Fig. 4: Stereoselectivity and substrate scope of nicotine biosynthetic cascade.
From: Nicotine biosynthesis is completed by cryptic activating glucosylation
A Stereoselective formation of (S)-nicotine (1). Nicotine formation was achieved through one-pot enzymatic cascade (2, 3, NaGT, NaGR, NicGH) with and without NicGS detected by chiral HPLC (260 nm). Signal intensity of peaks and standards (blue) was scaled for comparison. B Induction of stereoselectivity by NicGS. EIC (m/z 325.2 ± 0.15) showing (R, S)-nicotine glucoside (13) formation from 2 with NaGT, NaGR and NMP, with or without NicGS. Chemically verified standards are blue. Signal intensity was scaled for comparison. C Formation of nornicotine (16) and D anabasine (6) via the nicotine biosynthetic cascade (2, NaGT, NaGR, NicGS, NicGH) with 15 or 8, respectively, either synthesized or formed enzymatically by OLADO.
