Production of(S)-nicotine by enzymatic-chemical cascade catalysis
The traditional synthesis method of(S)-nicotine involves complex steps and relies on multiple chemical catalysts.Herein,a enzymatic-chemical cascade pathway was designed to achieve the green synthesis of(S)-nicotine.Firstly,a coupling system of imine reductase(IRED)and formate dehydrogenase(FDH)was constructed to catalyzed the synthesis of(S)-nornicotine from myosmine as substrate,then(S)-nicotine was prepared via Eschweiler-Clarke reaction of(S)-nornicotine.The IRED and FDH enzyme-containing cells and enzyme solution were obtained from E.coli expression system and the effects of pH and temperature on the enzyme activity of IRED and FDH were investigated.The yield of(S)-nornicotine reached>98%with enantiomeric excess(e.e.)value of>99%under the optimal reaction conditions of temperature 30℃,pH 7.5,myosmine mass concentration 30 g/L,FDH cells 600 U/L,IRED cells 900 U/L,NADP+ 0.6 mmol/L and sodium formate mass concentration 90 g/L.Finally,(S)-nicotine with a yield and e.e.value of above 99%was obtained by chemical methylation of(S)-nornicotine.
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