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WO1996037620A3 - Verfahren zur gewinnung von acyloinen, dafür geeignete pyruvat-decarboxylase sowie deren herstellung und dna-sequenz des für diese kodierenden pdc-gens - Google Patents

Verfahren zur gewinnung von acyloinen, dafür geeignete pyruvat-decarboxylase sowie deren herstellung und dna-sequenz des für diese kodierenden pdc-gens Download PDF

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Publication number
WO1996037620A3
WO1996037620A3 PCT/DE1996/000928 DE9600928W WO9637620A3 WO 1996037620 A3 WO1996037620 A3 WO 1996037620A3 DE 9600928 W DE9600928 W DE 9600928W WO 9637620 A3 WO9637620 A3 WO 9637620A3
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WO
WIPO (PCT)
Prior art keywords
pyruvate decarboxylase
obtaining
gene coding
phenylacetylcarbinole
acyloins
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/DE1996/000928
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English (en)
French (fr)
Other versions
WO1996037620A2 (de
Inventor
Heike Bruhn
Martina Pohl
Katrin Mesch
Maria-Regina Kula
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.)
Forschungszentrum Juelich GmbH
Original Assignee
Forschungszentrum Juelich GmbH
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 Forschungszentrum Juelich GmbH filed Critical Forschungszentrum Juelich GmbH
Priority to EP96919594A priority Critical patent/EP0828841A2/de
Priority to AU58102/96A priority patent/AU714414B2/en
Priority to BR9608798A priority patent/BR9608798A/pt
Priority to JP8535270A priority patent/JPH11505710A/ja
Publication of WO1996037620A2 publication Critical patent/WO1996037620A2/de
Publication of WO1996037620A3 publication Critical patent/WO1996037620A3/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/52—Genes encoding for enzymes or proenzymes
    • 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
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • C12P7/26—Ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
    • 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
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/88—Lyases (4.)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Plant Pathology (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)

Abstract

Die Erfindung bezieht sich auf ein Verfahren zur Gewinnung einer Pyruvat-decarboxylase durch Isolierung aus einem Produzenten-Organismus. Die Pyruvat-decarboxylase ist zur Bildung von (R)-(-)-Phenylacetylcarbinol (I) in » 95 % Enantiomereneinheit mit einem Produktverhältnis von I zu 2-Hydroxypropiophenon von » 95 % befähigt. Außerdem besitzt die Pyruvat-decarboxylase eine spezifische Aktivität bezüglich der Phenylacetylcarbinolbildung von > 1U/mg. Ziel der Erfindung ist, eine Pyruvat-decarboxylase mit verbesserter Synthesekapazität bezüglich der Bildung von (R)-(-)-Phenylacetylcarbinol zu erhalten. Das zu diesem Zweck entwickelte erfindungsgemäße Verfahren zeichnet sich dadurch aus, daß man einen Produzenten-Organismus mit einem für Pyruvat-decarboxylase kodierenden Gen aus Zymomonas mobilis verwendet, in dessen DNA-Sequenz das für den Tryptophanrest kodierende Kodon TGG an der Position 1174-1176 durch ein Kodon ersetzt ist, das für einen Aminosäurerest mit verminderter Raumerfüllung kodiert.
PCT/DE1996/000928 1995-05-26 1996-05-22 Verfahren zur gewinnung von acyloinen, dafür geeignete pyruvat-decarboxylase sowie deren herstellung und dna-sequenz des für diese kodierenden pdc-gens Ceased WO1996037620A2 (de)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP96919594A EP0828841A2 (de) 1995-05-26 1996-05-22 Verfahren zur gewinnung von acyloinen, dafür geeignete pyruvat-decarboxylase sowie deren herstellung und dna-sequenz des für diese kodierenden pdc-gens
AU58102/96A AU714414B2 (en) 1995-05-26 1996-05-22 Process for obtaining acyloins, pyruvate decarboxylases suitable therefor and their production and DNA sequences of the PDC gene coding them
BR9608798A BR9608798A (pt) 1995-05-26 1996-05-22 Processo para obter aciloínas piruvato descarboxilases adequadas para as mesmas tal fim e sua produção e sequências de dna do gene de pdc que as codificam
JP8535270A JPH11505710A (ja) 1995-05-26 1996-05-22 アシロインの生成方法、これに適するピルビン酸−デカルボキシラーゼ並びにその産生方法及びこの酵素をコードするｐｄｃ−遺伝子のｄｎａ−配列

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19518809 1995-05-26
DE19518809.8 1995-06-29
DE19523269A DE19523269C2 (de) 1995-05-26 1995-06-29 Verfahren zur Gewinnung von Acyloinen, dafür geeignete Pyruvat-decarboxylase sowie deren Herstellung und DNA-Sequenz des für diese kodierenden PDC-Gens
DE19523269.0 1995-06-29

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US08/976,852 Continuation-In-Part US6004789A (en) 1995-05-26 1997-11-24 Process for obtaining acyloins, pyruvate decarboxylases suitable therefor and their production and DNA sequence of the PDC gene coding them

Publications (2)

Publication Number Publication Date
WO1996037620A2 WO1996037620A2 (de) 1996-11-28
WO1996037620A3 true WO1996037620A3 (de) 1997-02-06

Family

ID=26015375

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE1996/000928 Ceased WO1996037620A2 (de) 1995-05-26 1996-05-22 Verfahren zur gewinnung von acyloinen, dafür geeignete pyruvat-decarboxylase sowie deren herstellung und dna-sequenz des für diese kodierenden pdc-gens

Country Status (12)

Country Link
US (1) US6004789A (de)
EP (1) EP0828841A2 (de)
JP (1) JPH11505710A (de)
KR (1) KR19990021965A (de)
CN (1) CN1192244A (de)
AU (1) AU714414B2 (de)
BR (1) BR9608798A (de)
CA (1) CA2222493A1 (de)
CZ (1) CZ287619B6 (de)
DE (1) DE19523269C2 (de)
IN (2) IN186507B (de)
WO (1) WO1996037620A2 (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19736104A1 (de) * 1997-08-20 1999-02-25 Basf Ag Verfahren zur Herstellung von enantiomerenreinen Phenylacetylcarbinolen aus Acetaldchyd und Benzaldehyd in Gegenwart von Pyruvatdecarboxylase aus Zymomonas
DE19918935A1 (de) * 1999-04-27 2000-11-02 Forschungszentrum Juelich Gmbh Stereoselektive Synthese von 2-Hydroxyketonen
CN1678735A (zh) * 2001-05-04 2005-10-05 佛罗里达大学研究基金会有限公司 来源于细菌的丙酮酸脱羧酶(pdc)基因的克隆和测序及其用途
DE10142467A1 (de) * 2001-08-31 2003-03-20 Basf Ag Neue Pyruvatdecarboxylase, ihre Herstellung und Verwendung
DE10142574A1 (de) * 2001-09-01 2003-03-20 Basf Ag Verfahren zur Herstellung von R-Phenylacetylcarbinol durch ein enzymatisches verfahren in einem Zweiphasensystem
IL147823A (en) 2002-01-24 2008-06-05 Univ Ben Gurion Process for the preparation of alpha-hydroxy aromatic chiral ketones using acetohydroxyacide synthase
DE10313971A1 (de) * 2003-03-27 2004-10-21 Degussa Ag Gekoppeltes cofaktorabhängiges enzymatisches Reaktionssystem
DE102014013644A1 (de) * 2014-09-16 2016-03-17 Forschungszentrum Jülich GmbH Lyase und für die Lyase kodierende DNA, die DNA enthaltende Vektoren, sowie Verfahren zur asymmetrischen Synthese von (S)-Phenylacetylcarbinol
CN107630049B (zh) * 2017-04-01 2018-09-21 武汉茵茂特生物技术有限公司 麻黄碱的生物制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE548459C (de) * 1930-04-09 1932-04-13 Gustav Hildebrandt Dr Verfahren zur Herstellung von 1-1-Phenyl-2-methylaminopropan-1-ol

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BRUHN H ET AL: "The replacement of Trp392 by alanine influences the decarboxylase/carboligase activity and stability of pyruvate decarboxylase from Zymomonas mobilis.", EUR J BIOCHEM, DEC 1 1995, 234 (2) P650-5, GERMANY, XP000607025 *
CANDY JM ET AL: "Investigation of the cofactor-binding site of Zymomonas mobilis pyruvate decarboxylase by site-directed mutagenesis.", BIOCHEM J, MAY 15 1994, 300 ( PT 1) P7-13, ENGLAND, XP000607055 *
CROUT DHG ET AL: "Application of hydrolytic and decarboxylating enzymes in biotransformations", BIOCATALYSIS, vol. 9, 1994, pages 1 - 30, XP000610933 *
DIEFENBACH RJ ET AL: "Effects of substitution of aspartate-440 and tryptophan-487 in the thiamin diphophate binding region of pyruvate decarboxylase from Zymomonas mobilis", FEBS LETTERS, vol. 296, 1992, AMSTERDAM NL, pages 95 - 98, XP000608119 *
POHL M ET AL: "Reversible dissociation and unfolding of pyruvate decarboxylase from Zymomonas mobilis.", EUR J BIOCHEM, SEP 1 1994, 224 (2) P651-61, GERMANY, XP000607136 *

Also Published As

Publication number Publication date
CN1192244A (zh) 1998-09-02
AU5810296A (en) 1996-12-11
CZ369197A3 (cs) 1998-02-18
IN186507B (de) 2001-09-22
DE19523269A1 (de) 1996-11-28
KR19990021965A (ko) 1999-03-25
CA2222493A1 (en) 1996-11-28
US6004789A (en) 1999-12-21
DE19523269C2 (de) 2000-05-31
CZ287619B6 (en) 2001-01-17
BR9608798A (pt) 1999-02-17
WO1996037620A2 (de) 1996-11-28
IN189539B (de) 2003-03-22
AU714414B2 (en) 2000-01-06
JPH11505710A (ja) 1999-05-25
EP0828841A2 (de) 1998-03-18

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