108(P-65) 植物培養細胞酵素によるリグナン類の骨格構築反応(ポスター発表の部)

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概要

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• Biocatalysts such as an enzyme, fungus and bacteria have great potential for use in synthetic organic chemistry. In recent years, much attention has been paid to the ability of specific conversion of organic foreign substrates and secondary metabolites to the more useful compounds by cultured plant cells. We had exhibited the ability of enantioselective transformation of organic foreign substrates by using plant cell cultures. Then, we studied the synthesis of lignans as secondary metabolites with plant cell cultures. Construction of the framework of lignans were examined by following methods, 1) ring closure reactions (phenol oxidative coupling) of dibenzylbutanolides; 2) dimerization of trans-ferulic acid, and 3) dediastereomerization of dibenzylbutanolides. Cyclization of 1 to the desired 2 proceeds quantitatively by the cell culture of Camellia sinensis. Dimerization of trans-ferulic acid (3a) failed to afford the vinyl compound 4a through the decarboxylation. A mixture of two diastereomers (4R^*-5) and (4S^*-5) (1: 1 ratio) was subjected to plant cell cultures to give a single diastereomer (4R^*-5) in 80% yield with 100% diastereomeric excess and 0% enantiomeric excess. This novel biocatalytic dediastereomerization method, i. e., reactions allowing the transformation of two diastereomers into one diastereomer in quantitative yield, has been developed for the other substrates with a variety of plant cell cultures.

• 天然有機化合物討論会の論文
• 2001-09-01

著者

• 田中 圭

  静岡県大薬

• 竹元 万寿美

  静岡県大薬

• 加藤 晃一

  静岡県大薬

• 本郷 洋子

  静岡県大薬

• 福与 綾子

  静岡県大薬

• Takemoto Masumi

  School Of Pharmaceutical Sciences(laboratory Of Medicinal Chemistry)

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