THE BIOSYNTHESIS OF TROPIC ACID IN PLANTS - EVIDENCE FOR THE DIRECT REARRANGEMENT OF 3-PHENYLLACTATE TO TROPATE
Dual labelled sodium (RS)-3-phenyl[2-C-13,2-H-2]lactate was incubated with transformed root cultures of Datura stramonium and the incorporation of the label into the tropic acid ester moiety of hyoscyamine was assessed by C-13{H-1} and C-13{H-1,H-2} NMR spectroscopy and by GC-MS analysis. It is demo...
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Published in | Journal of the Chemical Society, Perkin Transactions 1 no. 9; pp. 1159 - 1162 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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CAMBRIDGE
Royal Soc Chemistry
1994
Royal Society of Chemistry |
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Abstract | Dual labelled sodium (RS)-3-phenyl[2-C-13,2-H-2]lactate was incubated with transformed root cultures of Datura stramonium and the incorporation of the label into the tropic acid ester moiety of hyoscyamine was assessed by C-13{H-1} and C-13{H-1,H-2} NMR spectroscopy and by GC-MS analysis. It is demonstrated that the C-13-H-2 bond of sodium (RS)-3-phenyl[2-C-13,2-H-2]lactate is incorporated (GC-MS, M + 2, 17%) intact into the hydroxymethyl group at C-3' of the (S)-tropoyl moiety. This result demonstrates unambiguously that 3-phenyllactate is a closer precursor to the tropate ester than phenylpyruvate or phenylalanine. |
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AbstractList | Dual labelled sodium (RS)-3-phenyl[2-C-13,2-H-2]lactate was incubated with transformed root cultures of Datura stramonium and the incorporation of the label into the tropic acid ester moiety of hyoscyamine was assessed by C-13{H-1} and C-13{H-1,H-2} NMR spectroscopy and by GC-MS analysis. It is demonstrated that the C-13-H-2 bond of sodium (RS)-3-phenyl[2-C-13,2-H-2]lactate is incorporated (GC-MS, M + 2, 17%) intact into the hydroxymethyl group at C-3' of the (S)-tropoyl moiety. This result demonstrates unambiguously that 3-phenyllactate is a closer precursor to the tropate ester than phenylpyruvate or phenylalanine. |
Author | OHAGAN, D ROBINS, RJ CHESTERS, NCJE |
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Keywords | TRANSFORMED ROOT CULTURES 1,2-MIGRATION CHEMISTRY PHENYLALANINE PRECURSORS DATURA-STRAMONIUM L ALKALOIDS Datura stramonium Biosynthesis NMR spectrometry Mechanism Gas chromatography Alkaloid Carboxylic acid Dicotyledones Angiospermae Spermatophyta Biosynthesis precursor Solanaceae Mass spectrometry |
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References | ROBINS, RJ (WOS:A1994NC13800003) 1994 LEETE, E (WOS:A1983QN35400023) 1983; 22 LEETE, E (WOS:A1975AW22500038) 1975; 97 ANSARIN, M (WOS:A1993LW18200002) 1993; 56 ROBINS RJ (WOS:A1994NL11400008.16) GARSON MJ (WOS:A1994NL11400008.7) 1979 ROBINS, RJ (WOS:A1991ET35700007) 1991; 183 LEETE, E (WOS:A1979HA53600001) 1979; 36 EVANS, WC (WOS:A1976BJ96600010) 1976; 15 LEETE, E (WOS:A1974T815200035) 1974; 13 LEETE, E (WOS:A1987F918100036) 1987; 65 LEETE, E (WOS:A1990DU71300001) 1990; 56 KITAMURA, Y (WOS:A1992JB78900004) 1992; 140 DRAGER, B (WOS:A1992JZ02900018) 1992; 188 COX, RJ (WOS:A1991GK05700036) 1991 LEETE, E (WOS:A1984TS61700083) 1984; 106 ANSARIN, M (WOS:A1993KU24900019) 1993; 32 ANSARIN M (WOS:A1994NL11400008.1) |
References_xml | – volume: 32 start-page: 1183 year: 1993 ident: WOS:A1993KU24900019 article-title: THE BIOSYNTHESIS OF TROPIC ACID .4. THE OBLIGATORY ROLE OF PHENYLLACTATE IN THE BIOSYNTHESIS OF TROPIC ACID publication-title: PHYTOCHEMISTRY contributor: fullname: ANSARIN, M – volume: 65 start-page: 226 year: 1987 ident: WOS:A1987F918100036 article-title: CHEMISTRY OF THE TROPANE ALKALOIDS .35. STEREOCHEMISTRY OF THE 1,2-MIGRATION OF THE CARBOXYL GROUP THAT OCCURS DURING THE BIOSYNTHESIS OF TROPIC ACID FROM PHENYLALANINE publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE contributor: fullname: LEETE, E – volume: 56 start-page: 339 year: 1990 ident: WOS:A1990DU71300001 article-title: RECENT DEVELOPMENTS IN THE BIOSYNTHESIS OF THE TROPANE ALKALOIDS publication-title: PLANTA MEDICA contributor: fullname: LEETE, E – ident: WOS:A1994NL11400008.16 publication-title: IN PRESS PLANTA contributor: fullname: ROBINS RJ – volume: 56 start-page: 1211 year: 1993 ident: WOS:A1993LW18200002 article-title: THE BIOSYNTHESIS OF TROPIC ACID .3. COMPETITIVE FEEDING EXPERIMENTS WITH TROPIC ACID PRECURSORS IN DATURA publication-title: JOURNAL OF NATURAL PRODUCTS contributor: fullname: ANSARIN, M – volume: 22 start-page: 933 year: 1983 ident: WOS:A1983QN35400023 article-title: CHEMISTRY OF THE TROPANE ALKALOIDS .32. FAILURE OF 3-HYDROXY-3-PHENYLPROPANOIC ACID AND CINNAMIC ACID TO SERVE AS PRECURSORS OF TROPIC ACID IN DATURA-INNOXIA publication-title: PHYTOCHEMISTRY contributor: fullname: LEETE, E – start-page: 615 year: 1994 ident: WOS:A1994NC13800003 article-title: BIOSYNTHESIS OF HYOSCYAMINE INVOLVES AN INTRAMOLECULAR REARRANGEMENT OF LITTORINE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: ROBINS, RJ – volume: 15 start-page: 287 year: 1976 ident: WOS:A1976BJ96600010 article-title: BIOSYNTHESIS OF C-6-C-3 ACIDS IN DATURA-INNOXIA publication-title: PHYTOCHEMISTRY contributor: fullname: EVANS, WC – volume: 140 start-page: 141 year: 1992 ident: WOS:A1992JB78900004 article-title: CONVERSION OF PHENYLALANINE AND TROPIC ACID INTO TROPANE ALKALOIDS BY DUBOISIA-LEICHHARDTII ROOT CULTURES publication-title: JOURNAL OF PLANT PHYSIOLOGY contributor: fullname: KITAMURA, Y – start-page: 2537 year: 1991 ident: WOS:A1991GK05700036 article-title: SYNTHESIS OF ISOTOPICALLY LABELED 3-AMINO-2-PHENYLPROPIONIC ACID AND ITS ROLE AS A PRECURSOR IN THE BIOSYNTHESIS OF TENELLIN AND TROPIC ACID publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: COX, RJ – start-page: 539 year: 1979 ident: WOS:A1994NL11400008.7 publication-title: CHEM SOC REV contributor: fullname: GARSON MJ – volume: 188 start-page: 581 year: 1992 ident: WOS:A1992JZ02900018 article-title: LEVELS OF TROPINONE-REDUCTASE ACTIVITIES INFLUENCE THE SPECTRUM OF TROPANE ESTERS FOUND IN TRANSFORMED ROOT CULTURES OF DATURA-STRAMONIUM L publication-title: PLANTA contributor: fullname: DRAGER, B – volume: 13 start-page: 1501 year: 1974 ident: WOS:A1974T815200035 article-title: BIOSYNTHESIS OF TROPIC ACID - FEEDING EXPERIMENTS WITH CINNAMOYLTROPINE AND LITTORINE publication-title: PHYTOCHEMISTRY contributor: fullname: LEETE, E – volume: 97 start-page: 6826 year: 1975 ident: WOS:A1975AW22500038 article-title: USE OF C-13 NUCLEAR MAGNETIC-RESONANCE TO ESTABLISH THAT BIOSYNTHESIS OF TROPIC ACID INVOLVES AN INTRAMOLECULAR REARRANGEMENT OF PHENYLALANINE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: LEETE, E – ident: WOS:A1994NL11400008.1 publication-title: IN PRESS PHYTOCHEMIS contributor: fullname: ANSARIN M – volume: 36 start-page: 97 year: 1979 ident: WOS:A1979HA53600001 article-title: BIOSYNTHESIS AND METABOLISM OF THE TROPANE ALKALOIDS publication-title: PLANTA MEDICA contributor: fullname: LEETE, E – volume: 183 start-page: 185 year: 1991 ident: WOS:A1991ET35700007 article-title: STUDIES ON THE BIOSYNTHESIS OF TROPANE ALKALOIDS IN DATURA-STRAMONIUM L TRANSFORMED ROOT CULTURES .1. THE KINETICS OF ALKALOID PRODUCTION AND THE INFLUENCE OF FEEDING INTERMEDIATE METABOLITES publication-title: PLANTA contributor: fullname: ROBINS, RJ – volume: 106 start-page: 7271 year: 1984 ident: WOS:A1984TS61700083 article-title: CHEMISTRY OF THE TROPANE ALKALOIDS .34. 1,2-MIGRATION OF HYDROGEN DURING THE BIOSYNTHESIS OF TROPIC ACID FROM PHENYLALANINE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: LEETE, E |
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Snippet | Dual labelled sodium (RS)-3-phenyl[2-C-13,2-H-2]lactate was incubated with transformed root cultures of Datura stramonium and the incorporation of the label... |
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SubjectTerms | Alcaloids Analytical, structural and metabolic biochemistry Biological and medical sciences Chemistry Chemistry, Organic Fundamental and applied biological sciences. Psychology Heterocyclic compounds, pigments Other biological molecules Physical Sciences Science & Technology |
Title | THE BIOSYNTHESIS OF TROPIC ACID IN PLANTS - EVIDENCE FOR THE DIRECT REARRANGEMENT OF 3-PHENYLLACTATE TO TROPATE |
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