Asymmetric biosynthesis of (1S, 2S)-ephedrine by Morganella morganii CMCC(B)49208

Abstract

(1S, 2S)-Ephedrine, one of the four ephedrine isomers, is a common pharmacological agent; however, it is difficult to synthesize in a stereospecific manner using traditional organic synthesis. In this paper, a novel enzymatic process was developed for the stereoselective synthesis of (1S, 2S)-ephedrine. Morganella morganii CMCC(B)49208 was found to asymmetrically reduce the prochiral carbonyl compound 1-phenyl-1-oxo-2-methylaminopropane (MAK) to optically pure (1S, 2S)-ephedrine which was measured with thin layer chromatography (TLC) and high performance liquid chromatography (HPLC) technologies. In addition, a conversion process using air-dried M. morganii CMCC(B)49208 cells was developed to produce (1S, 2S)-ephedrine at a final concentration of 0.852 gL-1 (>99% ee) and 84.4% molar yield.