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Simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (R)-3-fluorolactic acid
Affiliation:1. PETNET Solutions, Heathfield Way, Nottingham City Hospital, Gate 1 Hucknall Road, Nottingham, NG5 1PB, UK;2. Nottingham University Hospitals NHS Trust, PET/CT Centre, Nottingham City Hospital, Gate 1 Hucknall Road, Nottingham, NG5 1PB, UK;3. University of Nottingham, School of Medicine, Queen''s Medical Centre, Derby Road, Nottingham, NG7 2UH, UK;1. Department of Radiology, Washington University School of Medicine, St. Louis, MO 63110, USA;2. Department of Neurology, Washington University School of Medicine, St. Louis, MO 63110, USA;3. Department of Physical Therapy and Occupational Therapy, Washington University School of Medicine, St. Louis, MO 63110, USA
Abstract:A coupled enzymatic system for the simultaneous synthesis of (S)-3-fluoroalanine (1a) and (R)-3-fluorolactic acid (3) with l-alanine dehydrogenase (l-AlaDH) from Bacillus subtilis and rabbit muscle l-lactate dehydrogenase (l-LDH) using rac-1 and NAD+ is described. Analysis of isolated products of the laboratory preparative scale process revealed 1a in 60% yield and 88% ee and 3 in 80% yield and over 99% ee. The compounds 1a and 3 represent chiral building blocks for the synthesis of several products with pharmacological activity.
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