Thermomyces lanuginosus lipase-catalyzed regioselective acylation of nucleosides: Enzyme substrate recognition |
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Authors: | Ning Li Min-Hua Zong Ding Ma |
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Institution: | aLaboratory of Applied Biocatalysis, South China University of Technology, Guangzhou 510640, China;bState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China |
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Abstract: | Substrate recognition of Thermomyces lanuginosus lipase in the acylation of nucleosides was revealed through rational substrate engineering for the first time. T. lanuginosus lipase displayed higher catalytic activities and excellent 5′-regioselectivities (94–>99%) in the acylation of ribonucleosides 1f–1j as compared to those in the acylation of 2′-deoxynucleosides 1a–1e. The higher reaction rates and excellent 5′-regioselectivities might derive from a favorable hydrogen bonding between the 2′-hydroxyl group of 1f–1j and phenolic hydroxyl group of Tyr21 present in the hydrophilic region of the lipase. |
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Keywords: | Thermomyces lanuginosus lipase Nucleoside Substrate recognition Substrate engineering Enzymatic acylation Regioselectivity |
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