Phomopsin A is an acidic 13-membered cyclic hexapeptide-like metabolite with three unusual amino acids linked in an "ansa" macrocycle with a three amino acid "tail", terminating in a dicarboxylic acid. Phomopsin A is a potent mycotoxin produced by the fungus Phomopsis leptostromiformis and is the causative agent of lupinosis in livestock fed infected lupins. Phomopsin A is an important bioprobe for understanding cellular structural proteins. It acts by selectively binding to dimeric tubulin, inhibiting the formation of the microtubule spindle to block cell division. Phomopsin A binds to tubulin at a site overlapping that of vinblastine and maytansine. Uniquely, phomopsin A protects tubulin from decay.
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