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Suprafacial protonation/deprotonation by IDI-2 revealed by chiral methyl analysis. IPP analogues 20 and 21 yield DMAPP products with distinct enantiomeric configurations at the (E)-methyl group, suggesting that protonation at C4 and deprotonation at C2 occur from the face of the isoprene molecule that is exposed to the flavin in the crystal structure.
