Preparation of 4-(4'-hydroxyanilino)-5-anilinophthalimide and 4,5-bis-(4'-hydroxyanilino)-phthalimide by microbial hydroxylation
A microbial screening indicated that two fungal strains, Beauveria bassiana DSM 1344=ATCC 7159 and Cunninghamella elegans DSM 1908=ATCC 9245, as well as four bacterial strains belonging to the genus Streptomyces were able to hydroxylate 4,5-dianilinophthalimide (DAPH, CGP52411) to 4-(4′-hydroxyanili...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 1999-01, Vol.63 (8), p.1497-1500 |
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| container_title | Bioscience, biotechnology, and biochemistry |
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| creator | Weidner, S. (Novartis Pharma AG, Basel (Switzerland)) Goeke, K Trinks, U Traxler, P Ucci-Stoll, K Ghisalba, O |
| description | A microbial screening indicated that two fungal strains, Beauveria bassiana DSM 1344=ATCC 7159 and Cunninghamella elegans DSM 1908=ATCC 9245, as well as four bacterial strains belonging to the genus Streptomyces were able to hydroxylate 4,5-dianilinophthalimide (DAPH, CGP52411) to 4-(4′-hydroxyanilino)-5-anilinophthalimide. Cunninghamella elegans DSM 1908 turned out to be the most active biocatalyst and was also able to form the dihydroxy derivative, 4,5-bis(4′-hydroxyanilino)phthalimide. The reaction for the monohydroxylated biotransformation product was carried out on a preparative scale, and the culture conditions for the formation of 4-(4′-hydroxy- anilino)-5-anilinophthalimide with this strain were op-timized. |
| doi_str_mv | 10.1271/bbb.63.1497 |
| format | Article |
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(Novartis Pharma AG, Basel (Switzerland)) ; Goeke, K ; Trinks, U ; Traxler, P ; Ucci-Stoll, K ; Ghisalba, O</creator><creatorcontrib>Weidner, S. (Novartis Pharma AG, Basel (Switzerland)) ; Goeke, K ; Trinks, U ; Traxler, P ; Ucci-Stoll, K ; Ghisalba, O</creatorcontrib><description>A microbial screening indicated that two fungal strains, Beauveria bassiana DSM 1344=ATCC 7159 and Cunninghamella elegans DSM 1908=ATCC 9245, as well as four bacterial strains belonging to the genus Streptomyces were able to hydroxylate 4,5-dianilinophthalimide (DAPH, CGP52411) to 4-(4′-hydroxyanilino)-5-anilinophthalimide. Cunninghamella elegans DSM 1908 turned out to be the most active biocatalyst and was also able to form the dihydroxy derivative, 4,5-bis(4′-hydroxyanilino)phthalimide. The reaction for the monohydroxylated biotransformation product was carried out on a preparative scale, and the culture conditions for the formation of 4-(4′-hydroxy- anilino)-5-anilinophthalimide with this strain were op-timized.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1271/bbb.63.1497</identifier><identifier>PMID: 27389513</identifier><language>eng</language><publisher>Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry</publisher><subject>4,5-bis-(4′-hydroxyanilino)-phthalimide ; 4-(4′-hydroxyanilino)-5-anilinophthalimide ; BEAUVERIA BASSIANA ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; CUNNINGHAMELLA ; Fundamental and applied biological sciences. Psychology ; HIDROXILACION ; HYDROXYLATION ; Methods. Procedures. 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(Novartis Pharma AG, Basel (Switzerland))</creatorcontrib><creatorcontrib>Goeke, K</creatorcontrib><creatorcontrib>Trinks, U</creatorcontrib><creatorcontrib>Traxler, P</creatorcontrib><creatorcontrib>Ucci-Stoll, K</creatorcontrib><creatorcontrib>Ghisalba, O</creatorcontrib><title>Preparation of 4-(4'-hydroxyanilino)-5-anilinophthalimide and 4,5-bis-(4'-hydroxyanilino)-phthalimide by microbial hydroxylation</title><title>Bioscience, biotechnology, and biochemistry</title><addtitle>Biosci Biotechnol Biochem</addtitle><description>A microbial screening indicated that two fungal strains, Beauveria bassiana DSM 1344=ATCC 7159 and Cunninghamella elegans DSM 1908=ATCC 9245, as well as four bacterial strains belonging to the genus Streptomyces were able to hydroxylate 4,5-dianilinophthalimide (DAPH, CGP52411) to 4-(4′-hydroxyanilino)-5-anilinophthalimide. Cunninghamella elegans DSM 1908 turned out to be the most active biocatalyst and was also able to form the dihydroxy derivative, 4,5-bis(4′-hydroxyanilino)phthalimide. The reaction for the monohydroxylated biotransformation product was carried out on a preparative scale, and the culture conditions for the formation of 4-(4′-hydroxy- anilino)-5-anilinophthalimide with this strain were op-timized.</description><subject>4,5-bis-(4′-hydroxyanilino)-phthalimide</subject><subject>4-(4′-hydroxyanilino)-5-anilinophthalimide</subject><subject>BEAUVERIA BASSIANA</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>CUNNINGHAMELLA</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>HIDROXILACION</subject><subject>HYDROXYLATION</subject><subject>Methods. Procedures. 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| source | Oxford University Press Journals All Titles (1996-Current); J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Open Access Titles of Japan; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 4,5-bis-(4′-hydroxyanilino)-phthalimide 4-(4′-hydroxyanilino)-5-anilinophthalimide BEAUVERIA BASSIANA Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology CUNNINGHAMELLA Fundamental and applied biological sciences. Psychology HIDROXILACION HYDROXYLATION Methods. Procedures. Technologies microbial hydroxylation PTK-inhibitors STREPTOMYCES |
| title | Preparation of 4-(4'-hydroxyanilino)-5-anilinophthalimide and 4,5-bis-(4'-hydroxyanilino)-phthalimide by microbial hydroxylation |
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