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高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (1): 95-98.doi: 10.1007/s40242-012-2249-2

• Articles • 上一篇    下一篇

Preparation of Optically Active Alkoxy-serines from Amino-amide Racemate Catalyzed by Escherichia coli Cells with Peptidase B Activity

WANG Zhi-yuan, LIU Jun-zhong, XU Li-sheng, ZHANG Hong-juan, LIU Qian, JIAO Qing-cai   

  1. State Key Laboratory of Pharmaceutical Biotechnology, School of Life Science, Nanjing University, Nanjing 210093, P. R. China
  • 收稿日期:2012-06-29 修回日期:2012-09-21 出版日期:2013-02-01 发布日期:2013-01-23
  • 基金资助:

    Supported by the National Technology-Innovation Fund of China(No.02CJ-13-01-16) and the Open Fund of State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, China.

Preparation of Optically Active Alkoxy-serines from Amino-amide Racemate Catalyzed by Escherichia coli Cells with Peptidase B Activity

WANG Zhi-yuan, LIU Jun-zhong, XU Li-sheng, ZHANG Hong-juan, LIU Qian, JIAO Qing-cai   

  1. State Key Laboratory of Pharmaceutical Biotechnology, School of Life Science, Nanjing University, Nanjing 210093, P. R. China
  • Received:2012-06-29 Revised:2012-09-21 Online:2013-02-01 Published:2013-01-23
  • Supported by:

    Supported by the National Technology-Innovation Fund of China(No.02CJ-13-01-16) and the Open Fund of State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, China.

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摘要：

Alkoxy-L-serines are useful for peptide syntheses. The demand for alkoxy-L-serines in the pharmaceutical industries continues to increase because of their multiple physiological effects. In this research, an improved method for alkoxy-L-serines synthesis is reported. A series of substrates, DL-β-alkoxy-α-amino propionamides, was used for the synthesis of alkoxy-serines catalyzed by Escherichia coli cells with peptidase B(PepB) activity. The results show that PepB has a high resolution activity with DL-β-alkoxy-α-amino propionamides as substrate. Reaction conditions were optimized, i.e., DL-β-methoxy-α-amino propionamide as substrate at pH=9.0, 40 ℃ and 14 h, and the optimal reaction concentration is 400 mmol/L. The results also show that divalent metal cations exhibit different effects on the PepB activity, for example, Zn2+ and Cu2+ can obviously inhibit the activity of PepB, whereas Co2+, Ca2+, Mn2+ and Mg2+ at low concentrations can activate PepB. This research provides access to enantiomerically enriched and valuable alkoxy-L-serines from a simple amino-amide racemate.

关键词: Alkoxy-serine, DL-β-Alkoxy-α-amino propionamide, Enzymatic resolution, Peptidase B

Abstract:

Alkoxy-L-serines are useful for peptide syntheses. The demand for alkoxy-L-serines in the pharmaceutical industries continues to increase because of their multiple physiological effects. In this research, an improved method for alkoxy-L-serines synthesis is reported. A series of substrates, DL-β-alkoxy-α-amino propionamides, was used for the synthesis of alkoxy-serines catalyzed by Escherichia coli cells with peptidase B(PepB) activity. The results show that PepB has a high resolution activity with DL-β-alkoxy-α-amino propionamides as substrate. Reaction conditions were optimized, i.e., DL-β-methoxy-α-amino propionamide as substrate at pH=9.0, 40 ℃ and 14 h, and the optimal reaction concentration is 400 mmol/L. The results also show that divalent metal cations exhibit different effects on the PepB activity, for example, Zn2+ and Cu2+ can obviously inhibit the activity of PepB, whereas Co2+, Ca2+, Mn2+ and Mg2+ at low concentrations can activate PepB. This research provides access to enantiomerically enriched and valuable alkoxy-L-serines from a simple amino-amide racemate.

Key words: Alkoxy-serine, DL-β-Alkoxy-α-amino propionamide, Enzymatic resolution, Peptidase B