BIOSYNTHESIS OF 1α,2α,3β-TRIHYDROXY-p-METHANE BY FUSICOCCUM AMYGDALI

Article abstract of DOI:10.1016/0031-9422(81)80109-4

Measurement of isotope ratios in 1α,2α3β-trihydroxy-p-methane, which has been biosynthesized in Fusicoccum amygdali from ³H- and ¹⁴C-labelled mevalonate and in its degradation product diosphenol indicates that: (a) four tritium atoms arising from <5-²H2, 2-¹⁴C>MVA are retained, one more than suggested from the hydroxylation pattern, (b) menth-2-ene-1-ol is generated from an α-terpinyl cation through a 1,3-hydride shift and (c) trans-cleavage of an α-epoxide by hydrolysis gives 1α,2α,3β-trihydroxy-p-methane. - Keywords: Fusicoccum amygdali; biosynthesis; monoterpenes; 1α,2α,3β-trihydroxy-p-methane; α-terpinyl cation; diosphenol.