PHOMOPSIN A
- CAS No.
- 64925-80-0
- Chemical Name:
- PHOMOPSIN A
- Synonyms
- PMSA;phomopsin;PHOMOPSIN A;phomopsin a from phomopsis leptostromiformis;Phomopsin A, 98%, from Phomopsis leptostromiformis;Aspartic acid, (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-, cyclic (15→3)-ether, (2E)-
- CBNumber:
- CB9359240
- Molecular Formula:
- C36H45ClN6O12
- Molecular Weight:
- 789.23
- MOL File:
- 64925-80-0.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/6/8 9:02:40
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P280-P302+P352-P362+P364 | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 20/21/22-40 | |||||||||
| Safety Statements | 36/37/39 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | SY2593000 | |||||||||
| HS Code | 2941900000 | |||||||||
| NFPA 704 |
|
PHOMOPSIN A Chemical Properties,Uses,Production
Uses
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. It 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.
Enzyme inhibitor
This mycotoxin and antibiotic (FW = 789.24 g/mol; CAS 64925-80-0) is obtained from Diaporthe toxica (formerly Phomopsis leptostromiformis), a fungus that grows mainly within lupin stems, the consumption of which leads to lupinosis in sheep grazing on lupin stubble. Intoxication results in liver damage, disorientation, blindness, lethargy and death in severe cases. Phomopsin A is a 13-membered ether oxygen-containing macrolide that blocks tubulin polymerization (Ki <1 μM). It also inhibits vinblastine binding to tubulin and, in common with vinblastine and maytansine, enhances colchicine binding. Phomopsin A and the depsipeptide, Dolastatin 10, bind to a site adjacent to the vinca alkaloid and nucleotide sites. This mycotoxin induces tubulin oligomerization into ring structures that cannot form microtubules. Scatchard analysis suggests two classes of binding sites: a high-affinity site (K1 = 1 x 10–8 M) and a low-affinity site (K2 = 3 x 10–7 M). Phomopsin A also inhibits rhizoxin binding, with a Ki of 0.8 x 10–8 M, suggesting that the high-affinity site of phomopsin A is identical to the rhizoxin binding site. The development and validation of an LC-MS/MS method for detecting Phomopsin A in lupin and lupincontaining retail food has been reported.
PHOMOPSIN A Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | United States | 32080 | 58 | Inquiry |
| BOC Sciences | 16314854226; +16314854226 | United States | 19741 | 58 | Inquiry |
| Aladdin Scientific | +1-+1(833)-552-7181 | United States | 52925 | 58 | Inquiry |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | China | 9806 | 58 | Inquiry |
| Cayman Chemical Company | (800) 364-9897 | United States | 6213 | 81 | Inquiry |
| EMD Biosciences, Inc. | 858 450 5500 | United States | 6529 | 66 | Inquiry |
| BIOMOL INTERNATIONAL, LP | (800) 942-0430 | United States | 1499 | 77 | Inquiry |
| 3B Scientific Corporation | 847.281.9822 | United States | 6718 | 47 | Inquiry |
| 2A PharmaChem USA | (630) 737-0988 | United States | 6137 | 39 | Inquiry |
| Leancare Ltd. | +33 962096793 | United Kingdom | 6446 | 42 | Inquiry |
| Supplier | Advantage |
|---|---|
| TargetMol Chemicals Inc. | 58 |
| BOC Sciences | 58 |
| Aladdin Scientific | 58 |
| Shanghai EFE Biological Technology Co., Ltd. | 58 |
| Cayman Chemical Company | 81 |
| EMD Biosciences, Inc. | 66 |
| BIOMOL INTERNATIONAL, LP | 77 |
| 3B Scientific Corporation | 47 |
| 2A PharmaChem USA | 39 |
| Leancare Ltd. | 42 |
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