The stereochemical course of 2-methylisoborneol biosynthesis.
Binbin GuAnwei HouJeroen S DickschatPublished in: Beilstein journal of organic chemistry (2022)
Both enantiomers of 2-methyllinalyl diphosphate (2-Me-LPP) were synthesized enantioselectively using Sharpless epoxidation as a key step and purification of enantiomerically enriched intermediates through HPLC separation on a chiral stationary phase. Their enzymatic conversion with 2-methylisoborneol synthase (2MIBS) demonstrates that ( R )-2-Me-LPP is the on-pathway intermediate, while a minor formation of 2-methylisoborneol from ( S )-2-Me-LPP may be explained by isomerization to 2-Me-GPP and then to ( R )-2-Me-LPP.