Studies on a mevaldic acid reductase of rat liver

Isoprenoids in three-dimensional space: the stereochemistry of terpene biosynthesis

“…Conclusively, the generated compound was (1S)-[1-3 H]farnesol, and because this stereochemistry must be conserved from 4, the reduction of 10 proceeds by 5Si attack. 26 A similar experiment was performed using pig liver and rat liver ''mevaldate reductase'' that show opposed hydride addition to the 5Re face of 10, 27 but this enzyme unspecifically reduces both (R)-and (S)-mevaldate 28 and was later reclassified as an aldehyde reductase that is not involved in the mevalonate pathway. 29 In contrast to the ''mevaldate reductase'', the HMG-CoA reductase is highly stereospecific with respect to the substrate's 3-positions and accepts only (3S)-3 or (3S)-9, whereas the enzyme is flexible for the stereochemistry of the thiohemiacetal and reacts on both diastereomers of (3S,5RS)-9.…”