Synthesis and Biological Studies of 35-Deoxy Amphotericin B Methyl Ester

An indispensable OH group: The synthesis of 35‐deoxy amphotericin B methyl ester was completed by using a novel method for the coupling of the mycosamine to the aglycone. The investigation of the antifungal activity and efflux‐inducing ability of this compound provided data that underscore the relev...

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Veröffentlicht in:	Angewandte Chemie (International ed.) 2008-05, Vol.47 (23), p.4339-4342
Hauptverfasser:	Szpilman, Alex M, Manthorpe, Jeffrey M, Carreira, Erick M
Format:	Artikel
Sprache:	eng
Schlagworte:	Amphotericin B - analogs & derivatives amphotericin B antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - pharmacology Candida albicans - drug effects Cell Membrane - chemistry Cell Membrane - drug effects Glycosides - chemistry Hydrogen Bonding Ion Channels - chemistry mechanism of action Methods natural products Saccharomyces cerevisiae - drug effects total synthesis
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Beschreibung
Zusammenfassung:	An indispensable OH group: The synthesis of 35‐deoxy amphotericin B methyl ester was completed by using a novel method for the coupling of the mycosamine to the aglycone. The investigation of the antifungal activity and efflux‐inducing ability of this compound provided data that underscore the relevance of the hydroxy group at C35 and supports the involvement of double‐barrel ion channels.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200800590