Synthesis and biophysical studies on 35-Deoxy amphotericin b methyl ester

Alex M. Szpilman, Damiano M. Cereghetti, Jeffrey M. Manthorpe, Nicholas R. Wurtz, Erick M. Carreira

Research output: Contribution to journalArticlepeer-review

39 Scopus citations


The use of molecular editing in the elucidation of the mechanism of action of amphotericin B is presented. A modular strategy for the synthesis of amphotericin B and its designed analogues is developed, which relies on an efficient gram-scale synthesis of various subunits of amphotericin B. A novel method for the coupling of the mycosa-mine to the aglycone was identified. The implementation of the approach has enabled the preparation of 35-deoxy amphotericin B methyl ester. Investigation of the antifungal activity and efflux-inducing ability of this amphotericin B congener provided new clues to the role of the 35-hydroxy group and is consistent with the involvement of double barrel ion channels in causing electrolyte efflux. 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

Original languageEnglish
Pages (from-to)7117-7128
Number of pages12
JournalChemistry - A European Journal
Issue number29
StatePublished - 20 Jul 2009
Externally publishedYes


  • Amphotericin b
  • Antifungal agents
  • Natural products
  • Structure-activity relationship
  • Total synthesis


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