US3296087A - Process for preparing 5'-nucleotides - Google Patents

Process for preparing 5'-nucleotides Download PDF

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Publication number
US3296087A
US3296087A US399082A US39908264A US3296087A US 3296087 A US3296087 A US 3296087A US 399082 A US399082 A US 399082A US 39908264 A US39908264 A US 39908264A US 3296087 A US3296087 A US 3296087A
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acid
nucleotide
atcc
prepared
purine
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US399082A
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Mitsugi Koji
Kamimura Akira
Okumura Shinji
Katsuya Noboru
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Ajinomoto Co Inc
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Ajinomoto Co Inc
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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
    • C12P19/26—Preparation of nitrogen-containing carbohydrates
    • C12P19/28—N-glycosides
    • C12P19/30—Nucleotides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/02—Phosphorylation
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/828—Aerobacter
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/829—Alcaligenes
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/848—Escherichia
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/848—Escherichia
    • Y10S435/849—Escherichia coli
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/859—Micrococcus
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/873—Proteus

Definitions

  • the present invention relates to a process for preparing 5'-nucleotides, more particularly to a biochemical synthesis of 5-nucleotides.
  • Such 5'-ribonucleotides as 5-inosinic acid, 5'-guanylic acid or 5'-Xanthylic acid are known to be useful as flavoring agents and also to possess useful pharmacological properties.
  • Other nucleotides, such as 5'-adenylic acid, 5'- uridylic acid, and 5'-deoxyadenylic acid are of interest to pharmacologists and biochemists.
  • microorganisms which can be used in the present invention belong to many genera of bacteria. Suitable strains have been isolated from bacteria of the genera Pseudomonas, Alcaligenes, Serratia, Flavobacterium, Micrococcus, Staphylococcus, Proteus, Aerobacter and Escherichia. The following test has been employed for screening the bacteria.
  • Strains to be tested were cultured in a suitable conventional nutrient medium, and a suspension of living bacterial cells was prepared.
  • the suspension containing 0.1-0.5 g. of cells, on a dry basis, was added to 100 ml. of a solution containing 0.135 'g. adenine and 1.43 g. disodium-5'-uridylate.
  • the mixture was incubated without agitation at 40 C. for 3-20 hours While being kept mildly alkaline (pH 89), and the amount of 5'-adenylic acid formed was determined in a conventional manner by paper electro-phoresis in 10% acetic acid solution.
  • Some 5'-inosinic acid may be formed by deamination of an amino group at the 6-position of 5-adenylic acid.
  • Table 1 shows the results of screening tests performed with various strains of bacteria.
  • Agrobacterium tumefaciens ATCC-4720 0 0 Agrobacterium radiobacter (ATC (3-6466) 0 0 Arthrobacter simpler (ATCC- 6496) 0 0 Arthrobacter ureafaciem (ATCC- 7562 0 0 Escherichia intermedia (A-21) 0. 2 0. l 5.
  • ATC 3-6466
  • Arthrobacter simpler ATCC- 6496
  • Arthrobacter ureafaciem ATCC- 7562 0 0 Escherichia intermedia (A-21) 0. 2 0. l 5.
  • 9 Escherichia coli HAM-1239 ATOC-15289) 0- 1 0 2.
  • 9 Aeromo'mzs hydrophz'la (1AM- 0.
  • Serrutia marcescens (ATCC- 14227) 0 Sermlia marcescens (ATCC- 2 Cilglomonas gelida (ATCC- BacizzaRHdil'i'sYiAiI-iibi')I:I: Bacillus megutherium (3-205-2) Vibn'o melsclmikovi (LAM-1039) Vibrio tyrogenes (IAM-lOSO) Flavobacterium harrisonii (A'ICC- Psiudomoms perlurida (ATCC- 1 53 Stzgalgflococcus citreus -(ATOC l Staphylococcus aureus (1AM- o o o 0 Q0000 Micrococcus varians (ATCC399) Migggoccus lysodeikticus (ATCC- Myco liifi'lihiiiiziiiK'i dd iisiI Mycoplona di
  • N, A, S, OM, YO Identification numbers of the Institute for Food Microbiology, Chiba University, Japan.
  • ATCC Identification number of the American Type Culture 001- lection, Washington, D.O.
  • Organic bases which have been used successfully in the method of the invention include purine bases, such as purine, adenine, hypoxanthine, Xanthine, guanine, 2- arninopurine, 2,6-diamino-purine, 6-dirnethy-laminopurine, benzyladenine, 6-methylamino-purine, or kinetin; and pyrimidine bases, such as uracil, S-hydroxymethyluracil, cytosine, thymine, or barbituric acid.
  • purine bases such as purine, adenine, hypoxanthine, Xanthine, guanine, 2- arninopurine, 2,6-diamino-purine, 6-dirnethy-laminopurine, benzyladenine, 6-methylamino-purine, or kinetin
  • pyrimidine bases such as uracil, S-hydroxymethyluracil, cytosine, thymine,
  • Suitable donors of ribose-5'-phosphate or deoxyribose- 5-phosphate radicals are 5-adenylic acid, 5-inosinic acid, 5-xanthylic acid, 5'-guanylic acid, 5-cytidylic acid, 5-uridylic acid, and other 5'-ribonucleotides; 5-deoxycytidylic acid, 5-deoxythymidylic acid, 5-deoxyguanylic acid, 5'-deoxyadenylic acid and other 5-deoxyribonucleotides.
  • Such 5-nucle0tides as 5'-cytidylic acid or 5'- uridylic acid, which are produced by the hydrolysis of nucleic acid and are not employed as flavoring agents, are useful donors of the ribose-S'-phosphate radical for the synthesis of 5'-in0sini-c acid and 5'-guanylic acid which are useful seasoning agents.
  • the bacteria employed as an enzyme source can be prepared by submerged culture or stationary culture in synthetic or natural media at 20 to 40 C., for 15 to 50 hours.
  • the enzyme source can be admixed to the reaction mixture in the form of a culture broth, as living cells, dried cells, or cell extracts.
  • the enzyme reaction of the present invention may be carried out in an aqueous medium.
  • Insoluble organic bases dissolve in the solution as the reaction proceeds.
  • the reaction proceeds in the pH range from to 10, and best between pH 7 and 9.
  • the reaction may be carried out at temperatures from 30 to 60 C., and preferably from 40 to 50 C.
  • 5-nucleotides synthesized according to the method of the invention may be isolated from the reaction mixture by such conventional methods as ion exchange chromatography or precipitation. After removal of bacterial cells, the reaction mixture may be passed over a column packed with an anion exchange resin in the (Cl) form (such as Dowex 1X4). The resin is then washed with water, the nucleotide adsorbed on the column is eluted by a suitable solvent, and the fractions containing the desired nucleotide are neutralized, concentrated, and the nucleotide is precipitated by alcohol. 5'-nucleotides are obtained as crude crystals of an alkali metal salt.
  • the nucleotides synthesized may be identified by conventional methods such as detection of the phosphate ester linkage, carbazole reaction, spectrophotometric metaperiodate oxidation, detection of inorganic phosphate liberated with snake venom 5-nucleotidase, or paper electrophoresis in acetic acid as a solvent.
  • the nucleotide synthesized from organic bases by the method of this invention as described hereinafter were identified as 5'-isomers by the methods described above.
  • Example 1 20 ml. of a nutrient medium containing 1.0% meat extract, 1.0% peptone, 1.0% glucose, and 0.5% sodium chloride (pH 7.0) were placed in a 500 ml. shaking flask, and sterilized at 115 C. for 10 minutes. The medium was inoculated with Pseudomonas trifolii (ATCC-14537) and cultured aerobically at 30 C. for 20 hours. The bacterial cells were collected by centrifuging and suspended in distilled water.
  • a nutrient medium containing 1.0% meat extract, 1.0% peptone, 1.0% glucose, and 0.5% sodium chloride (pH 7.0) were placed in a 500 ml. shaking flask, and sterilized at 115 C. for 10 minutes. The medium was inoculated with Pseudomonas trifolii (ATCC-14537) and cultured aerobically at 30 C. for 20 hours. The bacterial cells were collected by centrifuging and suspended in distilled water.
  • the bacterial cells were removed from the reaction solution by centrifuging, the supernatant liquid obtained was adjusted to pH 9.0, and the solution was passed over a column packed with 200 ml. of an anion exchange resin of the chloride type (Dowex 1X4).
  • the column was washed with about 3 liters of water in which unreacted adenine was eluted, and then with 0.005 M acetate butler solution containing 0.146% soduim chloride (pH 5.5).
  • the butler eluate was collected in 200 ml. fractions. Nucleosides were eluted first.
  • Example 2 A cell suspension of Pseudomonas trifolii ATCC.14537 was prepared as described in Example 1.
  • 1/2 M-acetate bufier solution was used for adjusting the pH between 4 and 6.
  • 1/2 M-Tris-hydrochloride bufier solution was used for a pH oi 7.0 to 10.0.
  • Example 3 40 ml. batches of an aqueous solution, each batch containing 67.5 mg. adenine, 715 mg. disodium-5-uridylate and 136.1 mg. potassium dihydrogen phosphate were mixed with 10 ml. of a cell suspension prepared as in Example 1 and containing 150 ml. all substance on a dry basis. The pH of the mixtures was adjusted to 9.0,
  • hypoxanthine 68.1 mg. of hypoxanthine and 75.6 mg. of
  • a cell suspension of Alcaligenes metalcaligenes was prepared in the manner described in Example 1 and employed in converting 1.35 g. adenine as described in Example 1.
  • Example 5 A cell suspension of Pseudomonas trifolii (ATCC- 12287) was prepared as described in Example 1.
  • aqueous solution containing 1.36 g. hypoxanthine, and 14.3 g. disodium-5'-uridylate was treated with the cell suspension as described hereinabove at 4045 C.
  • the reaction solution then contained 0.22 g./dl. 5-inosinic acid (63.5% based on the hypoxanthine).
  • a concentration of 0.18 g./dl. .5'-inosinic acid was obtained (51.7% based on the origi- The solution was worked up, and 2.58 g. sodium-5- inosinate were obtained.
  • Example 6 A cell suspension of Pseudomonas trifolii ATCC12287 was prepared as described in Example 1.
  • Example 7 Cell suspension of the bacteria listed in the following table was prepared as described in Example 1.
  • a cell suspension of Pseudomonas trifoliz (ATCC 14537) was prepared as described in Example 1.
  • Aqueous solutions were prepared to contain per ml. batch, 715 mg. disodium-5'-uridylate, 136.1 mg. potassium dihydrogen phosphate, and one of the following bases: 60.1 mg. purine, 99.1 mg. Z-amino purine (nitrate), 208.2 mg. 2,6-diaminopurine (sulfate), 64.5 mg. barbituric acid, 63.1 mg. thymine, 74.6 mg. 6-methylaminopurine, 81.6 mg. G-dimethylaminopurine, 113.2 mg. benzyladenine, 107.6 mg. 6-furfurylaminopurine.
  • Each batch was mixed with 10 ml. of the cell suspension 150 mg. dry cell substance), and the mixture was incubated statically at pH 9.0 and at 4045 C. for 3-6 hours.
  • Example 8 The concentrations and yields of the 5-nucleot1de
  • Example 9 Cell suspensions of Pseudomonas trifolii (ATCC 12287) and Alcaligenes viscolactis (ATCC9036) were prepared as described in Example 1.
  • Aqueous solutions respectively containing 67.6 mg. adenine, 68.1 mg. hypoxanthine, 75.6 mg. guanine, and 76.1 mg. xanthine, and each containing 715 mg. disodium- 5-cytidylate were incubated with the cell suspensions as described in Example 7.
  • 5'-nucelotides corresponding to synthesized are listed below.
  • Example 11 Three reaction mixtures were prepared each from 40 ml. of a solution containing 588 mg. diammonium-5- thymidylate, 136.1 mg. of potassium dihydrogen phosphate and respectively containing 67.6 mg. adenine, 68.1 mg, hypoxanthine, and 75.6 mg. guanine, with 10 ml. of a cell suspension of Pseudomonas trifolii ATCC14537 mg. dry cell matter) prepared as described in Example 1, and the mixtures were incubated at pH 9.0 and at 40-45 C. for 3-6 hours.
  • '-deoxynucleotides were obtained as follows:
  • Example 12 Pseudomonas trifolii (ATCC-14537) was grown as described in Example 1, except that the culture medium contained 4% glucose, 0.1% KH PO 0.04% MgSO 7I-I O, 2 p.p.m Fe++, 2 ppm. Mn++, 0.5% amino acid mixture, 0.5 soybean meal hydrolysate, and 2% l-pyroglutamic acid (pH 7.7).
  • hypoxanthine formed was eluted with 18 liters of 0.01 M acetate bufifer (pH 5.5) containing 0.059% sodium chloride, and the thymine riboside-S'-monophosphate was obtained next by elution with 9 liters of a solution containing 0.29% sodium chloride in the same buffer.
  • the residual 5'- inosinic acid was recovered last with 4 liters of 2-N hydrochloric acid.
  • the eluate containing the thymine riboside-5-monophosphate was neutralized with sodium hydroxide, concentrated in vacuo, and filtered to remove inorganic salts. It was then diluted with alcohol.
  • a process for preparing a 5'-nucleotide having a desired purine or pyrimidine base component which com prises contacting an enzyme source with an aqueous medium containing the organic base corresponding to the desired base component and a 5-nucleotide other than that to be prepared and having a base component selected from the group consisting of a purine and pyrimidine which is different from said desired base component until the desired 5-nucleotide is formed; and recovering the formed 5'-nucleotide, said enzyme source being capable of producing a 5-nucleotide selected from the group consisting of adenylic acid and inosinic acid when in contact with an aqueous solution containing 0.135 g.
  • said enzyme source being prepared from a microorganism selected from the genera Alcaligenes, Escherichia, Aerobacter, Pseudomonas,
  • said. enzyme source is a cell material of a bacterium selected from the group consisting of Alcaligenes metacaligenes AN-3, Alcaligenes viscolactis ATCC-9036, Escherichia.
  • said purine base is a member of the group consisting of purine, adenine, hypoxanthine, xanthine, guanine, 2-aminopurine, 2, fi-diaminopurine, 6-methylaminopurine, 6-dimethylaminopurine, G-furfurylaminopurine, benzyladenine, and kinetin.
  • 5'- deoxyribonucleotide is a member of the group consisting of 5-deoxycytidylic acid, 5'-deoxythymidylic acid, 5-deoxyguanylic acid, and 5-deoxyadenylic acid.
  • aqueous medium includes ions of phosphoric acid.
  • said cell material essentially consists of living cells of said bacterium, said aqueous medium is at a pH between 5 and.
  • said organic base is a member of the group consis-ting of purine, adenine hypoxanthine, xanthine, guanine, 2-aminopurine, 2,6-diaminopurine, 6-methylaminopurine, 6-dimethylaminopurine, 6-furfurylaminopurine, benzyladenine, and kinetin, uracil, S-hydroxymethyluracil, cytosine, thymine, and barbituric acid, and said other 5- nucleotide is a member of the group consisting of5' adenylic acid, 5'-inosinic acid, 5'-xanthylic acid, 5'-guanylic acid, 5'-cytidylic acid, and 5-uridylic acid, 5'-deoxycytidylic acid, 5'-deoxythymidylic acid, 5-deoxyguanylic acid, and 5'-de

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US399082A 1963-09-27 1964-09-24 Process for preparing 5'-nucleotides Expired - Lifetime US3296087A (en)

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DE (1) DE1445456A1 (enrdf_load_stackoverflow)
FR (1) FR1550952A (enrdf_load_stackoverflow)
GB (1) GB1021962A (enrdf_load_stackoverflow)
NL (1) NL6411078A (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3382233A (en) * 1964-05-19 1968-05-07 Kyowa Hakko Kogyo Kk Process for producing 5'-guanylic acid
US3408206A (en) * 1965-01-11 1968-10-29 Ajinomoto Kk 5'-nucleotides seasoning agents
US3457254A (en) * 1965-10-09 1969-07-22 Asahi Chemical Ind Process for preparing nucleosides
US3458398A (en) * 1965-07-20 1969-07-29 Kyowa Hakko Kogyo Kk Process for producing inosinic acid
US3620921A (en) * 1967-03-18 1971-11-16 Kyowa Hakko Kogyo Kk Process for producing 5{40 -inosinic acid and 5{40 -guanylic acid nucleotides
US5106585A (en) * 1983-03-02 1992-04-21 Mitsui Toatsu Chemicals, Inc. Method and apparatus for cleaving deoxyribonucleic acid
RU2179188C2 (ru) * 2000-03-03 2002-02-10 Институт биоорганической химии им. М.М. Шемякина и Ю.А. Овчинникова РАН СПОСОБ ПОЛУЧЕНИЯ РЕКОМБИНАНТНОЙ ПУРИННУКЛЕОЗИД-ФОСФОРИЛАЗЫ, РЕКОМБИНАНТНАЯ ПЛАЗМИДНАЯ ДНК pERPUPHO1 И ШТАММ ESCHERICHIA COLI BL21(DE3)/pERPUPHO1 ДЛЯ ЕГО ОСУЩЕСТВЛЕНИЯ

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3382233A (en) * 1964-05-19 1968-05-07 Kyowa Hakko Kogyo Kk Process for producing 5'-guanylic acid
US3408206A (en) * 1965-01-11 1968-10-29 Ajinomoto Kk 5'-nucleotides seasoning agents
US3458398A (en) * 1965-07-20 1969-07-29 Kyowa Hakko Kogyo Kk Process for producing inosinic acid
US3457254A (en) * 1965-10-09 1969-07-22 Asahi Chemical Ind Process for preparing nucleosides
US3620921A (en) * 1967-03-18 1971-11-16 Kyowa Hakko Kogyo Kk Process for producing 5{40 -inosinic acid and 5{40 -guanylic acid nucleotides
US5106585A (en) * 1983-03-02 1992-04-21 Mitsui Toatsu Chemicals, Inc. Method and apparatus for cleaving deoxyribonucleic acid
RU2179188C2 (ru) * 2000-03-03 2002-02-10 Институт биоорганической химии им. М.М. Шемякина и Ю.А. Овчинникова РАН СПОСОБ ПОЛУЧЕНИЯ РЕКОМБИНАНТНОЙ ПУРИННУКЛЕОЗИД-ФОСФОРИЛАЗЫ, РЕКОМБИНАНТНАЯ ПЛАЗМИДНАЯ ДНК pERPUPHO1 И ШТАММ ESCHERICHIA COLI BL21(DE3)/pERPUPHO1 ДЛЯ ЕГО ОСУЩЕСТВЛЕНИЯ

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GB1021962A (en) 1966-03-09
NL6411078A (enrdf_load_stackoverflow) 1965-03-29
FR1550952A (enrdf_load_stackoverflow) 1968-12-27

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