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.

Burkholderia cepacia lipase: A versatile catalyst in synthesis reactions

“…6‐Azauridine (AzUrd) is another nucleoside analog used for therapeutic purposes (Zeng, Lin, & Sartorelli, ) and it was regioselectively acylated using Lipase PS‐D to obtain 3′‐O‐acyl‐azauridine (Wang, Bi, & Zong, , 2012b). This process was considerably easier compared to the traditional chemical pathway that requires multiple steps of protection and deprotection (Pejanović et al, ).…”

Effect of Binary Organic Solvent Mixtures on Lipase-Catalyzed Regioselective Acylation of 6-Azauridine with Various Structural Vinyl Esters

“…In recent years, enzymatic acylation of nucleosides associated with high regioselectivity, mild reaction conditions and environmental friendliness in nonaqueous media has proved to be a practicable option for this purpose. For example, various kinds of 5'-or 3'-O-acyl-nucleosides derivatives were successfully enzymatic synthesized by our group [9][10][11] . Furthermore, among the biocatalysts used extensively, C. antarctica lipase B have undoubtedly proved to be effective catalysts for a great variety of chemical processes, especially towards acylating the 5'-OH of the sugar moiety of many nucleosides 9 .…”