Metabolism of chiral ionylideneacetic acids on the abscisic acid biosynthetic pathway in Cercospora
A Chiralcel OJ column was used to determine the absolute configuration of naturally occurring α-ionylideneacetic acid from Cercospora rosicola and γ-ionylideneacetic acid from C. cruenta as (R) enantiomers in accordance with their biosynthetic product, (S)-ABA. Both enantiomers of [1, 2- 13 C 2 ]-α...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2000-12, Vol.64 (12), p.2644-2650 |
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| container_title | Bioscience, biotechnology, and biochemistry |
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| creator | Yamamoto, H. (Niigata Univ. (Japan). Faculty of Agriculture) Inomata, M Tsuchiya, S Nakamura, M Oritani, T |
| description | A Chiralcel OJ column was used to determine the absolute configuration of naturally occurring α-ionylideneacetic acid from Cercospora rosicola and γ-ionylideneacetic acid from C. cruenta as (R) enantiomers in accordance with their biosynthetic product, (S)-ABA. Both enantiomers of [1, 2-
13
C
2
]-α and γ-ionylideneacetic acids were prepared and fed to C. rosicola and C. cruenta. Six combinations of feeding experiments comparatively and unequivocally demonstrated stereoselectivity in the biosynthetic conversions, including stepwise hydroxylation at C-1′ and 4′. Enzymatic isomerization from the γ to α-intermediate was suggested not to be involved in ABA biosynthesis in C. rosicola. |
| doi_str_mv | 10.1271/bbb.64.2644 |
| format | Article |
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13
C
2
]-α and γ-ionylideneacetic acids were prepared and fed to C. rosicola and C. cruenta. Six combinations of feeding experiments comparatively and unequivocally demonstrated stereoselectivity in the biosynthetic conversions, including stepwise hydroxylation at C-1′ and 4′. Enzymatic isomerization from the γ to α-intermediate was suggested not to be involved in ABA biosynthesis in C. rosicola.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1271/bbb.64.2644</identifier><identifier>PMID: 11210128</identifier><language>eng</language><publisher>Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry</publisher><subject>ABA ; abscisic acid ; Abscisic Acid - analogs & derivatives ; Abscisic Acid - biosynthesis ; Abscisic Acid - chemistry ; Abscisic Acid - metabolism ; Analytical, structural and metabolic biochemistry ; BIOCHEMICAL PATHWAYS ; Biological and medical sciences ; BIOSYNTHESIS ; CERCOSPORA ; Cercospora cruenta ; Cercospora rosicola ; Fundamental and applied biological sciences. Psychology ; Fungal plant pathogens ; Glutamic Acid - metabolism ; Growth regulators ; Metabolism ; Mitosporic Fungi - metabolism ; Other biological molecules ; Phosphates - metabolism ; Phytopathology. Animal pests. Plant and forest protection ; Plant physiology and development ; Stereoisomerism ; Substrate Specificity ; Systematics. Morphology. Development cycle. Physiology ; Terpenes, steroids. Hormones ; Thiamine - metabolism ; α-ionylideneacetic acid ; γ-ionylideneacetic acid</subject><ispartof>Bioscience, biotechnology, and biochemistry, 2000-12, Vol.64 (12), p.2644-2650</ispartof><rights>2000 by Japan Society for Bioscience, Biotechnology, and Agrochemistry 2000</rights><rights>2001 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2000</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c536t-b9fb2efd1dc87debd3e3bdaf0e162f7ef149817770c25db6a5f602bc265e795a3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=926972$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11210128$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yamamoto, H. (Niigata Univ. (Japan). Faculty of Agriculture)</creatorcontrib><creatorcontrib>Inomata, M</creatorcontrib><creatorcontrib>Tsuchiya, S</creatorcontrib><creatorcontrib>Nakamura, M</creatorcontrib><creatorcontrib>Oritani, T</creatorcontrib><title>Metabolism of chiral ionylideneacetic acids on the abscisic acid biosynthetic pathway in Cercospora</title><title>Bioscience, biotechnology, and biochemistry</title><addtitle>Biosci Biotechnol Biochem</addtitle><description>A Chiralcel OJ column was used to determine the absolute configuration of naturally occurring α-ionylideneacetic acid from Cercospora rosicola and γ-ionylideneacetic acid from C. cruenta as (R) enantiomers in accordance with their biosynthetic product, (S)-ABA. Both enantiomers of [1, 2-
13
C
2
]-α and γ-ionylideneacetic acids were prepared and fed to C. rosicola and C. cruenta. Six combinations of feeding experiments comparatively and unequivocally demonstrated stereoselectivity in the biosynthetic conversions, including stepwise hydroxylation at C-1′ and 4′. Enzymatic isomerization from the γ to α-intermediate was suggested not to be involved in ABA biosynthesis in C. rosicola.</description><subject>ABA</subject><subject>abscisic acid</subject><subject>Abscisic Acid - analogs & derivatives</subject><subject>Abscisic Acid - biosynthesis</subject><subject>Abscisic Acid - chemistry</subject><subject>Abscisic Acid - metabolism</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>BIOCHEMICAL PATHWAYS</subject><subject>Biological and medical sciences</subject><subject>BIOSYNTHESIS</subject><subject>CERCOSPORA</subject><subject>Cercospora cruenta</subject><subject>Cercospora rosicola</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fungal plant pathogens</subject><subject>Glutamic Acid - metabolism</subject><subject>Growth regulators</subject><subject>Metabolism</subject><subject>Mitosporic Fungi - metabolism</subject><subject>Other biological molecules</subject><subject>Phosphates - metabolism</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Plant physiology and development</subject><subject>Stereoisomerism</subject><subject>Substrate Specificity</subject><subject>Systematics. Morphology. Development cycle. Physiology</subject><subject>Terpenes, steroids. Hormones</subject><subject>Thiamine - metabolism</subject><subject>α-ionylideneacetic acid</subject><subject>γ-ionylideneacetic acid</subject><issn>0916-8451</issn><issn>1347-6947</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0NtrFDEUBvAgFrutPvmsBARfZNbcJpl5LIvWSkUf9Dmc3NyUmcmazFLmv2-WXS8UnwIfv3NO-BB6ScmaMkXfG2PWUqyZFOIJWlEuVCN7oZ6iFempbDrR0nN0UcodITVo6TN0TimjhLJuhewXP4NJQywjTgHbbcww4JimZYjOTx6sn6PFYKMrOE143noMpthYTik2MZVlqvnB7WDe3sOC44Q3PttUdinDc3QWYCj-xem9RD8-fvi--dTcfr2-2VzdNrblcm5MHwzzwVFnO-W8cdxz4yAQTyULygcq-o4qpYhlrTMS2iAJM5bJ1qu-BX6J3h737nL6tfdl1mMs1g8DTD7ti1asbaVgvMI3j-Bd2uep_k1TIXrBJe1UVe-OyuZUSvZB73IcIS-aEn1oXtfmtRT60HzVr08792b07q89Vf3PUSgWhpBhqi3-cT2TvWJVyaOKU0h5hPuUB6dnWIaUf4_w_99_dRwMkDT8zNV9_sYIoYTw2ht_AH0Xp5Q</recordid><startdate>20001201</startdate><enddate>20001201</enddate><creator>Yamamoto, H. (Niigata Univ. (Japan). Faculty of Agriculture)</creator><creator>Inomata, M</creator><creator>Tsuchiya, S</creator><creator>Nakamura, M</creator><creator>Oritani, T</creator><general>Japan Society for Bioscience, Biotechnology, and Agrochemistry</general><general>Japan Society for Bioscience Biotechnology and Agrochemistry</general><general>Oxford University Press</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20001201</creationdate><title>Metabolism of chiral ionylideneacetic acids on the abscisic acid biosynthetic pathway in Cercospora</title><author>Yamamoto, H. (Niigata Univ. (Japan). Faculty of Agriculture) ; Inomata, M ; Tsuchiya, S ; Nakamura, M ; Oritani, T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c536t-b9fb2efd1dc87debd3e3bdaf0e162f7ef149817770c25db6a5f602bc265e795a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>ABA</topic><topic>abscisic acid</topic><topic>Abscisic Acid - analogs & derivatives</topic><topic>Abscisic Acid - biosynthesis</topic><topic>Abscisic Acid - chemistry</topic><topic>Abscisic Acid - metabolism</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>BIOCHEMICAL PATHWAYS</topic><topic>Biological and medical sciences</topic><topic>BIOSYNTHESIS</topic><topic>CERCOSPORA</topic><topic>Cercospora cruenta</topic><topic>Cercospora rosicola</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fungal plant pathogens</topic><topic>Glutamic Acid - metabolism</topic><topic>Growth regulators</topic><topic>Metabolism</topic><topic>Mitosporic Fungi - metabolism</topic><topic>Other biological molecules</topic><topic>Phosphates - metabolism</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>Plant physiology and development</topic><topic>Stereoisomerism</topic><topic>Substrate Specificity</topic><topic>Systematics. Morphology. Development cycle. Physiology</topic><topic>Terpenes, steroids. Hormones</topic><topic>Thiamine - metabolism</topic><topic>α-ionylideneacetic acid</topic><topic>γ-ionylideneacetic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamamoto, H. (Niigata Univ. (Japan). Faculty of Agriculture)</creatorcontrib><creatorcontrib>Inomata, M</creatorcontrib><creatorcontrib>Tsuchiya, S</creatorcontrib><creatorcontrib>Nakamura, M</creatorcontrib><creatorcontrib>Oritani, T</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioscience, biotechnology, and biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yamamoto, H. (Niigata Univ. (Japan). Faculty of Agriculture)</au><au>Inomata, M</au><au>Tsuchiya, S</au><au>Nakamura, M</au><au>Oritani, T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metabolism of chiral ionylideneacetic acids on the abscisic acid biosynthetic pathway in Cercospora</atitle><jtitle>Bioscience, biotechnology, and biochemistry</jtitle><addtitle>Biosci Biotechnol Biochem</addtitle><date>2000-12-01</date><risdate>2000</risdate><volume>64</volume><issue>12</issue><spage>2644</spage><epage>2650</epage><pages>2644-2650</pages><issn>0916-8451</issn><eissn>1347-6947</eissn><abstract>A Chiralcel OJ column was used to determine the absolute configuration of naturally occurring α-ionylideneacetic acid from Cercospora rosicola and γ-ionylideneacetic acid from C. cruenta as (R) enantiomers in accordance with their biosynthetic product, (S)-ABA. Both enantiomers of [1, 2-
13
C
2
]-α and γ-ionylideneacetic acids were prepared and fed to C. rosicola and C. cruenta. Six combinations of feeding experiments comparatively and unequivocally demonstrated stereoselectivity in the biosynthetic conversions, including stepwise hydroxylation at C-1′ and 4′. Enzymatic isomerization from the γ to α-intermediate was suggested not to be involved in ABA biosynthesis in C. rosicola.</abstract><cop>Tokyo</cop><pub>Japan Society for Bioscience, Biotechnology, and Agrochemistry</pub><pmid>11210128</pmid><doi>10.1271/bbb.64.2644</doi><tpages>7</tpages></addata></record> |
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| ispartof | Bioscience, biotechnology, and biochemistry, 2000-12, Vol.64 (12), p.2644-2650 |
| issn | 0916-8451 1347-6947 |
| language | eng |
| recordid | cdi_pascalfrancis_primary_926972 |
| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; 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; Free Full-Text Journals in Chemistry |
| subjects | ABA abscisic acid Abscisic Acid - analogs & derivatives Abscisic Acid - biosynthesis Abscisic Acid - chemistry Abscisic Acid - metabolism Analytical, structural and metabolic biochemistry BIOCHEMICAL PATHWAYS Biological and medical sciences BIOSYNTHESIS CERCOSPORA Cercospora cruenta Cercospora rosicola Fundamental and applied biological sciences. Psychology Fungal plant pathogens Glutamic Acid - metabolism Growth regulators Metabolism Mitosporic Fungi - metabolism Other biological molecules Phosphates - metabolism Phytopathology. Animal pests. Plant and forest protection Plant physiology and development Stereoisomerism Substrate Specificity Systematics. Morphology. Development cycle. Physiology Terpenes, steroids. Hormones Thiamine - metabolism α-ionylideneacetic acid γ-ionylideneacetic acid |
| title | Metabolism of chiral ionylideneacetic acids on the abscisic acid biosynthetic pathway in Cercospora |
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