New enzymatic two-step cascade reaction for the preparation of a key intermediate for the taxol side-chain

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21 Citations (Scopus)

Abstract

Enzymatic strategies are reported for the synthesis of (2R, 3S)-3-amino-2-hydroxy-3-phenylpropionic acid (ee > 98%), a key intermediate of the side-chain of Taxol®by enzymatic hydrolysis in organic media. The new enzymatic cascade reaction, which took place through Candida antarctica lipase B-catalysed deacylation followed by lactam ring-opening of racemic cis-3-acetoxy-4-phenylazetidin-2-one with H2O in iPr2O at: 60 °C, resulted in two different enantiopure products (ee ≥ 98%), one of them being the desired key intermediate for the side-chain of Taxol®.

Original languageEnglish
Pages (from-to)3074-3079
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number16
DOIs
Publication statusPublished - Jun 1 2010

Keywords

  • Amino acids
  • Anticancer agents
  • Enzyme catalysis
  • Hydrolysis
  • Lactams
  • Taxol

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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