earticle

영어

Fluorinated alpha-hydroxyacids and alpha-amino acids are considered to be highly versatile chiral building blocks in asymmetric synthesis for the production of several compounds of pharmacological interest. 3-fluoro-L-alanine is recognized as an antibiotic via irreversible
inactivation of bacterial alanine racemase. It also acts as an inhibitor of serine palmitoyl transferase and it is a potential precursor for the synthesis of fuoroamino compounds. Asymmetric synthesis of an unnatural amino acid was demonstrated by omega-transaminase from Vibrio fluvialis JS17. 3-fluoro-L-alanine was synthesized from 3- fluoropyruvate and (S)-alphabenzylamine with an enantiomeric excess higher than 99%. The reaction showed severe product inhibition by acetophenone, which was overcome by employing a biphasic reaction
system to remove the inhibitory product from the aqueous phase. When a biphasic reaction was carried out with 100 mM 3-fluoropyruvate and 125 mM (S)-alphabenzylamine using isooctane as
an extractant, conversion of 3-fluoropyruvate reached 98%.