2. Academic Validation
  3. Anomalous microbial transformations on the taxane ring of 10-DAB by a strain of the fungus Curvularia lunata: transbenzoylation, transacetylation, and opening of the oxetane ring

Anomalous microbial transformations on the taxane ring of 10-DAB by a strain of the fungus Curvularia lunata: transbenzoylation, transacetylation, and opening of the oxetane ring

  • J Nat Prod. 2009 Nov;72(11):2000-4. doi: 10.1021/np900368u.
Alberto Arnone 1,  Adriana Bava,  Giovanni Fronza,  Gianluca Nasini
Affiliations

Affiliation

  • 1 CNR-ICRM, Department of Chemistry, Materials and Chemical Engineering, Politecnico di Milano, via Mancinelli, 7, 20131, Milano, Italy.
PMID: 19845390 DOI: 10.1021/np900368u
Abstract

The fermentation of 10-deacetylbaccatin III (10-DAB) (1) with Curvularia lunata afforded the taxane hemiacetals 2a and 3, characterized by extensive structural modification, including C-2 to C-1 transbenzoylation, oxidation of the C-2 hydroxyl, formation of a C-9/C13 hemiacetal, epimerization at C-10, and migration of the endocyclic double bond to an exocyclic location. In compound 3, an acetate-assisted opening of the oxetane ring was also observed.

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