Abstract
We achieved the effective controllable regioselective acylation of the primary hydroxyl group of uridine derivatives catalyzed by Lipase TL IM from Thermomyces lanuginosus with excellent conversion and regioselectivity. Various reaction parameters were studied. These regioselective acylations performed in continuous flow microreactors are a proof-of-concept opening the use of enzymatic microreactors in uridine derivative biotransformations.
Highlights
Li-Hua Du, *a Jia-Hong Shen, a Zhen Dong,a Na-Ni Zhou, a Bing-Zhuo Cheng,a Zhi-Min Oua and Xi-Ping Luob
Providing a precise control over different reaction parameters, microreactor technology (MRT) allows for simple screening and optimization of reaction conditions
We found that the reaction of 5- uorouridine (1c) to vinyl laurate (2b) can get a higher yield (99%, entry 10) compared with uridine (98%, entry 6) under the same reaction conditions, it indicated that electron-withdrawing group could improve the acylation reactivity of uridine
Summary
The separation of catalysts and products is very easy when heterogeneous catalysts are packed in continuous- ow columns.[13,14] Nucleoside analogues, such as azidothymidine, telbivudine and doxi uridine, have shown high effectiveness as antiviral[15] and antitumor[16] agents (Fig. 1). Their efficiency is sometimes reduced by the appearance of resistance mechanisms.[17] the search for new nucleoside derivatives has attracted more and more attention from chemists. Scheme 1 Enzymatic synthesis of uridine esters from uridine derivatives and vinyl esters in continuous flow microreactors.
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