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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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-05, Vol.47 (23), p.4339-4342
Main Authors: Szpilman, Alex M, Manthorpe, Jeffrey M, Carreira, Erick M
Format: Article
Language:English
Subjects:
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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Summary: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