1,2-Hydride Shift in the Biosynthesis of Pinguisane-type Sesquiterpenes

Hiroyuki TAZAKI; Takeshi IWASAKI; Yukihiro KAWAKAMI; Kensuke NABETA

doi:10.1271/bbb.63.1667

Bioscience, Biotechnology, and Biochemistry

Online ISSN : 1347-6947
Print ISSN : 0916-8451

Organic Chemistry Notes

1,2-Hydride Shift in the Biosynthesis of Pinguisane-type Sesquiterpenes

Hiroyuki TAZAKI, Takeshi IWASAKI, Yukihiro KAWAKAMI, Kensuke NABETA

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Keywords: Aneura pinguis, Hepaticae, pinguisone, sesquiterpene, biosynthesis

JOURNAL FREE ACCESS

1999 Volume 63 Issue 9 Pages 1667-1668

DOI https://doi.org/10.1271/bbb.63.1667

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Abstract

A ²H-NMR analysis of 6α-hydroxy-3-oxo-pinguis-5(10)-ene-11,6-olide produced by axenic culture of liverwort Aneura pinguis in the presence of [4-²H₂]-labeled mevalonate clarified the presence of a 1,2-hydride shift and retention of deuterium at the C-4 position in the biosynthesis of pinguisane-type sesquiterpenes from FPP.

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