Dezembro 2013 vol. 1 num. 2 - Brazilian Meeting on Organic Synthesis 2013

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Efficient Asymmetric Synthesis of Lamivudine and its enantiomer via Enzymatic Dynamic Kinetic Resolution

Hu, Lei ; Schaufelberger, Fredrik ; Zhang, Yan ; Ramström, Olof ;

Abstract:

In the last decade, lamivudine has been one of the most successful drugs for the treatment of HIV as well as chronic Hepatitis B. It inhibits both type 1 and 2 of the human HIV reverse transcriptase and also the reverse transcriptase of hepatitis B in vitro. Although there are many reported syntheses for the isomerically pure lamivudine, most of them introduce the chiral 1,3-oxathiolane motif by either crystallization of the correct isomer from a racemic mixture, or by enzymatic hydrolysis/acetylation of the other stereoisomers. The main drawback of those methods is the great loss in yield, as no more than 50% yield could be obtained while maintaining high stereoselectivity, due to the nature of the kinetic resolution.

Abstract:

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Palavras-chave: Dynamic kinetic resolution, Enzyme, Nucleoside, Asymmetric synthesis,

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013101412329

Referências bibliográficas
  • [1] 1 Romeo, G.; Chiacchio, U.; Corsaro, A.; Merino, P. Chem. Rev.2010, 110, 3337.
Como citar:

Hu, Lei; Schaufelberger, Fredrik; Zhang, Yan; Ramström, Olof; "Efficient Asymmetric Synthesis of Lamivudine and its enantiomer via Enzymatic Dynamic Kinetic Resolution", p. 128 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-15bmos-BMOS2013_2013101412329

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