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Asymmetric biosynthesis of
(1S, 2S)-ephedrine by Morganella morganii
CMCC(B)49208
Liang Zhang1, 2, Zhong-Yang Ding 2
and Gui-Yang Shi1, 2*
1The
Key Laboratory of Industrial Biotechnology, Ministry of
Education, Jiangnan University, Wuxi 214122, China.
2Center
for Bioresource and Bioenergy, School of Biotechnology,
Jiangnan University, Wuxi 214122, China.
*Corresponding author. E-mail:
biomass_jnu@126.com.
Tel./Fax: +86-510-85918229.
Accepted
23 January, 2009 |
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(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.
Key
words:
Ephedrine, stereoselective reduction, Morganella morganii,
bioconversion. |
