Unexpected reversal of the regioselectivity in Thermomyces lanuginosus lipase-catalyzed acylation of floxuridine |
| |
Authors: | Ning Li Min-Hua Zong Ding Ma |
| |
Affiliation: | (1) Lab of Applied Biocatalysis, College of Light Industry and Food Sciences, South China University of Technology, 510640 Guangzhou, China;(2) State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023 Dalian, China |
| |
Abstract: | Unexpected inversion of the 3′:5′-regioselectivity was observed in the enzymatic methacryloylation, crotonylation and cinnamoylation of floxuridine (1.5:1, 2.3:1 and 4.4:1, respectively), where Thermomyces lanuginosus lipase preferentially catalyzed the acylation of 3′-hydroxyl rather than that of 5′-hydroxyl group. The possible reason might be the presence of a remote interaction between the unsaturated bond in the acyl group and the aromatic ring of amino acid residue Trp89 in the lid of the lipase. Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users. |
| |
Keywords: | Enzymatic acylation Floxuridine Nucleoside Reversal of regioselectivity Thermomyces lanuginosus lipase |
本文献已被 SpringerLink 等数据库收录! |
|