CA1119981A - Process for preparing 2,5-diketogluconic acid - Google Patents
Process for preparing 2,5-diketogluconic acidInfo
- Publication number
- CA1119981A CA1119981A CA000316362A CA316362A CA1119981A CA 1119981 A CA1119981 A CA 1119981A CA 000316362 A CA000316362 A CA 000316362A CA 316362 A CA316362 A CA 316362A CA 1119981 A CA1119981 A CA 1119981A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- diketogluconic
- glucose
- diketogluconic acid
- medium
- 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
- RXMWXENJQAINCC-DMTCNVIQSA-N 2,5-didehydro-D-gluconic acid Chemical compound OCC(=O)[C@@H](O)[C@H](O)C(=O)C(O)=O RXMWXENJQAINCC-DMTCNVIQSA-N 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 241000589220 Acetobacter Species 0.000 claims abstract description 14
- 238000000855 fermentation Methods 0.000 claims abstract description 13
- 230000004151 fermentation Effects 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 9
- 230000001902 propagating effect Effects 0.000 claims abstract description 3
- 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 claims description 15
- 239000008103 glucose Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 abstract description 5
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000006481 glucose medium Substances 0.000 abstract 1
- 239000002609 medium Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VBUYCZFBVCCYFD-JJYYJPOSSA-N 2-dehydro-D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-JJYYJPOSSA-N 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 241000209149 Zea Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 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
- 239000001058 brown pigment Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 235000010350 erythorbic acid Nutrition 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 150000004715 keto acids Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241001600170 Fragum Species 0.000 description 1
- 241001621835 Frateuria aurantia Species 0.000 description 1
- 241000032681 Gluconacetobacter Species 0.000 description 1
- 241000032686 Gluconacetobacter liquefaciens Species 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000013587 production medium Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Process for preparing 2,5-Diketogluconic Acid ABSTRACT
A process for producing 2,5-diketogluconic acid which comprises aerobically propagating Acetobacter cerinus in a glucose medium and then recovering the resulting 2,5-diketogluconic acid or processing the fermentation broth by selective reduction to yield 2-ketogulonic and 2-ketogluconic acids.
A process for producing 2,5-diketogluconic acid which comprises aerobically propagating Acetobacter cerinus in a glucose medium and then recovering the resulting 2,5-diketogluconic acid or processing the fermentation broth by selective reduction to yield 2-ketogulonic and 2-ketogluconic acids.
Description
This invention relates -to the preparation of 2,5-diketo-gluconic acid.
2,5-Diketogluconic acid is a useful intermediate in the synthesis of vitamin C. Heretofore, 2,5-diketoyluconic acid has been produced by several different varie-ties of bacteria such as A etobacter melanogenum, Acetobacter aurantium, Gluconoacetobacter rubiginosus, Gluconoacetobacter liquifaciens and Pseudomonas ses-aml. The use of these microorganisms, however, is not completely desirable from an industrial point of view because of the pro-duction of large amounts of brown or yellowish-brown pigments as by-products of cultivation, thereby decreasing the purity of the co-produced 2,5-diketogluconic acid.
U.S. Patent 3,790,444 claims the production of 2,5-diketo-gluconic acid~ without accompanying brown pigment, by a new species designated Acetobacter fragum.
This invention is concerned with an economical process for preparing 2,5-diketogluconic acid by the use of readily available, publicly held strains of Acetobacter cerlnus. Two of these strains, I~O 3263 and 3266, produce 2,5-diketogluconic acid in yields of >95~ (based on glucose). The inven-tion accordingly provides a process for producing 2,5-diketogluconic acid which comprises aerobically propagating Acetobac-ter cerinus in a fer-mentation medium in which glucose is the main carbon source.
2,5-Diketogluconic acid is useful as an in-termedia-te Eor the preparation of ascorbic acid. An aclueous solution of 2,5-diketogluconic acid may be selectively reduced to provide a mixture of 2-ketogulonate and 2-ketogluconate which can be con-verted to ascorbic and erythorbic acids.
2,5-Diketogluconic acid is readily prepared by bacterial action on glucose employing according to the process of the present invention, readily available strains of A tobacter cerinus. All of the listed publicly held strains of Acetobacter cerinus have been tested and shown in this inves-tigation to produce keto-acids at a yield of 50-95% (based on glucose). When - 2a -~' Acetobacter cerinus IFO 3263 or 3266 is employed, the keto acid produced is entirely desired 2,5-diketogluconic acid in yields of > 95% (based on glucose). The available, publicly held strains of Acetobacter cerinus are as follows:
. _ IFO 3262 (ATCC 12303) These strains of Acetobacter cerinus are cultured in a medium of which the main carbon source is glucose. These micro-organisms do not require expensive organic nitrogen sources such ; as peptone or meat extract. When urea and inorganic nitrogen sources such as ammonium sulfate, ammonium nitrate or ammonium phosphate are employed, nicotinic acid is added as an essential growth factor.
The ylucose concentration in the medium varies betweeen 2.5 and 20%, preferably between 10 and 12%, in order to obtain 2,5-diketogluconic acid most economically. The fermentation tempera-ture is between 20 and 35C., preferably between 25 and 30C., most preferably around 28C. The initial pH of the culture medium may range from 3.5 to 7.5, preferably at 5 to 6. During the course of the ermentation, the pH is maintained at about 5.5 by the addition of sodium hydroxide solution. Calcium carbonate may be used for pH control and is added in medium make-up af-ter autoclaving at an amount of 30 grams per 110 grams of glucose.
After inoculation, the fermentation medium is agitated with a mechanical stirrer at about 1700 r.p.m., and aerated at the rate of 0.5 to 1 volume of air per volume of broth per minutes.
Employing Acetobacter cerinus IFO 3263 or 3266, the fermen-tation is conducted until a yield of 2,5-diketogluconic acid of at least 90% (based on glucose) is obtained (36-40 hours).
8~L
It was determined by paper chromatography that the c~nversion of glucose to 2,5-diketogluconic is via the following pathways:
glucose-~ 2-ketogluconic acid-~2,5-diketogluconic acid glucose-~ S-ketogluconic acid-~2,5-diketogluconic acid S Whatman No. 1 and No. 4 paper are used employing a solvent system of methylethyl ketone:acetone:formic acid:water (80:6:2:12). The acid spots are located by spraying with a 0.2~ o-phenylenediamine ethano1ic solution containing 1% nitric acid and heat1ng to about 70C, ~5-ketsgluconic acid - blue; 2-keto-gluconic acid - yellow;
2,5-diketogluconic acid - green). High pxessure liquid chromato-graphy may also be used for identification.
2,5 Diketogluconic acid may be separated and recovered from the final fermentation broth by any conventional procedure known to those skilled in the art. The filtered fermentation broth may be processed as is by treatment with a bo.rohydride and the resul-tant mixture of 2-ketogluconic acid and 2-ketogulonic acid hydrclyzed to yield ascorbic and erythorbic acids.
The following aqueous inoculum medium was prepared:
Grams/liter Glucose 25 Corn steep liquor 5 KH2PO4 0.5 K2HPO4 0.5 MgSO4 7H2O 0.2 CaCO3 6.3 pH 6.2 A shake flask containing one liter of medium was autoclaved for 30 minutes at 121C. The pH of the cooled medium was 5.0, Cells of Acetobacter cerinus IFO 3263 from a nutrient agar slant (5 ml of a 20 ml sterile aqueous suspension) were added to the flask which was then shaken on a rotary shaker at about 28~C. for about 24 hours.
An aliquot of the culture growth sufficient to provide a 5%, v/v inoculum was added to a 4-liter stirred fermentor contain-ing 2 liters of the following production medium:
In~redient Grams/liter Glucose 110 Corn steep liquor 0.5 (NH4~2HPO4 0.58 K~l2PO4 1.5 MgSO4 7H2O 0.5 Urea 0.5 cuSo4'5H2 1 mg Nicotinic acid 300 pH 6.0 The fermentation was conducted at a temperature of about 28C. with stirring at 1700 r.p.m. and aeration at the rate of 0.75 volume per volume of broth per minutes. After a fermenta-tion period of about 20 hours, sterile glucose was added (55 grams/liter). The pH was maintained at 5.5 by the addition of sodium hydroxide solution. The fermentation was continued until a yield of 2,5-diketogluconic acid of > 95% (based on glucose) was obtained.
The method of Example 1 may be repeated with comparable re-sults employing Acetobacter cerinus IFO 3266.
U.S. Patent 3,790,444 claims the production of 2,5-diketo-gluconic acid~ without accompanying brown pigment, by a new species designated Acetobacter fragum.
This invention is concerned with an economical process for preparing 2,5-diketogluconic acid by the use of readily available, publicly held strains of Acetobacter cerlnus. Two of these strains, I~O 3263 and 3266, produce 2,5-diketogluconic acid in yields of >95~ (based on glucose). The inven-tion accordingly provides a process for producing 2,5-diketogluconic acid which comprises aerobically propagating Acetobac-ter cerinus in a fer-mentation medium in which glucose is the main carbon source.
2,5-Diketogluconic acid is useful as an in-termedia-te Eor the preparation of ascorbic acid. An aclueous solution of 2,5-diketogluconic acid may be selectively reduced to provide a mixture of 2-ketogulonate and 2-ketogluconate which can be con-verted to ascorbic and erythorbic acids.
2,5-Diketogluconic acid is readily prepared by bacterial action on glucose employing according to the process of the present invention, readily available strains of A tobacter cerinus. All of the listed publicly held strains of Acetobacter cerinus have been tested and shown in this inves-tigation to produce keto-acids at a yield of 50-95% (based on glucose). When - 2a -~' Acetobacter cerinus IFO 3263 or 3266 is employed, the keto acid produced is entirely desired 2,5-diketogluconic acid in yields of > 95% (based on glucose). The available, publicly held strains of Acetobacter cerinus are as follows:
. _ IFO 3262 (ATCC 12303) These strains of Acetobacter cerinus are cultured in a medium of which the main carbon source is glucose. These micro-organisms do not require expensive organic nitrogen sources such ; as peptone or meat extract. When urea and inorganic nitrogen sources such as ammonium sulfate, ammonium nitrate or ammonium phosphate are employed, nicotinic acid is added as an essential growth factor.
The ylucose concentration in the medium varies betweeen 2.5 and 20%, preferably between 10 and 12%, in order to obtain 2,5-diketogluconic acid most economically. The fermentation tempera-ture is between 20 and 35C., preferably between 25 and 30C., most preferably around 28C. The initial pH of the culture medium may range from 3.5 to 7.5, preferably at 5 to 6. During the course of the ermentation, the pH is maintained at about 5.5 by the addition of sodium hydroxide solution. Calcium carbonate may be used for pH control and is added in medium make-up af-ter autoclaving at an amount of 30 grams per 110 grams of glucose.
After inoculation, the fermentation medium is agitated with a mechanical stirrer at about 1700 r.p.m., and aerated at the rate of 0.5 to 1 volume of air per volume of broth per minutes.
Employing Acetobacter cerinus IFO 3263 or 3266, the fermen-tation is conducted until a yield of 2,5-diketogluconic acid of at least 90% (based on glucose) is obtained (36-40 hours).
8~L
It was determined by paper chromatography that the c~nversion of glucose to 2,5-diketogluconic is via the following pathways:
glucose-~ 2-ketogluconic acid-~2,5-diketogluconic acid glucose-~ S-ketogluconic acid-~2,5-diketogluconic acid S Whatman No. 1 and No. 4 paper are used employing a solvent system of methylethyl ketone:acetone:formic acid:water (80:6:2:12). The acid spots are located by spraying with a 0.2~ o-phenylenediamine ethano1ic solution containing 1% nitric acid and heat1ng to about 70C, ~5-ketsgluconic acid - blue; 2-keto-gluconic acid - yellow;
2,5-diketogluconic acid - green). High pxessure liquid chromato-graphy may also be used for identification.
2,5 Diketogluconic acid may be separated and recovered from the final fermentation broth by any conventional procedure known to those skilled in the art. The filtered fermentation broth may be processed as is by treatment with a bo.rohydride and the resul-tant mixture of 2-ketogluconic acid and 2-ketogulonic acid hydrclyzed to yield ascorbic and erythorbic acids.
The following aqueous inoculum medium was prepared:
Grams/liter Glucose 25 Corn steep liquor 5 KH2PO4 0.5 K2HPO4 0.5 MgSO4 7H2O 0.2 CaCO3 6.3 pH 6.2 A shake flask containing one liter of medium was autoclaved for 30 minutes at 121C. The pH of the cooled medium was 5.0, Cells of Acetobacter cerinus IFO 3263 from a nutrient agar slant (5 ml of a 20 ml sterile aqueous suspension) were added to the flask which was then shaken on a rotary shaker at about 28~C. for about 24 hours.
An aliquot of the culture growth sufficient to provide a 5%, v/v inoculum was added to a 4-liter stirred fermentor contain-ing 2 liters of the following production medium:
In~redient Grams/liter Glucose 110 Corn steep liquor 0.5 (NH4~2HPO4 0.58 K~l2PO4 1.5 MgSO4 7H2O 0.5 Urea 0.5 cuSo4'5H2 1 mg Nicotinic acid 300 pH 6.0 The fermentation was conducted at a temperature of about 28C. with stirring at 1700 r.p.m. and aeration at the rate of 0.75 volume per volume of broth per minutes. After a fermenta-tion period of about 20 hours, sterile glucose was added (55 grams/liter). The pH was maintained at 5.5 by the addition of sodium hydroxide solution. The fermentation was continued until a yield of 2,5-diketogluconic acid of > 95% (based on glucose) was obtained.
The method of Example 1 may be repeated with comparable re-sults employing Acetobacter cerinus IFO 3266.
Claims (4)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for producing 2,5-diketogluconic acid which comprises aerobically propagating Acetobacter cerinus in a fer-mentation medium in which glucose is the main carbon source.
2. A process as claimed in claim 1, wherein the glucose concentration in the medium is from 2.5 to 20%, the fermentation temperature is from 20 to 35°C, the initial pH is from 3.5 and 7.5, and the pH during the course of the fermentation is main-tained at about 5.5.
3. A process as claimed in claim 1 or 2 wherein said Acetobacter cerinus is strain IFO 3263.
4. A process as claimed in claim 1 or 2 wherein said Acetobacter cerinus is strain IFO 3266.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85295077A | 1977-11-18 | 1977-11-18 | |
| US852,950 | 1977-11-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1119981A true CA1119981A (en) | 1982-03-16 |
Family
ID=25314629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000316362A Expired CA1119981A (en) | 1977-11-18 | 1978-11-16 | Process for preparing 2,5-diketogluconic acid |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS54145283A (en) |
| AR (1) | AR218348A1 (en) |
| AT (1) | AT363887B (en) |
| AU (1) | AU505434B1 (en) |
| BE (1) | BE872095A (en) |
| BR (1) | BR7807524A (en) |
| CA (1) | CA1119981A (en) |
| CH (1) | CH643592A5 (en) |
| DD (1) | DD140459A5 (en) |
| DE (1) | DE2849393C2 (en) |
| DK (1) | DK152679C (en) |
| ES (1) | ES475216A1 (en) |
| FI (1) | FI782871A (en) |
| FR (1) | FR2409304A1 (en) |
| GB (1) | GB2008116B (en) |
| HU (1) | HU175521B (en) |
| IL (1) | IL55969A0 (en) |
| IT (1) | IT1101715B (en) |
| LU (1) | LU80536A1 (en) |
| NL (1) | NL7811353A (en) |
| NO (1) | NO783877L (en) |
| PL (1) | PL118433B1 (en) |
| PT (1) | PT68789A (en) |
| RO (1) | RO75389A (en) |
| SE (1) | SE7809345L (en) |
| ZA (1) | ZA786487B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4316960A (en) * | 1979-09-28 | 1982-02-23 | Pfizer Inc. | Preparation of 2,5-diketogluconic acid |
| JPS6365970A (en) * | 1987-08-25 | 1988-03-24 | Kyushu Hitachi Maxell Ltd | electric sprayer |
| FR2820973B1 (en) | 2001-02-19 | 2003-05-23 | Oreal | COMPOSITION COMPRISING VITAMIN C PREPARED DURING APPLICATION, USE OF ENZYMES FOR THE FORMATION OF VITAMIN C FOR TOPICAL USE AND COSMETIC PROCESSING METHOD |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3234105A (en) * | 1962-09-20 | 1966-02-08 | Takeda Chemical Industries Ltd | Method for producing 2-keto-lgulonic acid |
| US3790444A (en) * | 1971-03-09 | 1974-02-05 | Daiichi Seiyaku Co | Process for preparing diketogluconic acid |
| JPS5135485A (en) * | 1974-09-20 | 1976-03-25 | Shionogi Seiyaku Kk | 22 keto ll guronsan no seizohoho |
-
1978
- 1978-09-05 SE SE7809345A patent/SE7809345L/en unknown
- 1978-09-13 AU AU39819/78A patent/AU505434B1/en not_active Expired
- 1978-09-20 FI FI782871A patent/FI782871A/en not_active IP Right Cessation
- 1978-10-31 CH CH1121978A patent/CH643592A5/en not_active IP Right Cessation
- 1978-11-02 HU HU78PI647A patent/HU175521B/en unknown
- 1978-11-03 PL PL1978210683A patent/PL118433B1/en unknown
- 1978-11-03 DD DD78208866A patent/DD140459A5/en unknown
- 1978-11-03 RO RO7895585A patent/RO75389A/en unknown
- 1978-11-14 DE DE2849393A patent/DE2849393C2/en not_active Expired
- 1978-11-15 PT PT68789A patent/PT68789A/en unknown
- 1978-11-16 GB GB7844723A patent/GB2008116B/en not_active Expired
- 1978-11-16 IT IT29866/78A patent/IT1101715B/en active
- 1978-11-16 LU LU80536A patent/LU80536A1/en unknown
- 1978-11-16 CA CA000316362A patent/CA1119981A/en not_active Expired
- 1978-11-16 BR BR7807524A patent/BR7807524A/en unknown
- 1978-11-17 AR AR274472A patent/AR218348A1/en active
- 1978-11-17 FR FR7832491A patent/FR2409304A1/en not_active Withdrawn
- 1978-11-17 IL IL55969A patent/IL55969A0/en unknown
- 1978-11-17 NO NO783877A patent/NO783877L/en unknown
- 1978-11-17 ZA ZA00786487A patent/ZA786487B/en unknown
- 1978-11-17 DK DK512978A patent/DK152679C/en active
- 1978-11-17 AT AT0823178A patent/AT363887B/en not_active IP Right Cessation
- 1978-11-17 ES ES475216A patent/ES475216A1/en not_active Expired
- 1978-11-17 JP JP14215078A patent/JPS54145283A/en active Granted
- 1978-11-17 NL NL7811353A patent/NL7811353A/en not_active Application Discontinuation
- 1978-11-17 BE BE191792A patent/BE872095A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK152679C (en) | 1988-08-22 |
| ES475216A1 (en) | 1979-04-16 |
| JPS54145283A (en) | 1979-11-13 |
| DK152679B (en) | 1988-04-11 |
| RO75389A (en) | 1980-11-30 |
| ATA823178A (en) | 1981-02-15 |
| PT68789A (en) | 1978-12-01 |
| AT363887B (en) | 1981-09-10 |
| SE7809345L (en) | 1979-05-19 |
| GB2008116A (en) | 1979-05-31 |
| NL7811353A (en) | 1979-05-22 |
| BE872095A (en) | 1979-05-17 |
| PL210683A1 (en) | 1979-06-18 |
| DE2849393A1 (en) | 1979-05-23 |
| FR2409304A1 (en) | 1979-06-15 |
| IT7829866A0 (en) | 1978-11-16 |
| DK512978A (en) | 1979-05-19 |
| IL55969A0 (en) | 1979-01-31 |
| AU505434B1 (en) | 1979-11-22 |
| CH643592A5 (en) | 1984-06-15 |
| LU80536A1 (en) | 1980-06-05 |
| GB2008116B (en) | 1982-03-17 |
| FI782871A (en) | 1979-05-19 |
| IT1101715B (en) | 1985-10-07 |
| ZA786487B (en) | 1979-10-31 |
| DE2849393C2 (en) | 1983-05-05 |
| PL118433B1 (en) | 1981-10-31 |
| AR218348A1 (en) | 1980-05-30 |
| JPS579357B2 (en) | 1982-02-20 |
| HU175521B (en) | 1980-08-28 |
| BR7807524A (en) | 1979-07-24 |
| NO783877L (en) | 1979-05-21 |
| DD140459A5 (en) | 1980-03-05 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |