Abstract
A new practical approach to the preparation of highly and multiply deuterated isoprenoids, archaeal membrane lipid, diterpene antibiotic terpentecin, and carotenoids as examples, and its potential for analyzing the biosynthetic mechanism of isoprenoids are described by using fully deuterated mevalonolactone (MVL-d9). Racemic MVL-d9 was successfully synthesized starting from deuterated dimethoxyphenyl-acetone and trimethyl phosphonoacetate in gram scale. Enantiomerically pure (R) -MVL-d9 was also synthesized using Sharpless asymmetric epoxidation. The methodology for biosynthetic studies using MVL-d9 is meritorious for mechanistic enzymology, particularly, the key transformation involving proton attack and/or proton quench as observed in isoprenoids biosynthesis.
