Total Synthesis and Determination of the Absolute Configuration of Shodoamide C: An Amphotericin B Potentiator against <i>Candida albicans</i>

The total synthesis and structural determination of shodoamide C (<b>1</b>), a compound that enhances the activity of amphotericin B against <i>Candida albicans</i>, have been achieved. A synthetic strategy for compound <b>1</b> facilitated the efficient synthesis of all 16 stereoisomers, allowing for the identification of the four previously unknown stereocenters of <b>1</b> through the chiral recycle HPLC analyses. All stereoisomers of <b>1</b> showed similar activity, indicating that their stereochemistries minimally influenced it.

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Publication Details

Journal
Organic Letters
Published
2025-04-02
DOI
https://doi.org/10.1021/acs.orglett.5c01017
Citations
1
Primary Topic
Antifungal resistance and susceptibility
Type
article
Field-Weighted Citation Impact
1.40
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Total Synthesis and Determination of the Absolute Configuration of Shodoamide C: An Amphotericin B Potentiator against Candida albicans

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Total Synthesis and Determination of the Absolute Configuration of Shodoamide C: An Amphotericin B Potentiator against Candida albicans

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article en
1 citations

Abstract

The total synthesis and structural determination of shodoamide C (<b>1</b>), a compound that enhances the activity of amphotericin B against <i>Candida albicans</i>, have been achieved. A synthetic strategy for compound <b>1</b> facilitated the efficient synthesis of all 16 stereoisomers, allowing for the identification of the four previously unknown stereocenters of <b>1</b> through the chiral recycle HPLC analyses. All stereoisomers of <b>1</b> showed similar activity, indicating that their stereochemistries minimally influenced it.

Organic LettersVol. 27(14)
Kitasato University (JP), Tohoku Medical and Pharmaceutical University (JP), Komatsu (Japan) (JP)
Zero hunger
Openalex Percentile: Top 22%
Antifungal resistance and susceptibility
1.40
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