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  • 1
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    A Microbiological approach to kinetic resolution of racemic estra-4,9-dienes (1985)
    Elsevier
    Details
    Publication Date: 1985-01-01
    Print ISSN: 0040-4039
    Electronic ISSN: 1873-3581
    Topics: Chemistry and Pharmacology
    Published by Elsevier
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    PAPER CURRENT
  • 2
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlungen nichtsteroider Strukturen, V. Mikrobiologische Reaktionen von substituierten 1-Äthyl-4-oxo-1,4-dihydrochinolin-3-carbonsäuren (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 2636-2642 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbiological Transformations of Nonsteroidal Structures, V. Microbiological Reactions of Substituted 1-Ethyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acids1-Ethyl-7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (1) is transformed to the methyl ester by Streptomyces surinam. Penicillium adametzi hydroxylates the substrate at the 7-methyl substituent, whereas 1 -ethyl-8-methoxy-5-methyl-4-oxo- 1,4-dihydroquinoline-3-carboxylic acid (4) is hydrolyzed to the free phenol by the same fungi. l-Ethyl-4-oxo-1,4,6,7,8,9-hexahydrobenzo[g]quinolinc-3-carboxylic acid (6) is hydroxylated in 7 - and 8-position by Penicillium adametzi, in 6- and 7- (or 8-) position by Streptomyces achromogenes and in 6-position by Sporotrichum sulfurescens. 5-Ethyl-8-oxo-2,3,5,8-tetrahydrofuro[2,3-g]quinoline-7-carboxylic acid (10) undergoes only a hydrolytic cleavage of the dihydrofuranering.
    Notes: 1-Äthyl-7-methyl-4-oxo-1,4-dihydrochinolin-3-carbonsäure (1) wird durch Streptomyces surinam in den Methylester umgewandelt. Penicillium adametzi hydroxyliert das Substrat am 7-Methylsubstituenten, während bei der 1 -Äthyl-8-methoxy-5-methyl-4-oxo- 1, 4-dihydrochinolin-3-carbonsäure (4) mit dem gleichen Pilz nur eine Phenolätherspaltung eintritt. 1-Äthyl-4-oxo-l,4,6,7,8,9-hexahydrobenzo[g]chinolin-3-carbonsäure (6) wird von Penicillium adametzi in 7- und 8-, von Streptomyces achromogenes in 7-(oder 8-) und 6- sowie von Spororrichum sulfurescens in 6-Stellung hydroxyliert. 5-Äthyl-8-oxo-2,3,5,8-tetrahydrofuro[2,3-g]-chinolin-7-carbonsäure (10) zeigt nur eine hydrolytische Spaltung des Dihydrofuranringes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060827
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  • 3
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlung von Steroiden, XVI. Synthese von 11β, 21-Dihydroxy-6, 16α-dimethyl-1,4,6,-pregnatrien-3,20-dion und dessen 11-Ketoverbindung (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 979-989 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbial Transformations of Steroids XVI. Synthesis of 11β,21-Dihydroxy-6, 16α-dimethyl-1,4,6-pregnatriene-3,20-dione and of its 11-Keto Compound21-Acetoxy-5α,6α-epoxy-3β-hydroxy-6β16α-dimethyl-20-pregnanone (3a), prepared from 3β-hydroxy-6, 16α-dimethyl-5-pregnen-20-one (1) by epoxidation and chemical introduction of the 21-acetoxy group, was oxidized to 6α,21-dihydroxy-6β,16α-dimethyl-4-pregnene-3,20-dione (4) by Flavobacterium dehydrogenans and dehydrated to the 3-keto-4,6-diene 5. The 11β-hydroxy group was introduced by Curvularia lunata to give 6, and the 11α-hydroxy group by Aspergillus ochraceus to yield 8. Both compounds were dehydrogenated with Bacillus lentus to from 7 and 9. The 11α-hydroxy compound 9 was selectively acetylated to 10, which was oxidize to 11. This on saponification yielded 12.
    Notes: 21-Acetoxy-5α,6α-epoxy-3β-hydroxy-6β,16α-dimethyl-20-pregnanon (3a), dargestellt aus 3β-Hydroxy-6, 16α-dimethyl-5-pregnen-20-on (1) durch Epoxidierung und 21-Acetoxylierung, wurde mit Flavobacterium dehydrogenans zu 6α,21-Dihydroxy-6β, 16α, -dimethyl-4-pregnen-3,20-dion (4) oxidiert und zu 21-Hydroxy-6, 16α-dimethyl-4,6-pregnadien-3,20-dion (5) dehydratisiert. Mit Curvularia lunata wurde die 11β-Hydroxygruppe eingeführt zu 6, während Aspergillus ochraceus die entsprechende 11α-Hydroxyverbindung 8 ergab. Beide Verbindungen wurden mit Bacillus lentus zu 7 bzw. 9 dehydriert. Die 11α-Hydroxyverbindung 9 wurde nach selektiver Acetylierung der 21-Hydroxygruppe zu 10 zum 11-Keton 11 oxidiert, dessen Verseifung 12 ergab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791120320
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  • 4
    Electronic Resource
    Electronic Resource
    Mikrobiologische 11β-Hydroxylierung von 3β-Hydroxy-5α.6α-epoxy-steroiden (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 205-209 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbiological 11β-Hydroxylation of 3β-Hydroxy-5α.6α-epoxysteroidsSome 3β-Hydroxy-5α,6α-epoxysteroids are hydroxylated specifically in 11β-position without formation of by-products by the fungus Curvularia lunata.
    Notes: Eine Reihe von 3β-Hydroxy-5α.6α-epoxy-steroiden wird mit dem Pilz Curvularia lunata ohne Bildung von Nebenprodukten spezifisch in 11β-Stellung hydroxyliert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040125
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  • 5
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlungen nichtsteroider Strukturen, IV. Mikrobiologische Spaltung eines Nitrofuran-Derivates (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 1303-1308 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbiological Transformations of Nonsteroidal Structures, IV. Microbiological Cleavage of a Nitrofurane Derivative5-Methoxy-2-(5-nitrofurfurylidene)-1-indanone (1) is opened by several microorganisms reductively to yield 2-(4-cyano-2-oxobutyl)-5-methoxy-1-indanone (2). In part an additional cleavage of the phenolic methoxy group occurs with formation of 2-(4-cyano-2-oxobutyl)-5-hydroxy-1-indanone (3).
    Notes: 5-Methoxy-2-(5-nitrofurfuryliden)-1-indanon (1) wird von mehreren Mikroorganismen reduktiv zu 2-(4-Cyan-2-oxobutyl)-5-methoxy-1-indanon (2) geöffnet. Teilweise erfolgt zusätzlich eine Spaltung der phenolischen Methyläthergruppe zu 2-(4-Cyan-2-oxobutyl)-5-hydroxy-1-indanon (3).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060427
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  • 6
    Electronic Resource
    Electronic Resource
    Mikrobiologische Hydroxylierung von 3β-Hydroxy-5α.6α-epoxy-5α-pregnanonen-(20) mit Folgereaktionen (1972)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 105 (1972), S. 658-672 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbiological Hydroxylation of 5α.6α-Epoxy-3β-hydroxy-5α-pregnane-20-ones with further TransformationsThe fungus Curvularia lunata transforms in prolongated incubation time 5α.6α; 16α.17α-diepoxy-3β-hydroxy-5α-pregnane-20-one (1) to the 5β-H-6-ketone 3 and 4 through the primarily formed 11β-hydroxy-structure 2. 5α.6α-Epoxy-3β-hydroxy-5α-pregnane-20-one (6) is oxidized to 14α- or 17α-hydroxy-11-ketones (8-10, 12). During this reaction a change of the substitution pattern of the rings A and B is sometimes observed. The corresponding 16α-methyl-substituted substrate 14 is transformed through some intermediates to the stable product 5α.6α-epoxy-3β.15β-dihydroxy-16α-methyl-5α-pregnane-11.20-dione (18). The constitutions of the isolated compounds were elucidated by n.m.r., i.r., mass spectroscopic, and c.d. investigations.
    Notes: Der Pilz Curvularia lunata wandelt 3β-Hydroxy-5α.6α; 16α.17α-diepoxy-5α-pregnanon-(20) (1) bei verlängerter Inkubationszeit über die primär entstehende 11β-Hydroxystruktur 2 in die 5β-H-6-Ketone 3 und 4 um. 3β-Hydroxy-5α.6α-epoxy-5α-pregnanon-(20) (6) wird zu 14α-oder 17α-Hydroxy-11-ketonen (8-10, 12) oxydiert, wobei gleichzeitig noch eine Änderung des Substitutionsmusters am A- und B-Ring eintreten kann, während die entsprechende 16α-Methylverbindung 14 über verschiedene Zwischenstufen zum stabilen Endprodukt 3β.15β-Di-hydroxy-5α.6α-epoxy-16α-methyl-5α-pregnandion-(11.20) (18) transformiert wird. Die Konstitutionen der isolierten Verbindungen wurden durch NMR-, IR-, MS- und CD-Untersuchungen gesichert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19721050232
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