Date published: 2026-6-21

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Cladospirone bisepoxide (CAS 155866-40-3)

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Alternate Names:
(1ar,6s,7s,7ar)-6,7-dihydroxy-7,7a-dihydro-1ah-spiro[2a,6a-epoxynaphtho[2,3-b]oxirene-2,2′-naphtho[1,8-de][1,3]dioxin]-3(6h)-one
Application:
Cladospirone bisepoxide is a selective antifungal and antimicrobial agent
CAS Number:
155866-40-3
Molecular Weight:
366.32
Molecular Formula:
C20H14O7
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Cladospirone bisepoxide, registered under CAS number 155866-40-3, is a bioactive chemical compound known for its unique bisepoxide structure which plays a central role in its interaction with biological molecules. This compound is a member of the spiroketals, a class of organic compounds characterized by their spiroketal ring systems, where two carbon rings are joined through a single shared atom. Cladospirone bisepoxide′s mechanism of action is primarily associated with its ability to form covalent bonds with nucleophilic sites in biomolecules due to its epoxide groups. These reactive epoxide groups can undergo ring-opening reactions when encountering nucleophilic amino acids in proteins, potentially leading to the modification of protein function or the inhibition of enzymatic activity. In research, Cladospirone bisepoxide has been utilized as a molecular probe to study protein-epoxide interactions, helping to identify critical nucleophilic sites within proteins and to understand the structural basis of protein modification by epoxides. This research is crucial for elucidating the pathways through which epoxide-containing compounds exert their biological effects, and it aids in the design of molecular tools and inhibitors based on epoxide reactivity. Moreover, studies involving Cladospirone bisepoxide contribute to broader scientific understanding of the biotransformation and detoxification processes of epoxide compounds in biological systems.


Cladospirone bisepoxide (CAS 155866-40-3) References

  1. Biosynthesis of cladospirone bisepoxide, a member of the spirobisnaphthalene family.  |  Bode, HB., et al. 2000. J Antibiot (Tokyo). 53: 153-7. PMID: 10805575
  2. UV mutagenesis and enzyme inhibitors as tools to elucidate the late biosynthesis of the spirobisnaphthalenes.  |  Bode, HB. and Zeeck, A. 2000. Phytochemistry. 55: 311-6. PMID: 11117878
  3. Big effects from small changes: possible ways to explore nature's chemical diversity.  |  Bode, HB., et al. 2002. Chembiochem. 3: 619-27. PMID: 12324995
  4. Spirobisnaphthalenes from fungi and their biological activities.  |  Zhou, L., et al. 2010. Mini Rev Med Chem. 10: 977-89. PMID: 20491650
  5. Structure, bioactivities, biosynthetic relationships and chemical synthesis of the spirodioxynaphthalenes.  |  Cai, YS., et al. 2010. Nat Prod Rep. 27: 1840-70. PMID: 21038061
  6. Induction of New Aromatic Polyketides from the Marine Actinobacterium Streptomyces griseorubiginosus through an OSMAC Approach.  |  Martín-Aragón, VR., et al. 2023. Mar Drugs. 21: PMID: 37888461
  7. Production of cladospirone bisepoxide, a new fungal metabolite.  |  Petersen, F., et al. 1994. J Antibiot (Tokyo). 47: 1098-103. PMID: 7961158
  8. Cladospirone bisepoxide: Definite structure assignment including absolute configuration and selective chemical transformations  |  Thiergardt, R., et al. 1995. Tetrahedron. 51(3): 733-742.
  9. Syntheses of palmarumycin CP1 and CP2, CJ-12,371 and novel analogues  |  Ragot, J. P., et al. 1998. Tetrahedron letters. 39(27): 4921-4924.
  10. Biosynthesis of spiro-mamakone A, a structurally unprecedented fungal metabolite  |  van der Sar, S. A., Lang, G., Mitova, M. I., Blunt, J. W., Cole, A. L., Cummings, N.,.. & Munro, M. H. 2008. The Journal of Organic Chemistry. 73(21): 8635-8638.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Cladospirone bisepoxide, 1 mg

sc-202546
1 mg
$210.00

Cladospirone bisepoxide, 5 mg

sc-202546A
5 mg
$930.00