Chinese Journal of Catalysis

Chinese Journal of Catalysis ›› 2011, Vol. 32 ›› Issue (2): 357-361.DOI: 10.3724/SP.J.1088.2011.00901

• Research papers • Previous Articles     Next Articles

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

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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