DE19929577A1 - Yeast alpha-oxidation enzymes, used to degrade organic compounds by one carbon atom, used to convert 5-hydroxydecanoic acid to gamma-nonalactone - Google Patents

Yeast alpha-oxidation enzymes, used to degrade organic compounds by one carbon atom, used to convert 5-hydroxydecanoic acid to gamma-nonalactone

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Publication number
DE19929577A1
DE19929577A1 DE1999129577 DE19929577A DE19929577A1 DE 19929577 A1 DE19929577 A1 DE 19929577A1 DE 1999129577 DE1999129577 DE 1999129577 DE 19929577 A DE19929577 A DE 19929577A DE 19929577 A1 DE19929577 A1 DE 19929577A1
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Germany
Prior art keywords
organic compounds
carbon atom
oxidation
nonalactone
gamma
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.)
Withdrawn
Application number
DE1999129577
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German (de)
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.)
GARBE LEIF ALEXANDER
Original Assignee
GARBE LEIF ALEXANDER
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.)
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Application filed by GARBE LEIF ALEXANDER filed Critical GARBE LEIF ALEXANDER
Priority to DE1999129577 priority Critical patent/DE19929577A1/en
Publication of DE19929577A1 publication Critical patent/DE19929577A1/en
Withdrawn legal-status Critical Current

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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
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • 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
    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • 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
    • C12P7/42—Hydroxy-carboxylic acids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Using alpha -oxidation enzymes of yeasts Saccharomyces cerevisiae, Candida lipolytica, Candida albicans and Candida tropicalis to cleave organic compounds to form products with one less carbon atom and release formic acid, to effect enantiomeric or diastereomeric resolution of chiral compounds, to produce hydroxylated organic compounds, and to produce chiral psi - and delta -lactones, is new.

Description

In tierischen Zellen und Pflanzen sind α-Oxidationen weit verbreitet. Dabei wird in Nachbarstellung (α-) zu einer Carboxylgruppe hydroxyliert, zum Keton oxidiert und durch eine Formiat-Lyase Ameisensäure abgespalten. Völlig überraschend fanden wir, daß diese Reaktion auch in Hefen abläuft, was bisher nicht bekannt war. Inkubationsexperimente mit aufgereinigten Hefe-Peroxysomen zeigten eindeutig, daß Hefen in der Lage sind z. B. 3-Methylpentansäure, 3-Hydroxyoctansäure, 5- Hydroxyoctansäure, 3,4-Dihydroxydecansäure, 5,6-Dihydroxydodecansäure, 7,8- Dihydroxytetradecansäure und 2-Hydroxyoctansäure sowohl um ein Kohlenstoff-Atom (Carboxyl-Gruppe) zu verkürzen, als auch Terminal- bzw. Subterminal zu hydroxyliernen und oxidieren. Diese α-Oxidationsreaktion vermag zwischen Enatiomeren zu differenzieren und kann mehrfach nacheinander ablaufen.Α-Oxidations are widespread in animal cells and plants. Thereby in Neighboring position (α-) hydroxylated to a carboxyl group, oxidized to the ketone and by a formate lyase cleaved formic acid. We found it completely surprising that this reaction also takes place in yeasts, which so far has not was known. Incubation experiments with purified yeast peroxysomes showed clearly that yeasts are capable of e.g. B. 3-methylpentanoic acid, 3-hydroxyoctanoic acid, 5- Hydroxyoctanoic acid, 3,4-dihydroxydecanoic acid, 5,6-dihydroxydodecanoic acid, 7,8- Dihydroxytetradecanoic acid and 2-hydroxyoctanoic acid are both around one carbon atom (Carboxyl group) to shorten, as well as to hydroxylate terminal or subterminal and oxidize. This α-oxidation reaction is able to differentiate between enantiomers and can run several times in succession.

Claims (3)

1. Wir beanspruchen die Nutzung der α-Oxidation in Hefen (Saccharomyces cerevisiae, Candida lipolytica, Candida albicans, Candida tropicalis) zur Gewinnung von Kohlenstoff-kettenverkürzten organischen Molekülen sowie der entstehenden biogenen Ameisensäure und zur Enantiomeren- bzw. Diastereomerendifferenzierung chiraler Verbindungen.1. We claim the use of α-oxidation in yeast (Saccharomyces cerevisiae, Candida lipolytica, Candida albicans, Candida tropicalis) for the production of Carbon chain shortened organic molecules and the resulting biogenic Formic acid and chiral for enantiomer or diastereomer differentiation Links. 2. Gewinnung von hydoxylierten organischen Verbindungen durch die in Saccharomyces cerevisiae beschrieben Enzyme der α-Oxidation.2. Obtaining hydrogenated organic compounds by the in Saccharomyces cerevisiae described enzymes of α-oxidation. 3. Gewinnung von chiralen γ- und δ-Lactonen (cyclische Ester 5- und 6-Ring) durch die Enzyme der α-Oxidation in Saccharomyces cerevisiae durch ein- oder mehrfache C1-Kettenverkürzung.3. Obtaining chiral γ- and δ-lactones (cyclic esters 5- and 6-ring) by the enzymes of α-oxidation in Saccharomyces cerevisiae by single or multiple C 1 chain shortening.
DE1999129577 1999-06-22 1999-06-22 Yeast alpha-oxidation enzymes, used to degrade organic compounds by one carbon atom, used to convert 5-hydroxydecanoic acid to gamma-nonalactone Withdrawn DE19929577A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE1999129577 DE19929577A1 (en) 1999-06-22 1999-06-22 Yeast alpha-oxidation enzymes, used to degrade organic compounds by one carbon atom, used to convert 5-hydroxydecanoic acid to gamma-nonalactone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1999129577 DE19929577A1 (en) 1999-06-22 1999-06-22 Yeast alpha-oxidation enzymes, used to degrade organic compounds by one carbon atom, used to convert 5-hydroxydecanoic acid to gamma-nonalactone

Publications (1)

Publication Number Publication Date
DE19929577A1 true DE19929577A1 (en) 2000-12-28

Family

ID=7912821

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1999129577 Withdrawn DE19929577A1 (en) 1999-06-22 1999-06-22 Yeast alpha-oxidation enzymes, used to degrade organic compounds by one carbon atom, used to convert 5-hydroxydecanoic acid to gamma-nonalactone

Country Status (1)

Country Link
DE (1) DE19929577A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2595261A (en) * 2020-05-19 2021-11-24 Tallinn Univ Of Technology Enzyme-catalytic method for the direct stereoselective synthesis of gamma-(acetyloxy) carboxylic acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2595261A (en) * 2020-05-19 2021-11-24 Tallinn Univ Of Technology Enzyme-catalytic method for the direct stereoselective synthesis of gamma-(acetyloxy) carboxylic acids

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