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Antifungal Agents01:15

Antifungal Agents

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Amphotericin B is a broad-spectrum antifungal agent that exploits structural differences between fungal and mammalian cell membranes. Its amphipathic structure—featuring a hydrophobic polyene-lactone ring and a hydrophilic region containing mycosamine and carboxylic acid groups—enables selective binding to ergosterol, a sterol predominantly found in fungal plasma membranes. This selective interaction underlies the drug’s antifungal activity, although weak binding to...
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Updated: May 1, 2026

Measuring Volatile and Non-volatile Antifungal Activity of Biocontrol Products
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Total Synthesis of Verlamelin A and (5R)-Verlamelin A with Antifungal Activity.

Xin Sun1,2, Youhong Li1,2, Wenshen Lin1,2

  • 1Shenzhen Clinical College of Integrated Chinese and Western Medicine, Guangzhou University of Chinese Medicine, Shenzhen 518104, China.

The Journal of Organic Chemistry
|August 26, 2025
PubMed
Summary

The first total synthesis of antifungal compound verlamelin A and its epimer (5R)-verlamelin A was achieved. Both compounds show potent antifungal activity, with the epimer demonstrating superior efficacy against Alternaria alternate.

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Area of Science:

  • Natural Product Synthesis
  • Medicinal Chemistry
  • Antifungal Agents

Background:

  • Verlamelin A is a macrocyclic depsipeptide with broad-spectrum antifungal properties.
  • Developing efficient synthetic routes for natural products is crucial for drug discovery.

Purpose of the Study:

  • To report the first unified total synthesis of verlamelin A and its C5-epimer, (5R)-verlamelin A.
  • To evaluate the antifungal activity of the synthesized compounds.

Main Methods:

  • Homogeneous solution-phase and solid-phase peptide synthesis strategies were employed.
  • On-resin coupling, off-resin cyclization, and global deprotection were utilized.
  • Spectroscopic methods (NMR, HRMS) and HPLC confirmed the synthesis.

Main Results:

  • Successful total synthesis of verlamelin A and (5R)-verlamelin A in 6.8% and 7.8% overall yields, respectively.
  • Both compounds exhibited potent antifungal activity against Alternaria alternate, Alternaria solani, and Rhizoctonia solani (MICs 4-16 μg/mL).
  • (5R)-verlamelin A showed enhanced efficacy against Alternaria alternate (MIC = 4 μg/mL).

Conclusions:

  • The developed synthetic strategy enables access to verlamelin A and its epimer.
  • Verlamelin A and (5R)-verlamelin A are potent antifungal agents.
  • (5R)-verlamelin A is a promising lead candidate for developing new antifungal treatments.