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Synthesis and Biophysical Studies on 35-Deoxy Amphotericin B Methyl Ester

Authors :
Erick M. Carreira
Alex M. Szpilman
Jeffrey M. Manthorpe
Nicholas R. Wurtz
Damiano M. Cereghetti
Source :
Chemistry - A European Journal. 15:7117-7128
Publication Year :
2009
Publisher :
Wiley, 2009.

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.

Details

ISSN :
09476539
Volume :
15
Database :
OpenAIRE
Journal :
Chemistry - A European Journal
Accession number :
edsair.doi.dedup.....5b2e59591ccbced3136d9160b1109abb
Full Text :
https://doi.org/10.1002/chem.200900231