BIOSYNTHESIS OF (+)-CUBENENE AND (+)-EPICUBENOL BY CELL-FREE-EXTRACTS OF CULTURED-CELLS OF HETEROSCYPHUS-PLANUS AND CYCLIZATION OF [H-2]FARNESYL DIPHOSPHATES

被引：23

作者：

NABETA, K ^{[1
]}

KIGURE, K ^{[1
]}

FUJITA, M ^{[1
]}

NAGOYA, T ^{[1
]}

ISHIKAWA, T ^{[1
]}

OKUYAMA, H ^{[1
]}

TAKASAWA, T ^{[1
]}

机构：

[1] OBIHIRO UNIV AGR & VET MED,DIV LIVERAL ART,OBIHIRO,HOKKAIDO 080,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 15期

关键词：

D O I：

10.1039/p19950001935

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute stereochemistry of cubenene and epicubenol from cultured cells of Heteroscyphus planus was determined as both (+)-isomers by H-1 and C-13 NMR spectroscopy, GLC using a chiral capillary column, and optical rotations. Incubation of two geometrical isomers of deuteriated farnesyl diphosphate (FPP) with a cell-free extract from cultured cells indicated that both compounds were specifically formed from (2E,6E)-FPP. Gas-liquid chromatography-mass spectrometry (GLC-MS) and H-2 NMR analyses of(+)-cubenene and (+)-epicubenol generated from [1,1-H-2(2)]- and [6-H-2]-FPP confirmed the presence of 1,2- and 1,3-hydride shifts in their formation.

引用

页码：1935 / 1939

页数：5

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