Absolute structure of N-p-coumaroyloctopamine in elicitor-treated potato tuber tissue |
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Authors: | Matsuda F Miyagawa H Ueno T |
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Affiliation: | Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan. matsuda@colorado.kais.kyoto-u.ac.jp |
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Abstract: | Treatment of potato tuber tissue with beta-1,3-oligoglucosaccharide causes an accumulation of N-p-coumaroyloctopamine (1). In order to determine the absolute structure of 1 in potato, optically active 1 was synthesized from (R)-octopamine which had been obtained from the racemic mixture by the fractional crystallization. By comparing the chromatographic behavior of synthetic and naturally-occurring samples with a chiral HPLC analysis, the absolute configuration of 1 in potato was determined to be S. This indicates that the absolute configuration of the octopamine moiety of 1 is opposite to that of octopamine formed in animal tissues. |
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