| Identification | Back Directory | [Name]
Basifungin | [CAS]
127785-64-2 | [Synonyms]
LY-295337
Basifungin
aureobasidin A
Aureobasidin A (9CI)
Aureobasidin A (AbA)
Basifungin/Aureobasidin A
Basifungin ISO 9001：2015 REACH
Cyclo[L-Phe-N-methyl-L-Phe-L-Pro-L-aIle-N-methyl-L-Val-L-Leu-N-methyl-β-hydroxy-L-Val-[(3R)-D-Hmp-]-N-methyl-L-Val-]
Cyclo[L-alloisoleucyl-N-methyl-L-valyl-L-leucyl-N,3-dimethyl-L-threonyl-(2R,3R)-2-hydroxy-3-methylpentanoyl-N-methyl-L-valyl-L-phenylalanyl-N-methyl-L-phenylalanyl-L-prolyl] | [Molecular Formula]
C60H92N8O11 | [MDL Number]
MFCD01675341 | [MOL File]
127785-64-2.mol | [Molecular Weight]
1101.43 |
| Chemical Properties | Back Directory | [Boiling point ]
1229.1±65.0 °C(Predicted) | [density ]
1.19±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C, protect from light | [solubility ]
DMSO : 100 mg/mL (90.79 mM; Need ultrasonic) | [pka]
13.35±0.70(Predicted) |
| Hazard Information | Back Directory | [Uses]
Antifungal. | [Definition]
ChEBI: A cyclodepsipeptide antibiotic, which is isolated from the filamentous fungus Aureobasidium pullulans R106 and is toxic to yeast at low concentrations (0.1-0.5 ug/ml). | [Clinical Use]
Aureobasidin A is a cyclic depsipeptide that is produced byfermentation in cultures of Aureobasidium pullulan.Aureobasidin A acts as a tight-binding noncompetitive inhibitorof the enzyme inositol phosphorylceramide synthase(IPC synthase), which is an essential enzyme for fungalsphingolipid biosynthesis. A unique structural feature of theaureobasidins is the N-methylation of four of seven amide nitrogenatoms. The lack of tautomerism dictated by N-methylationmay contribute to forming a stable solution conformerthat is shaped somewhat like an arrowhead, the presumed biologicallyactive conformation of aureobasidin-A.The pradimycins and benanomycins are naphthacenequinonesthat bind mannan in the presence of Ca2+ to disrupt the cell membrane in pathogenic fungi. Both demonstrate good in vitro and in vivo activity againstCandida spp. and C. neoformans clinical isolates. | [Enzyme inhibitor]
This cyclic depsipeptide antibiotic (FWAureosasidin-A = 1101.43; CAS 127785-
64-2) from Aureobasidium pullulans R106 is toxic (typically at 0.1-0.5
μg/mL) against Saccharomyces cerevisiae, Schizosaccharo-myces pombe,
Candida glabrata, Aspergillus nidulans, and A. niger. Aureobasdin A
inhibits inositolphosphoryl-ceramide synthase. Note that the antibiotic
contains N-methyl-L-valine, L-alloisoleucine, N-methyl-L-phenyl-alanine,
and N-methyl-3-hydroxy-L-valine. Target (s) : inositolphosphoryl-
ceramide synthase, or ceramide inositolphosphoryltransferase, inhibited by
aureobasidin A. |
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