Absolute Structure ofN-p-Coumaroyloctopamine in Elicitor-treated Potato Tuber Tissue | Zendy

Fumio Matsuda | Zendy; Hisashi Miyagawa | Zendy; Tamio Ueno | Zendy

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Absolute Structure ofN-p-Coumaroyloctopamine in Elicitor-treated Potato Tuber Tissue

Author(s) -

Fumio Matsuda,

Hisashi Miyagawa,

Tamio Ueno

Publication year - 2000

Publication title -

bioscience biotechnology and biochemistry

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.64.625

Subject(s) - absolute configuration , moiety , octopamine (neurotransmitter) , elicitor , chemistry , crystallization , high performance liquid chromatography , stereochemistry , chromatography , organic chemistry , biochemistry , receptor , serotonin , enzyme

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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