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© 2021 The Authors. ChemBioChem published by Wiley–VCH GmbHWe present a one–pot cascade for the synthesis of phenylpropanolamines (PPAs) in high optical purities (er and dr up to >99.5 %) and analytical yields (up to 95 %) by using 1–phenylpropane–1,2–diols as key intermediates. This bioamination entails the combination of an alcohol dehydrogenase (ADH), an ω–transaminase (ωTA) and an alanine dehydrogenase to create a redox–neutral network, which harnesses the exquisite and complementary regio– and stereo–selectivities of the selected ADHs and ωTAs. The requisite 1–phenylpropane–1,2–diol intermediates were obtained from trans– or cis–β–methylstyrene by combining a styrene monooxygenase with epoxide hydrolases. Furthermore, in selected cases, the envisioned cascade enabled to obtain the structural isomer (1S,2R)–1–amino–1–phenylpropan–2–ol in high optical purity (er and dr >99.5 %). This is the first report on an enzymatic method that enables to obtain all of the four possible PPA stereoisomers in great enantio– and diastereo–selectivity.
