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. 1970 May;117(5):921-7.
doi: 10.1042/bj1170921.

Aspects of the stereochemistry of torularhodin biosynthesis

R E Tefft, T W Goodwin, K L Simpson

Aspects of the stereochemistry of torularhodin biosynthesis

R E Tefft et al. Biochem J. 1970 May.

Abstract

1. The incorporation of [2-(14)C]acetate, [2-(14)C]mevalonic acid and [2-(14)C,2-(3)H(2)]-mevalonic acid into torulene and torularhodin by Rhodotorula rubra and Rhodotorula glutinis was studied. 2. A recovery of 14.3% of the label was obtained on decarboxylation of the torularhodin biosynthesized from [2-(14)C]mevalonic acid. 3. An analysis of the (3)H/(14)C ratio in torularhodin gave a value of 9.44:8. 4. These results, obtained by different experimental techniques, show that the reactions in the conversion of the dimethyl group of isopentenyl pyrophosphate into the 16',17'-position of torularhodin must be free from randomization. A mechanism for the isomerization of isopentenyl pyrophosphate to dimethylallyl pyrophosphate is suggested.

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