title: Synthesis and biophysical studies on 35-deoxy amphotericin B methyl ester.
abstract: 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 mycosamine 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.
authors: Laboratorium für Organische Chemie der ETH-Zürich, HCI H 335, Wolfgang Pauli Strasse 10, 8093 Zurich, Switzerland.
authors: Alex M
authors: AM
authors: Szpilman
authors: Damiano M
authors: DM
authors: Cereghetti
authors: Jeffrey M
authors: JM
authors: Manthorpe
authors: Nicholas R
authors: NR
authors: Wurtz
authors: Erick M
authors: EM
authors: Carreira
mesh_terms: D000666:Amphotericin B / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D055592:Biophysical Phenomena; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry; D006595:Hexosamines / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D006027:Glycosides; D006595:Hexosamines; C017501:methylamphotericin B; C014692:mycosamine; D000666:Amphotericin B