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P3970 Phomopsin A CAS: 64925-80-0

Specifications
References
CAS Number
64925-80-0
Grade
Highly Purified
Molecular Formula
C36H45ClN6O12
Molecular Weight
789.2
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
-20°C
2-Oxa-5,8-diazabicyclo[10.3.1]hexadecane, cyclic peptide deriv.; 3-Chloro-erythro-β,5-dihydroxy-N-methyl-L-tyrosyl-3,4-didehydro-L-valyl-3-hydroxy-L-isoleucyl-3,4-didehydro-L-prolyl-(E)-2,3-didehydroisoleucyl-(E)-2,3-didehydroaspartic acid cyclic (15→3)-ether; NSC 381839

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.

Source
Phomposis leptostromiformis MST-FP2068
Solubility
Soluble in ethanol, methanol, DMF or DMSO. Slightly soluble in water.
Storage and Stability
May be stored at RT for short-term only. Long-term storage is recommended at -20°C. Stable for 6 months at -20°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
References
1. 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. 2. Interaction of phomopsin A and related compounds with purified sheep brain tubulin. E. Lacey et al., Biochem. Pharmacol. 1987, 36, 2133. 3. Interaction of phomopsin A with normal and subtilisin-treated bovine brain tubulin. Chaudhuri AR and Ludueña R.F., J. Prot. Chem. 1997, 16, 99.
USBio References
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