催化学报

催化学报 ›› 2011, Vol. 32 ›› Issue (2): 357-361.DOI: 10.3724/SP.J.1088.2011.00901

• 研究论文 • 上一篇    下一篇

核苷中 2'-位取代基对 Burkholderia cepacia 脂肪酶选择性酰化核苷的影响

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, 江苏淮安 223003;  2 华南理工大学应用生物催化研究室, 广东广州 510640
  • 收稿日期:2010-09-03 修回日期:2010-11-19 出版日期:2011-01-26 发布日期:2014-06-25

Influence of 2'-Substituent in the Nucleosides on Burkholderia cepacia Li-pase-Catalyzed Regioselective Acylation

WANG Zhaoyu1, 2,*, ZONG Minhua2   

  1. 1School of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huai’an 223003, Jiangsu, China; 2Laboratory of Applied Biocatalysis, South China University of Technology, Guangzhou 510640, Guangdong, China
  • Received:2010-09-03 Revised:2010-11-19 Online:2011-01-26 Published:2014-06-25

PDF

920

摘要： 研究了核苷结构中 2'-位含有不同取代基时 Burkholderia cepacia 脂肪酶促 3'-位羟基高区域选择性酰化反应. 结果表明, 该脂肪酶催化核苷类似物酰化的优势产物均为 3'-酯, 且随着酰基供体链的增长, 3'-区域选择性逐渐升高; 在酶促核苷癸酰化反应中, 当核苷 2'-位含有 H, F, Cl 和 Br 取代基时, 3'-区域选择性最高 (89%~98%); 当 2'-位含有 OH 或 OCH3 时, 3'-区域选择性较低 (69%~74%).

关键词: 核苷类似物, 选择性酰化, 酶催化, 底物识别

Abstract: The influence of 2'-differing substituent in the nucleosides on 3'-OH regioselective acylation catalyzed by Burkholderia cepacia lipase was investigated. The results revealed that the dominant products in the Burkholderia cepacia lipase-catalyzed acylation proved to be 3'-O-esters and the 3'-regioselectivity increased with the elongation of the aliphatic chain of the acyl donors. Burkholderia cepacia liapse displayed excellent 3'-regioselectivity (89%–98%) in the decanoylation of nucleoside analogs possessing 2'-substitute (such as H, F, Cl, and Br), while low 3'-regioselectivity (69%–74%) to the OH and OCH3 substitute in 2'-position.

Key words: nucleoside analog, regioselective acylation, enzyme catalysis, substrate recognition