Regioselectivity-reversal in acylation of 6-azauridine catalyzed by Burkholderia cepacia lipase |
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| Authors: | Zhao-Yu Wang Yan-Hong Bi Min-Hua Zong |
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| Institution: | (1) School of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huai’an, 223003, People’s Republic of China;(2) Lab of Applied Biocatalysis, South China University of Technology, Guangzhou, 510640, People’s Republic of China; |
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| Abstract: | 3′-O-Stearoylation of 6-azauridine was achieved enzymatically for the first time. Among eight commercially available lipases,
that from Burkholderia cepacia displayed a 3′-regioselectivity of 80% towards the acylation of 3-hydroxyl of 6-azauridine. Using an immobilized lipase from
Burkholderia cepacia, the 3′-regioselectivities of the acylations could be reversed by lengthening the aliphatic chain of the acyl donors (C2–C18).
The possible reason might be the presence of the interaction between the base moiety and the acyl group. |
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