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 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 language | English |
|---|---|
| Pages (from-to) | 7117-7128 |
| Number of pages | 12 |
| Journal | Chemistry - A European Journal |
| Volume | 15 |
| Issue number | 29 |
| DOIs | |
| State | Published - 20 Jul 2009 |
| Externally published | Yes |
Keywords
- Amphotericin b
- Antifungal agents
- Natural products
- Structure-activity relationship
- Total synthesis
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