Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation

Santosh Kumar Padhi, D. Titu, N. Ganesh Pandian, Anju Chadha

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

Deracemisation of aryl substituted β-hydroxy esters by immobilised whole cells of Candida parapsilosis ATCC 7330 gave >99% ee and up to 75% yield of their corresponding (S)-enantiomers. Mechanistic investigation of the deracemisation reaction carried out using a deuterated substrate, ethyl 3-deutero-3-hydroxy-3-phenyl propanoate revealed that while the (S)-enantiomer remains unreacted the (R)-enantiomer undergoes enantioselective oxidation to its corresponding ketoester, which on complementary enantiospecific reduction gives the (S)-enantiomer in high yield and % ee.

Original languageEnglish (US)
Pages (from-to)5133-5140
Number of pages8
JournalTetrahedron
Volume62
Issue number21
DOIs
StatePublished - May 22 2006

Bibliographical note

Funding Information:
We thank CSIR, New Delhi for the financial support.

Keywords

  • Candida parapsilosis
  • Deracemisation
  • Mechanism
  • β-Hydroxy esters

Fingerprint Dive into the research topics of 'Deracemisation of β-hydroxy esters using immobilised whole cells of Candida parapsilosis ATCC 7330: substrate specificity and mechanistic investigation'. Together they form a unique fingerprint.

Cite this