Biosynthesis of (–)-β-barbatene from 13C- and 2H-labelled acetate, mevalonate and glycerol†

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Kensuke Nabeta, Kaori Komuro, Tomoaki Utoh, Hiroyuki Tazaki, Kensuke Nabeta and Hiroyuki Koshino


Abstract

The 2H and 13C enrichment, 13C–13C coupling patterns and β-2H isotope shifts observed in β-barbatanol prepared from (–)-β-barbatene incorporating variously 2H- and 13C-labelled mevalonates, acetates and glycerol verifies a 1,4-hydrogen shift and a double 1,2-methyl migration in the formation of β-barbatene in cultured cells of Heteroscyphus planus, and also indicates the diversity of regulation and the sole operation of the mevalonate pathway in extrachloroplastidic sesquiterpene biosynthesis.


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