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Ascomycin New

Cayman Chemical Item Number 11309

FR 900520; L 683590; FK-520; Changchuanmycin; Immunomycin (CAS 11011-38-4)

Ascomycin (CAS 11011-38-4)

Description

Ascomycin, produced by the fermentation of S. hygroscopicus ascomyceticus, is an ethyl analog of tacrolimus (FK-506) with potent immunosuppressant properties that prevents T-cell proliferation through initial binding to FK-506-binding protein 12 (FKBP12), an immunophilin that acts as the principal mediator of FK506- and rapamycin-induced immunosuppression.1,2 Ascomycin inhibits the enzymatic peptidyl-prolyl cis-trans isomerase and chaperone activities of PfFKBP35, an FKBP from P. falciparum, a causative agent of malaria in humans with an IC50 value of 0.52 μM.3

1 Mrowietz, U. Macrolide immunosuppressants. Eur J Dermatol 9(5) 346-351 (1999).

2 Andexer, J.N., Kendrew, S.G., Nur-e-Alam, M., et al. Biosynthesis of the immunosuppressants FK506, FK520, and rapamycin involves a previously undescribed family of enzymes acting on chorismate. Proc Natl Acad Sci USA 108(12) 4776-4781 (2011).

3 Monaghan, P., Fardis, M., Revill, W.P., et al. Antimalarial effects of macrolactones related to FK520 (ascomycin) are independent of the immunosuppressive properties of the compounds. J Infect Dis 191 1342-1349 (2005).

Synonyms
  • FR 900520
  • L 683590
  • FK-520
  • Changchuanmycin
  • Immunomycin
Formal Name (3S,​4R,​5S,​8R,​9E,​12S,​14S,​15R,​16S,​18R,​19R,​26aS)-​8-​ethyl-​5,​6,​8,​11,​12,​13,​14,​15,​16,​17,​18,​19,​24,​25,​26,​26a-​hexadecahydro-​5,​19-​dihydroxy-​3-​[(1E)-​2-​[(1R,​3R,​4R)-​4-​hydroxy-​3-​methoxycyclohexyl]-​1-​methylethenyl]-​14,​16-​dimethoxy-​4,​10,​12,​18-​tetramethyl-​15,​19-​epoxy-​3H-​pyrido[2,​1-​c][1,​4]oxaazacyclotricosine-​1,​7,​20,​21(4H,​23H)-​tetrone
CAS Number 11011-38-4
Molecular Formula C43H69NO12
Formula Weight 792.0
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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O=C(C(N1[C@H]​(C(O[C@@H]​([C@@H]​([C@@H]​(O)​CC([C@H]​(CC)​/C=C(C[C@H]​(C)​C[C@@H]​2OC)​\C)​=O)​C)​/C(C)​=C/[C@@H]​3CC[C@@H]​(O)​[C@H]​(OC)​C3)​=O)​CCCC1)​=O)​[C@]​4(O)​O[C@H]​2[C@@H]​(OC)​C[C@H]​4C
Size Price Quantity Subtotal
5 mg $39.00 $0.00
10 mg $74.00 $0.00
25 mg $120.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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