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

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.