title: Regioselectivity-reversal in acylation of 6-azauridine catalyzed by Burkholderia cepacia lipase.
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.
authors: School of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huai'an, 223003, People's Republic of China.
authors: Zhao-Yu
authors: ZY
authors: Wang
authors: Yan-Hong
authors: YH
authors: Bi
authors: Min-Hua
authors: MH
authors: Zong
mesh_terms: D000215:Acylation; D001380:Azauridine / Q000378:metabolism*; D016956:Burkholderia cepacia / Q000201:enzymology* / Q000378:metabolism*; D004800:Enzymes, Immobilized / Q000378:metabolism; D008049:Lipase / Q000378:metabolism*; D013379:Substrate Specificity
chemical_list: D004800:Enzymes, Immobilized; D001380:Azauridine; D008049:Lipase