title: Absolute structure of N-p-coumaroyloctopamine in elicitor-treated potato tuber tissue.
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.
authors.affiliation: Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan. matsuda@colorado.kais.kyoto-u.ac.jp
authors.forename: F
authors.initials: F
authors.lastname: Matsuda
authors.forename: H
authors.initials: H
authors.lastname: Miyagawa
authors.forename: T
authors.initials: T
authors.lastname: Ueno
mesh_terms: D003373:Coumaric Acids / Q000737:chemistry*; D015394:Molecular Structure; D009655:Octopamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D009844:Oligosaccharides; D011198:Solanum tuberosum / Q000737:chemistry*
chemical_list: D003373:Coumaric Acids; C410948:N-4-coumaroyloctopamine; D009844:Oligosaccharides; D009655:Octopamine