For Research Use Only. Not for human or veterinary use.
Aspirochlorine
Product ID: BLK-1600
Structure
CAS
59978-04-0
Molecular Formula
C12H9ClN2O5S2
Molecular Weight
360.8
UN (Transport)
UN 2811
Price
1mg: USD 360.00 / 5mg: - / 25mg: -
Storage
-20°C
Solubility
1mg/ml ethanol, methanol, DMSO
Purity
>95%
Source Organism
Aspergillus sp.
Summary
Aspirochlorine Aspergillus-derived epipolythiodioxopiperazine (ETP) that inhibits fungal protein synthesis and overcomes azole resistance.
Details
Aspirochlorine is a fungal epidithiodiketopiperazine (ETP) metabolite originally isolated from Aspergillus species. It selectively inhibits fungal protein synthesis in Candida albicans without affecting bacterial or mammalian translation systems. Aspirochlorine is active against azole-resistant Candida strains, highlighting its therapeutic potential. Structurally, it features a ring-enlarged disulfide bridge and a spiroaminal system formed through a specialized oxidoreductase-mediated sulfur migration. Its biosynthesis involves unusual peptide editing, including retro-aldol conversion of phenylalanine to glycine, expanding the chemical diversity of ETP natural products.
Mechanism
Inhibits fungal protein synthesis via ETP-mediated disruption of translation machinery.
Primary Target
Eukaryotic ribosome
Pathway
Fungal protein translation
Chemical Class
Epidithiodiketopiperazine (ETP)
Discovery Year
1999
Keywords
epidithiodiketopiperazinefungal protein synthesis inhibitorazole-resistant antifungalcandida albicans inhibitorsulfur-containing diketopiperazinespiroaminal scaffoldfungal secondary metaboliteantifungal research tool
References
Kudo Y et al., J Antibiot (Tokyo), 1999, 52:311-318