Synthesis of Aromatic 1,2-Amino Alcohols Utilizing a Bienzymatic Dynamic Kinetic Asymmetric Transformation

✍ Scribed by Johannes Steinreiber; Martin Schürmann; Friso van Assema; Michael Wolberg; Kateryna Fesko; Christoph Reisinger; Daniel Mink; Herfried Griengl

• Book ID: 101423607
• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 443 KB
• Volume: 349
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200700051

✦ Synopsis

Abstract

The applicability of the recent published bienzymatic protocol for the synthesis of (R)‐2‐amino‐1‐phenylethanol was tested using L‐threonine aldolase from Pseudomonas putida and l‐tyrosine decarboxylase from either Enterococcus faecalis (Efa) or two genes from Enterococcus faecium (Efi1, Efi2). In all 21 benzaldehyde derivatives were applied for an initial TLC screening. On a small scale, octopamine and noradrenaline were obtained as (S)‐enantiomers using Efi1. Three protocols were up‐scaled yielding enantioenriched (S)‐octopamine (yield 99 %, ee 81 %), (R)‐2‐amino‐1‐phenylethanol (yield 61 %, ee 62 %) and (S)‐noradrenaline (yield 76 %, ee 79 %).