For research use only. Not for therapeutic Use.
Phomopsin A is a an acidic 13-membered cyclic hexapeptide-like metabolite with three unusual amino acids linked in an ansa macrocycle with a tripeptide tail, terminating in a dicarboxylic acid. Phomopsin A is a potent mycotoxin produced by the fungus, Phomopsis leptostromiformis, and causes lupinosis in livestock fed infected lupins. Phomopsin A is an important bioprobe for understanding cellular structural proteins.</br>Phomopsin A binds selectively to dimeric tubulin at a site overlapping that of vinblastine and maytansine, inhibiting the formation of the microtubule spindle to block cell division. Uniquely, phomopsin A protects tubulin from decay.
| Catalog Number | R003221 |
| CAS Number | 64925-80-0 |
| Synonyms | (2E)-(βS)-3-chloro-β,5-dihydroxy-N-methyl-L-tyrosyl-3,4-didehydro-L-valyl-3-hydroxy-L-isoleucyl-3,4-didehydro-L-prolyl-(2E)-2,3-didehydroisoleucyl-2,3-didehydro-aspartic acid, cyclic (1<sup>5</sup>→3)-ether |
| Molecular Formula | C36H45ClN6O12 |
| Purity | ≥95% |
| Target | Cytoskeleton |
| Solubility | Soluble in DMSO |
| Storage | -20°C |
| InChIKey | FAFRRYBYQKPKSY-MSBSFVTFSA-N |
| Reference | Structure elucidation and absolute configuration of phomopsin A, a hexapeptide mycotoxin produced by phomopsis leptostromiformis. Culvenor C. C. J. et al. , Tetrahedron 1989, 45, 2351.<br/><br/>Interaction of phomopsin A and related compounds with purified sheep brain tubulin. E. Lacey et al. , Biochem. Pharmacol. 1987, 36, 2133.<br/><br/> Interaction of phomopsin A with normal and subtilisin-treated bovine brain tubulin. Chaudhuri AR and Ludueña R.F., J. Prot. Chem. 1997, 16, 99.</span></p> |
