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Echinocandin B
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IUPAC name
(9Z,12Z)-N-{(2R,6S,9R,11R,12R,14aS,16R,20S,23S,25aS)-23-[(1S,2S)-1,2-Dihydroxy-2-(4-hydroxyphenyl)ethyl]-2,11,12-trihydroxy-6,20-bis[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l] [1,4,7,10,13,16]hexaazacyclohenicosin-9-yl}-9,12-octadecadienamide
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Identifiers | |
3D model (JSmol)
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ChemSpider |
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ECHA InfoCard | 100.184.852 |
MeSH | echinocandin+B |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C52H81N7O16 | |
Molar mass | 1060.24 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Echinocandin B, a lipopeptide, is a naturally occurring cyclic hexapeptide with a linoleoyl side chain. It belongs to a class of antifungal agents called echinocandins, which inhibits the synthesis of glucan, a major component of the fungal cell wall, via noncompetitive inhibition of a crucial enzyme, β-(1→3)-D-glucan synthase. Echinocandin B is a fermentation product of Aspergillus nidulans and the closely related species, A. rugulosus; discovered in 1974 in A. nidulans var. echinulatus strain A 32204 in Germany, it was the first of the echinocandin class of antifungals.
Echinocandin B can undergo deacylation (removal of the lipid side chain) by the action of a deacylase enzyme from the filamentous bacterium Actinoplanes utahensis, which catalyzes the cleavage of the linoleoyl side chain; in three subsequent synthetic steps, including a chemical reacylation, the antifungal drug anidulafungin is synthesized.
External links
- Media related to Echinocandin B at Wikimedia Commons