| Biosynthesis of slaframine, (1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizine, a parasympathomimetic alkaloid of fungal origin. 4. Metabolic fate of ethyl pipecolylacetate, 1,3-dioxooctahydroindolizine, and 1-hydroxyoctahydroindolizine in Rhizoctonia leguminicola. | |
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MedLine Citation:
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PMID: 476078 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Known or suspected intermediates in the biosynthesis of slaframine and 3,4,5-trihydroxyoctahydro-1-pyrindine, piperidine alkaloids of the phytopathogenic fungus Rhizoctonia leguminicola, were prepared and tested for biological conversions. Ethyl pipecolylacetate, an analogue of the postulated condensation product of pipecolic and malonic acids (two previously identified alkaloid precursors), was insufficiently stable for feeding experiments. The lactam of pipecolylacetate, 1,3-dioxooctahydroindolizine, was degraded by the fungus without direct incorporation into alkaloids. The known slaframine precursor 1-hydroxyoctahydroindolizine was prepared by a novel route which permitted high levels of deuterium enrichment at C-1 and C-3. Mass spectrometric examination of the slaframine biosynthesized from cis- and trans-[1,3,3-2H]-1-hydroxyoctahydroindolizine strengthened arguments that 1-oxooctahydroindolizine is an intermediate in slaframine biogenesis. |
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Authors:
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E C Clevenstine; P Walter; T M Harris; H P Broquist |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Biochemistry Volume: 18 ISSN: 0006-2960 ISO Abbreviation: Biochemistry Publication Date: 1979 Aug |
Date Detail:
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Created Date: 1979-11-21 Completed Date: 1979-11-21 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0370623 Medline TA: Biochemistry Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 3663-7 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Carbon Radioisotopes Deuterium Indolizines / metabolism* Isotope Labeling Magnetic Resonance Spectroscopy Mass Spectrometry Mitosporic Fungi / metabolism* Pipecolic Acids / metabolism* Rhizoctonia / metabolism* Tritium |
| Chemical | |
Reg. No./Substance:
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0/Carbon Radioisotopes; 0/Indolizines; 0/Pipecolic Acids; 10028-17-8/Tritium; 7782-39-0/Deuterium |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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