Taken together, these results unanimously indicate that the deuterium atoms were retained in the product, with one deuterium atom migrating from C-1 to C-14 through two 1,2-hydride shifts instead of one 1,3-hydride shift (Fig. ). In addition, we chemoenzymatically synthesized 10F-GGPP (see Supplementary Information for detailed synthesis), hypothesizing that the strong electron-withdrawing effect of the fluorine atom might prevent 1,14 cyclization, which might result in the formation of a shunt cembrane product. However, our attempt to incubate it with MicA did not yield the anticipated compounds.