DE2752380A1 - 2,5-Di:hydro-2(4)-methyl-5-oxo-furan-2-acetic acid prepn. - by biological cresol co-oxidn. in medium contg. chloro-benzoate replaced by chlorophenol - Google Patents

2,5-Di:hydro-2(4)-methyl-5-oxo-furan-2-acetic acid prepn. - by biological cresol co-oxidn. in medium contg. chloro-benzoate replaced by chlorophenol

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Publication number
DE2752380A1
DE2752380A1 DE19772752380 DE2752380A DE2752380A1 DE 2752380 A1 DE2752380 A1 DE 2752380A1 DE 19772752380 DE19772752380 DE 19772752380 DE 2752380 A DE2752380 A DE 2752380A DE 2752380 A1 DE2752380 A1 DE 2752380A1
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Prior art keywords
cresol
chloro
methyl
benzoate
furan
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DE19772752380
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German (de)
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Manfred Hellwig
Hans-Joachim Prof Dr Knackmuss
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Helmholtz Zentrum Muenchen Deutsches Forschungszentrum fuer Gesundheit und Umwelt GmbH
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Helmholtz Zentrum Muenchen Deutsches Forschungszentrum fuer Gesundheit und Umwelt GmbH
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Priority to DE2548454A priority Critical patent/DE2548454C2/en
Priority claimed from DE2548454A external-priority patent/DE2548454C2/en
Application filed by Helmholtz Zentrum Muenchen Deutsches Forschungszentrum fuer Gesundheit und Umwelt GmbH filed Critical Helmholtz Zentrum Muenchen Deutsches Forschungszentrum fuer Gesundheit und Umwelt GmbH
Priority to DE19772752380 priority patent/DE2752380A1/en
Priority to DE19772752379 priority patent/DE2752379A1/en
Publication of DE2752380A1 publication Critical patent/DE2752380A1/en
Ceased legal-status Critical Current

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    • 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
    • C07D307/58—One oxygen atom, e.g. butenolide
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/20—Bacteria; Culture media therefor
    • C12N1/205—Bacterial isolates
    • 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
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/38—Pseudomonas

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Virology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)

Abstract

Parent patent discloses a process for preparing difficulty available or pure optical isomers of unsatd., cyclic, alpha,beta-dihydroxy-monocarboxylic acids; substd. unsatd., aliphatic dicarboxylic acids and substd. unsatd. aliphatic monohydroxy-dicarboxylic acids and lactones. In this addition, (+)-2,5-dihydro-4-methyl-, (I), and (+)-2,5-dihydro-2-methyl-5-oxo-furan-2-acetic acid (II) are prepd. by a cresol co-oxidn. process comprising: (a) cultivating a biologically active suspension of a Pseudomonas bacteria of strain B 13 on a mineral salt soln. contg. a 3-chloro-benzoate as only C- and energy-source; (b) adapting the bacterial strain to 4-chlorophenol by continuously replacing the 3-chloro-benzoate according to a linear gradient by an equimolar concn. of 4-chloro-phenol until constant cell density E564 = 1.8 is reached; (c) adding a cresol and co-oxidn. (I) is obtd. on adding o-cresol; (II) on adding p-cresol and a (I)/(II) isomer mixt. on adding m-cresol. The metabolites dissolved in culture liq. are recovered by sepg. the bacterial cells or by preparative chromatography. (I) can be prepd. in quantitative yields; (II) in 95% yield and the isomer mixt. in 73% and 14% yields of isomers (I) and (II).

Description

Verfahren zur Herstellung von auf chemischem Process for the production of on chemical

Wege schwer zugänglichen, organischen Verbindungsspecies Zusatz zu Patent ....... Ways to add to difficult to access, organic compound species Patent .......

Patentanmeldung P 25 48 454. 2-42 Beschreibung: Die Erfindung betrifft ein Verfahren nach dem Oberbegriff des Patentanspruchs.Patent application P 25 48 454. 2-42 Description: The The invention relates to a method according to the preamble of the claim.

Der Erfindung liegt die Aufgabe zugrunde, ein Verfahren zu schaffen, mit welchem auf chemischen Wege schwer zugängliche organische Verbindungen, wie sie im Oberbegriff des Patentanspruchs erwähnt werden, in einfacher Weise, in reinem Zustand (ohne nichtisomere Nebenprodukte) und mit verhältnismäßig hoher Ausbeute hergestellt werden können. VerhåtnismäBig hohe Ausbeuten bedeuten in diesem Falle Ausbeuten von mehr als 50 7o. The invention is based on the object of creating a method with which organic compounds that are difficult to access chemically, such as they are mentioned in the preamble of the claim, in a simple manner, in pure form State (without non-isomeric by-products) and with a relatively high yield can be produced. Relatively high yields mean in this case Yields greater than 50 7o.

Die Lösung dieser Aufgabe erfolgt erfindungsgemäß durch die Verfahrensschritte: a) Anzucht einer biologisch aktiven Suspension von Pseudomas-Bakterien des Stammes B 13 auf einer 3-Chlor-benzoat als einzige Kohlenstoff- und Energiequelle (Wachstumssubstrat) enthaltenden Mineralsalzlösung; b) Adaptation des Bakterienstanimes an 4-Chlorphenol durch kontinuierliches Ersetzen des 3-Chlor-benzoats nach einem linearen Gradienten durch eine äquimolare Konzentration von 4-Chlor-phenol bis eine konstante Zelldichte von E564 = 1, 8 erreicht ist; c) Zugabe eines Kresols und Cooxidation desselben, ,im Falle von o-Kresol zu (+) -2, 5-Dihydro-4-methyl-5-oxo-furan-2-essigsäure in praktisch quantitativer Ausbeute, im Falle von p-Kresol zu der isomeren (+)-2, 5-Dihydro-2-methyl 5-oxo-furan-2-essigs.iure in 95% ige r Ausbeute, im Falle von m-Kresol zu einem Gemisch 73%iger respektive 14% iger Ausbeute der genannten Isomeren; d) Gewinnung des oder der in der Kulturflüssigkeit gelösten Metabolite durch Abtrennen der Bakterienzellen wie ip Patent ....... This object is achieved according to the invention by the process steps: a) Cultivation of a biologically active suspension of Pseudomas bacteria of the strain B 13 on a 3-chloro-benzoate as the only carbon and energy source (growth substrate) containing mineral salt solution; b) Adaptation of the bacteria set to 4-chlorophenol by continuously replacing the 3-chloro-benzoate according to a linear gradient by an equimolar concentration of 4-chloro-phenol until a constant cell density of E564 = 1.8 is reached; c) addition of a cresol and co-oxidation of the same, , in the case of o-cresol to (+) -2, 5-dihydro-4-methyl-5-oxo-furan-2-acetic acid in practically quantitative yield, in the case of p-cresol to the isomeric (+) - 2, 5-dihydro-2-methyl 5-oxo-furan-2-acetic acid in 95% yield, in the case of m-cresol to a Mixture of 73% or 14% yield of the isomers mentioned; d) extraction of the metabolite or metabolites dissolved in the culture fluid by separating the bacterial cells like ip patent .......

(Patentanmeldung P 25 48 454. 2-42) beschrieben oder durch präparative ChromatogrtpJic. (Patent application P 25 48 454. 2-42) described or by preparative ChromatogrtpJic.

Die Erfindung wird anhand des folgenden Beispiels näher erläutert: Beispiel: Herstellung von (+)-2, 5-Dihydro-4-methyl- und (+)-2, 5-Dihydro-2-methyl-5-oxo-furan-2-essigsäure durch Cooxidation von Kresolen.The invention is explained in more detail using the following example: Example: Preparation of (+) - 2, 5-dihydro-4-methyl- and (+) - 2, 5-dihydro-2-methyl-5-oxo-furan-2-acetic acid by co-oxidation of cresols.

Zur Anzucht von Pseudomonos-Bakterien des Stammes B 13 wurden zunSchst folgende Stammlösungen erstellt: Stammlösung 1: 70 g Na2HPO4 x 12 H2O 10 g KH2PO4 in 1000 ml Wasser Stammlösung 2: 100 g (NH4)2SO4 5, 0 g Ca(NO3)2 x4H2O 1, 0 g Fe(III)-Amonlumcitrat 20 g MgSO4x 7H20 100 ml Spurenelementlösung nach N.Pfennig und K. D. Lippert (Arch. Mikrobiol., Vol. 55 (1966), S. 245-256), allerdings ohne Eisensalze und Äthylendiamintetraessigsäure in 1000 ml wäßriger Lösung. For the cultivation of Pseudomonos bacteria of the strain B 13 were initially The following stock solutions are created: Stock solution 1: 70 g Na2HPO4 x 12 H2O 10 g KH2PO4 in 1000 ml of water stock solution 2: 100 g (NH4) 2SO4 5, 0 g Ca (NO3) 2 x4H2O 1, 0 g Fe (III) ammonium citrate 20 g MgSO4x 7H20 100 ml trace element solution according to N.Pfennig and K. D. Lippert (Arch. Mikrobiol., Vol. 55 (1966), pp. 245-256), but without iron salts and ethylenediaminetetraacetic acid in 1000 ml of aqueous solution.

Stammlösung 3:156,6 g 3-Chlorbentoesäure in 1000 ml wäßriger Lösung, mit NaOH auf PH 7, 5 eingestellt.Stock solution 3: 156.6 g of 3-chlorobentoic acid in 1000 ml of aqueous solution, Adjusted to pH 7.5 with NaOH.

Das komplette Mineralsalz -Chlorb.anzoat-medium enthielt im Liter 100 ml der Stammlösung 1 und jeweils 10 ml der Stammlösungen 2 und 3. The complete mineral salt - chlorine anzoate medium contained in one liter 100 ml of stock solution 1 and 10 ml each of stock solutions 2 and 3.

einem Die Pseudomonas-Bakterien wurden in/200 ml Chemostaten kultiviert. The Pseudomonas bacteria were cultivated in / 200 ml chemostats.

Die Verdünnungsrate wurde auf 0, 4 x 10 h eingestellt und das 3-Chlorbenzoat innerhalb von 10 Tagen nach einem linearen Gradienten durch eine äquimolare Konzentration an4-Chlorphenol O-910 mM ersetzt. Bei weiterer kontinuierlicher Kultivierung auf 50 mM 4-Chlor-phenol wurde schließlich eine konstante Zelldichte von E564= 1,8 erreicht.The dilution rate was set to 0.4 × 10 h and the 3-chlorobenzoate within 10 days of a linear gradient through an equimolar concentration an4-chlorophenol O-910 mM replaced. With further continuous cultivation on With 50 mM 4-chlorophenol, a constant cell density of E564 = 1.8 was finally achieved.

Mit 100 ml dieser kontinuierlichen Kultur wurde ein 5 1 Fermenter mit 0, 9 1 Mineralmedium der o. g. Art beimpft. Frisches Mineralmedium, welches 100 mM 4-Chlorphenol und 100 mM NaOH enthielt, wurde mittels einer Schlauchpumpe zugespeist. Die Konzentration an 4-Chlorphenol wurde ständig kontrolliert und im Bereich von 0, 01 bis 0, 15 mM gehalten.With 100 ml of this continuous culture, a 5 liter fermenter with 0.9 1 mineral medium of the above Kind inoculated. Fresh mineral medium which 100 mM 4-chlorophenol and 100 mM NaOH contained, was by means of a peristaltic pump fed. The concentration of 4-chlorophenol was constantly monitored and im Maintained range from 0.01 to 0.15 mM.

Die auf 4-Chlorphenol angezogenen Zellen cooxidierten leicht o-, m- oder p-Kresol. Aus o-Kresol entstand praktisch quantitativ (+)-2, 5-Dihydro-4-methyl-5-oxo-furan-2-essigsäure, aus p-Kresol die isomere (+)-2, 5-Dihydro- 2 -methyl- 5-oxo-furan-2 -e s sig säure in 957ciger Ausbeute.The cells grown on 4-chlorophenol co-oxidized slightly o-, m- or p-cresol. From o-cresol, (+) - 2, 5-dihydro-4-methyl-5-oxo-furan-2-acetic acid was formed practically quantitatively, from p-cresol the isomeric (+) - 2, 5-dihydro-2-methyl-5-oxo-furan-2-acetic acid in 957 yield.

Mit m-Kresol als Substrat entstand ein Gemisch der beiden genannten Verbindungen in 737ciger respektive l47ciger Ausbeute. Bei einer Zellkonzentration entsprechend 4, 1 g Protein pro Liter wurden etwa 6 m mol Kresol/hx Ltr. umgesetzt. Bis zu einer Produktkonzentration von etwa 10 g pro Liter verlief die Cooxidation der Kresole ungehemmt.With m-cresol as the substrate, a mixture of the two was produced Compounds in 737 or 147 yield. At a cell concentration corresponding to 4.1 g protein per liter, about 6 m mol cresol / hx liter were converted. The co-oxidation took place up to a product concentration of about 10 g per liter the cresole uninhibited.

Die Produkte wurden wie beschrieben aus den Kulturflüssigkeiten isoliert, bei Vorliegen eines Isomeren-Gemisches durch präparative Chromatographie getrennt und mit den ahentischen Proben aus der Cooxidation von Methylbrenzcatechinen identifiziert (Schmelzpunkte und Mischproben, UV- und IR-Spektren).The products were isolated from the culture liquids as described, separated by preparative chromatography if an isomer mixture is present and identified with the authentic samples from the co-oxidation of methylcatechols (Melting points and mixed samples, UV and IR spectra).

Claims (1)

Patentanspruch: Verfahren zur Herstellung von auf chemischewn Wege schwer zugänglichen, organischen Verbindungsspecies bzw. reinen optischen Isomeren aus den Gruppen ungesättigte, zyklische α-ß -ß -Dihydroxy monoc arbonsäuren substituierte, ungesättigte, aliphatische Dicarbonsäuren substituierte, ungesättigte, aliphatische Monohydroxy-dicarbon säuren und deren Lactone, wobei in einem ersten Verfahrens abschnitt ein Bakterienstamm auf einem Wachstums substrat angezogen wird, das eine mit einem unphysiologischen Substituenten versehene, aromatische Verbindung als Kohlenstoff- und Energiequelle enthält und während der Verwertung des Wachtumssubstrates (Vermehrung der Bakterienzellen) der unphysiologische Substituent durch eine anionische Eliminierungsreaktion aus der aromatischen Verbindung abgetrennt wird, und in einem zweiten Verfahrensabschnitt eine zum Wachstums substrat strukturanaloge Verbindung oder deren Isomeresizugegeben und metabolosiert wird, die im Gegensatz zum Wachstums substrat ein Strukturelement (einen Substituenten) enthält, das (der) aufgrund seiner unterschiedlichen Polarität, es (er) ist gegenüber dem eliminierbaren Substituenten im Wachstums substrat nichtisoelektronisch, während der Cooxidation der beiden aromatischen Verbindungen nicht entsprechend eliminiert werden kann, und daß der Metabolit der nicht vollständig abbaubaren, strukturanalogen Verbindung im Substrat akkumulieren gelassen wird nach Patent .. .. ... (Patentanmeldung P 25 48 454. 2-42), gekennzeichnet durch die Verfahrensschritte a) Anzucht einer biologisch aktiven Suspension von Pseudomonas-Bakterien des Stammes B 13 auf einer 3-Chlor-benzoat als einzige Kohlenstoff- und Energiequelle (Wachstumssubstrat) enthaltenden Mineralsalzlösung; b) Adaptation des Bakterienstammes an 4-Chlorphenol durch kontinuierliches Ersetzen des 3-Chlor-benzoats nach einem linearen Gradienten durch eine äquimolare Konzentration von 4-Chlor-phenol bis eine konstante Zelldichte von E564 = 1, 8 erreicht ist; c) Zugabe eines Kresols und Cooxidation desselben, im Falle von o-Kresol zu (+) -2, 5-Dihydro-4-methyl-5-oxo-furan-2-essigsäure in praktisch quantitativer Ausbeute, im Falle von p-Kresol zu der isomeren (+)-2, 5-Dihydro-Z-methyl-5-oxo-furan-2-essigsäure in 95%iger Ausbeute, im Falle von m-Kresol zu einem Gemisch in 73%iger respektive 14%iger Ausbeute der genannten Isomeren; d) Gewinnung des oder der in der Kulturflüssigkeit gelösten Metabolite durch Abtrennen der Bakterienzellen wie in Patent ....Claim: Process for the production of chemically Difficult to access, organic compound species or pure optical isomers from the groups unsaturated, cyclic α-β-β-dihydroxy monocarboxylic acids substituted, unsaturated, aliphatic dicarboxylic acids substituted, unsaturated, aliphatic monohydroxydicarboxylic acids and their lactones, with a first Procedure section a bacterial strain is grown on a growth substrate, the one provided with an unphysiological substituent, aromatic compound contains as a carbon and energy source and during the utilization of the growth substrate (Multiplication of bacterial cells) the unphysiological substituent by an anionic one Elimination reaction is separated from the aromatic compound, and in one second process stage a compound structurally analogous to the growth substrate or the isomeres of which is added and metabolized, in contrast to growth substrate contains a structural element (a substituent) which due to its different polarity, it (he) is opposite the eliminable substituent non-isoelectronic in the growth substrate, while the two aromatic co-oxidation Compounds can not be eliminated appropriately, and that the metabolite of the Not completely degradable, structurally analogous compound accumulate in the substrate is left according to patent .. .. ... (patent application P 25 48 454. 2-42), characterized by the process steps a) growing a biologically active suspension of Pseudomonas bacteria of strain B 13 on a 3-chloro-benzoate as the only carbon and mineral salt solution containing energy source (growth substrate); b) Adaptation of the bacterial strain to 4-chlorophenol through continuous replacement of 3-chloro-benzoate according to a linear gradient through an equimolar concentration from 4-chloro-phenol until a constant cell density of E564 = 1.8 is reached; c) Addition of a cresol and co-oxidation of the same, in the case of o-cresol to (+) -2, 5-dihydro-4-methyl-5-oxo-furan-2-acetic acid in practically quantitative yield, in the case of p-cresol to the isomeric (+) - 2, 5-dihydro-Z-methyl-5-oxo-furan-2-acetic acid in 95% yield, in the case of m-cresol to a mixture in 73%, respectively 14% yield of the isomers mentioned; d) Obtaining the one or more in the culture liquid dissolved metabolites by separating the bacterial cells as in patent ... (Patentanmeldung P 25 48 454. 2-42) beschrieben oder durch präparative Chromatographie. (Patent application P 25 48 454. 2-42) described or by preparative Chromatography.
DE19772752380 1975-10-29 1977-11-24 2,5-Di:hydro-2(4)-methyl-5-oxo-furan-2-acetic acid prepn. - by biological cresol co-oxidn. in medium contg. chloro-benzoate replaced by chlorophenol Ceased DE2752380A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE2548454A DE2548454C2 (en) 1975-10-29 1975-10-29 Process for the preparation of (+) - 2,5-dihydro-2-methyl-5-oxo-furan-acetic acid- (2) or of 1,2-dihydro-cis-1,2-dihydroxy-naphthoic acid- (2)
DE19772752380 DE2752380A1 (en) 1975-10-29 1977-11-24 2,5-Di:hydro-2(4)-methyl-5-oxo-furan-2-acetic acid prepn. - by biological cresol co-oxidn. in medium contg. chloro-benzoate replaced by chlorophenol
DE19772752379 DE2752379A1 (en) 1975-10-29 1977-11-24 2,5-Di:hydro-2,4-di:methyl-5-oxo-furan-2-acetic acid prepn. - by bacterial co-oxidation of 3,5-di:methyl-benzoate in mineral salt nutrient medium contg. di:chloro-benzoate

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2548454A DE2548454C2 (en) 1975-10-29 1975-10-29 Process for the preparation of (+) - 2,5-dihydro-2-methyl-5-oxo-furan-acetic acid- (2) or of 1,2-dihydro-cis-1,2-dihydroxy-naphthoic acid- (2)
DE19772752380 DE2752380A1 (en) 1975-10-29 1977-11-24 2,5-Di:hydro-2(4)-methyl-5-oxo-furan-2-acetic acid prepn. - by biological cresol co-oxidn. in medium contg. chloro-benzoate replaced by chlorophenol

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DE2752380A1 true DE2752380A1 (en) 1979-05-31

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0567102A2 (en) * 1992-04-22 1993-10-27 Canon Kabushiki Kaisha Method of biologically decomposing phenol or furan compounds by microorganisms
US5863789A (en) * 1993-09-30 1999-01-26 Canon Kabushiki Kaisha Microorganism-holding carrier and method for remediation of soil employing the carrier
US6096530A (en) * 1992-04-22 2000-08-01 Canon Kabushiki Kaisha Pseudomonas cepacia strain isolated from termite intestines that degrades trichlorethylene and furan compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NICHTS-ERMITTELT *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0567102A2 (en) * 1992-04-22 1993-10-27 Canon Kabushiki Kaisha Method of biologically decomposing phenol or furan compounds by microorganisms
EP0567102A3 (en) * 1992-04-22 1994-11-23 Canon Kk Method of biologically decomposing phenol or furan compounds by microorganisms.
US6096530A (en) * 1992-04-22 2000-08-01 Canon Kabushiki Kaisha Pseudomonas cepacia strain isolated from termite intestines that degrades trichlorethylene and furan compounds
US5863789A (en) * 1993-09-30 1999-01-26 Canon Kabushiki Kaisha Microorganism-holding carrier and method for remediation of soil employing the carrier

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