Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (07): 1032-1042. Previous Articles     Next Articles

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PS IM催化核苷类化合物3-酯选择性合成中的底物识别

王朝宇*,1,2,宗敏华2   

  1. (1淮阴工学院生命科学与化学工程学院 淮安 223003)
    (2华南理工大学应用生物催化研究室 广州 510640)
  • 收稿日期:2010-09-02 修回日期:2011-02-11 发布日期:2011-02-23
  • 通讯作者: 王朝宇 E-mail:biowzy@126.com

Substrate Recognition of the PS IM in Regioselective Synthesis of Nucleoside Analogs 3-O-Esters

Wang Zhaoyu*,1,2Zong Minhua2   

  1. (1 School of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003)
    (2 Laboratory of Applied Biocatalysis, South China University of Technology, Guangzhou 510640)
  • Received:2010-09-02 Revised:2011-02-11 Published:2011-02-23
  • Contact: Zhao-Yu WANG E-mail:biowzy@126.com

Regioselective enzymatic acylations of nucleosides with vinyl esters in organic solvents were studied for the preparation of 3-O-esters of the nucleosides. The influence of R1 substituent in the nucleosides on 3-OH regioselective acylation catalyzed by Burkholderia cepacia liapse was investigated. The results revealed that the immobilized lipase of PS IM from Burkholderia cepacia showed the highest regioselectivity towards the 3-OH of nucleosides (90%~>99%) among the lipases tested. Moreover, the 3-regioselectivity enhanced not only with the increment of the aliphatic chain of the acyl donors (C6, C10 and C14), but also with the increasing hydrophobicity of R1 group of 2-deoxynucleosides. These observations were mainly attributed to the specific structure feature of the PS IM.

Key words: PS IM, nucleoside analogs, regioselective acylation, substrate recognition

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