Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-α-santalol

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DOI

  • Pankaj P Daramwar
    CSIR-National Chemical Laboratory, Pune
  • Prabhakar Lal Srivastava
    CSIR-National Chemical Laboratory, Pune
  • Swati P Kolet
    CSIR-National Chemical Laboratory, Pune
  • Hirekodathakallu V Thulasiram
    CSIR-National Chemical Laboratory, Pune

Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation on (Z)-α-santalol were achieved for the first time, using a fungal strain Mucor piriformis. Four novel metabolites were characterized as 10,11-cis-β-epoxy-α-santalol, 5α-hydroxy-(Z)-α-santalol, 10,11-dihydroxy-α-santalol and 5α-hydroxy-10,11-cis-β-epoxy-α-santalol. Using Amano PS lipase from Burkholderia cepacia, α- and β-isomers of 10,11-cis-epoxy-α-santalol were resolved efficiently.

Keywords

  • Biocatalysis, Burkholderia cepacia/enzymology, Hydroxylation, Lipase/metabolism, Molecular Conformation, Mucor/metabolism, Polycyclic Sesquiterpenes, Sesquiterpenes/metabolism, Stereoisomerism
Original languageEnglish
Pages (from-to)1048-51
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number7
DOIs
Publication statusPublished - 21 Feb 2014
Externally publishedYes
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