temperatures of 28 to 30 °. Examples i. 50 g Calcium = h-idonate are dissolved in 1 1 i ° / pc alcohol yeast extract or yeast autolysate, 5 g of D-glucose was added, and sterilized with 50 cc of activated by culturing passages on the same nutrient medium culture of Pseudomonas fluorescens inoculated. After a fermentation period of 3 to 5 days with simultaneous ventilation with sterile air or oxygen and a fermentation temperature of 28 to 30 °, the maximum fermentation is reached. After filtration, the bacteria is concentrated at 40 ° to a syrup and this was stirred into 1 1 of methanol in vacuo. The calcium 2-keto = h-idonate which precipitates out in flakes is filtered and dried in vacuo. Yield: 35 to 40 g calcium 2-keto-h-idonate = 70 to 80% of theory.
2. ioo g Calcium-h=idonat werden in i 1 i°/oigem Hefeautolysat unter Zusatz von 5 g d-Glucose, 2 g (N H4)2HP04, i g K H?, P04 und 0,25 g Mg S0V7H20 gelöst und nach der Sterilisation mit ioo ccm einer durch Passagenzüchtung auf dem gleichen Nährboden erhaltenen Kultur von Pseudomonas aeruginosa beimpft. Das Maximum der Gärung wird bei Belüftung mit Luft oder Sauerstoff nach 4 bis 6 Tagen erreicht. Man fällt das Calcium mit einer äquivalenten Menge Oxalsäure oder verdünnter Schwefelsäure aus, filtriert ab und gewinnt nach dem Einengen im Vakuum 6o bis 7o °/o der Theorie kristallisierte 2-Keto-lY-idonsäure.2. 100 g calcium h = idonate are dissolved in i 1% yeast autolysate with the addition of 5 g d-glucose, 2 g (N H4) 2HP04, ig KH ?, PO4 and 0.25 g Mg S0V7H20 and after sterilization with 100 cc of a culture of Pseudomonas aeruginosa obtained by passage cultivation on the same nutrient medium. The maximum fermentation is reached after 4 to 6 days with aeration with air or oxygen. The calcium is precipitated with an equivalent amount of oxalic acid or dilute sulfuric acid, filtered off and, after concentration in vacuo, 60 to 70% of theory crystallized 2-keto-lY-idonic acid is obtained.
3. 50 g Calcium-i#=idonat werden in z 1 i°/oigem Hefeextrakt gelöst, 5 9 d-Glucose zugesetzt, sterilisiert und mit 50 ccm einer durch Passagenzüchtung aktivierten Kultur von Acetobacter suboxydans melanogenum beimpft. Nach einer Gärdauer von 4 bis 8 Tagen gewinnt man nach Aufarbeitung der Gärlösung gemäß Beispiel i bzw. 2 6o bis 8o °/o Calciumz-keto-h-idonat bzw. 2-Keto ,h-idonsäure.3. 50 g of calcium idonate i # = 1 i z dissolved in ° / pc alcohol yeast extract, 5 9 d-glucose was added, and sterilized with 50 cc of an activated passages breeding culture of Acetobacter suboxydans melanogenum inoculated. After a fermentation period of 4 to 8 days, after working up the fermentation solution according to Example 1 or 2, 6o to 80% calcium z-keto-h-idonate or 2-keto, h-idonic acid is obtained.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK11377A DE887933C (en) | 1951-09-22 | 1951-09-22 | Process for the preparation of 2-keto-h-idonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK11377A DE887933C (en) | 1951-09-22 | 1951-09-22 | Process for the preparation of 2-keto-h-idonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE887933C true DE887933C (en) | 1953-08-27 |
Family
ID=7213300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK11377A Expired DE887933C (en) | 1951-09-22 | 1951-09-22 | Process for the preparation of 2-keto-h-idonic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE887933C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1009583B (en) * | 1954-08-10 | 1957-06-06 | Pfizer & Co C | Process for the biochemical production of 2-keto-1-gulonic acid |
| DE1018827B (en) * | 1954-04-26 | 1957-11-07 | Pfizer & Co C | Process for the biotechnological production of 2-keto-1-gulonic acid |
-
1951
- 1951-09-22 DE DEK11377A patent/DE887933C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1018827B (en) * | 1954-04-26 | 1957-11-07 | Pfizer & Co C | Process for the biotechnological production of 2-keto-1-gulonic acid |
| DE1009583B (en) * | 1954-08-10 | 1957-06-06 | Pfizer & Co C | Process for the biochemical production of 2-keto-1-gulonic acid |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1812710C3 (en) | Process for the biotechnical production of citric acid and its salts by microorganisms | |
| DE887933C (en) | Process for the preparation of 2-keto-h-idonic acid | |
| DE283882C (en) | ||
| DE3020851C2 (en) | Adenosine 5'-triphosphate | |
| DE2202701C3 (en) | Process for the biotechnological production of citric acid | |
| AT224265B (en) | Process for the production of Laevansucrase | |
| DE1009583B (en) | Process for the biochemical production of 2-keto-1-gulonic acid | |
| DE696578C (en) | Process for the production of an organic nitrogen feed as an additive to water | |
| CH309768A (en) | Process for the preparation of 2-keto-l-idonic acid. | |
| DE2366505C2 (en) | Use of the strain Pseudomonas ATCC 21973 for the in situ production of an aminotransferase | |
| DE664428C (en) | Process for the production of tanning extracts from sulphite cellulose waste liquor | |
| AT127373B (en) | Process for the production of gluconic acid salts by fermentation. | |
| AT205666B (en) | Process for the preparation of ribosides of nucleic acid bases and their analogues | |
| AT220292B (en) | Process for the production of vitamins of the B12 group by propionic acid bacteria | |
| DE1642716A1 (en) | Process for the production of citric acid | |
| DE931495C (en) | Making an antibiotic | |
| AT233737B (en) | Process for the production of an antibiotic from propionic acid bacteria | |
| DE1091705B (en) | Process for the production of vitamins of the B group by propionic acid bacteria | |
| AT205169B (en) | Process for obtaining tyrothricin and vitamin B12 | |
| DE556731C (en) | Process for the production of glycic acid | |
| DE1149857B (en) | Process for the preparation of an agent effective against diseases of the oral cavity | |
| DE880786C (en) | Process for the manufacture of an antibiotic | |
| AT143292B (en) | Process for the production of permanent permanent cultures of acid-forming bacteria, in particular lactic acid bacteria. | |
| AT204178B (en) | Process for the biosynthetic production of vitamins of the B12 group | |
| DE1050721B (en) | Process for the production of kojic acid |