Please use this identifier to cite or link to this item:
http://hdl.handle.net/11375/8944
Title: | Biosynthesis of the Pyrrolidine Ring in Plants |
Authors: | Mestichelli, Louis J.J. |
Advisor: | Spenser, Ian D. |
Department: | Chemistry |
Keywords: | Chemistry;Chemistry |
Publication Date: | Dec-1976 |
Abstract: | <p>DL-[5-³H,5-¹⁴C]ornithine and DL-[2-³H,5-¹⁴C]ornithine were administered to intact tobacco plants (Nicotiana tabacum) in separate experiments. Proline, ornithine and nicotine were isolated. The ³H:¹⁴C ratio in proline derived from DL-[5-³H,5-¹⁴C]ornithine was the same as that in the reisolated ornithine, whereas proline derived from DL-[2-³H,5-¹⁴C]ornithine contained ¹⁴C but lost almost all tritium relative to ¹⁴C. This evidence definitely excludes 5-oxo-2-aminopentanoic acid and Δ¹-pyrroline-5-carboxylic acid as intermediates on the route from ornithine to proline. These results together with earlier work are interpreted to show that proline is derived from ornithine via 2-oxo-5-aminopentanoic acid and Δ¹-pyrroline-2-carboxylic acid. The ³H:¹⁴C ratios found in nicotine samples isolated from experiments using DL-[5-³H,5-¹⁴C]ornithine and DL-[2-³H,5-¹⁴C]ornithine are consistent with the accepted route from ornithine via 1,4-diaminobutane, mono-N-methyl-1,4-diaminobutane, 4-methylaminobutanal, and N-methylpyrrolinium ion. The ³H:¹⁴C ratio found in nicotine derived from DL-[5-³H,5-¹⁴C]ornithine is interpreted as showing that oxidation of mono-N-methyl-1,4-diaminobutane to 4-methylaminobutanal proceeds with loss of the 4(S)-hydrogen.</p> |
URI: | http://hdl.handle.net/11375/8944 |
Identifier: | opendissertations/411 1203 882188 |
Appears in Collections: | Open Access Dissertations and Theses |
Files in This Item:
File | Size | Format | |
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fulltext.pdf | 1.95 MB | Adobe PDF | View/Open |
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