Cyrmenin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01129 |
| CAS | 675150-03-5 |
| Molecular Weight | 406.51 |
| Molecular Formula | C22H34N2O5 |
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Description
It is produced by the strain of Cystobacter armeniaca Cb a24, Archangium gephyra Ar 9944. It is a β-methoxy acrylic acid (MOA) inhibitor. Cyrmenin A inhibits NADH oxidation of bovine heart submitochondrial particles with IC50 of 27 ng/mL. The mechanism is to block the bc1 phase of electron transport in the respiratory chain.
Specification
| IUPAC Name | methyl (Z)-2-[2-[[(2E,4Z)-2,11-dimethyldodeca-2,4-dienoyl]amino]prop-2-enoylamino]-3-methoxyprop-2-enoate |
| Canonical SMILES | CC(C)CCCCCC=CC=C(C)C(=O)NC(=C)C(=O)NC(=COC)C(=O)OC |
| InChI | InChI=1S/C22H34N2O5/c1-16(2)13-11-9-7-8-10-12-14-17(3)20(25)23-18(4)21(26)24-19(15-28-5)22(27)29-6/h10,12,14-16H,4,7-9,11,13H2,1-3,5-6H3,(H,23,25)(H,24,26)/b12-10-,17-14+,19-15- |
| InChI Key | VCWYTXXFJMLXBV-PBYGZRPHSA-N |
Properties
| Appearance | Oily Matter |
| Antibiotic Activity Spectrum | Fungi |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Cyrmenins, new beta-methoxyacrylate inhibitors of the electron transport. Production, isolation, physico-chemical and biological properties
Florenz Sasse, Thomas Leibold, Brigitte Kunze, Gerhard Höfle, Hans Reichenbach J Antibiot (Tokyo). 2003 Oct;56(10):827-31. doi: 10.7164/antibiotics.56.827.
New antibiotic compounds, named cyrmenins, were isolated from the culture broth of strains of the myxobacteria Cystobacter armeniaca and Archangium gephyra. The compounds belong to the group of beta-methoxyacrylate (MOA) inhibitors and are the first naturally occuring nitrogen-linked MOAs. The cyrmenins show nearly the same antifungal activity as strobilurin A, but are less toxic in a growth inhibition assay with L929 mouse cells. Cyrmenins inhibit NADH oxidation by submitochondrial particles from beef heart. Investigations by difference spectroscopy showed that cyrmenin B1 blocks the electron transport within the cytochrome bc1-segment (complex III) of the respiratory chain.
2. First total synthesis of cyrmenin B1
Narayan S Chakor, Loana Musso, Sabrina Dallavalle J Org Chem. 2009 Jan 16;74(2):844-9. doi: 10.1021/jo802209m.
A short and efficient synthesis of cyrmenin B(1), an antifungal metabolite of myxobacteria Cystobacter armeniaca and Archangium gephyra, is described. The crucial steps of the synthesis included the formation of the dehydroalanine moiety from the corresponding serine acetate and the formation of the beta-methoxyacrylate system via trimethylsilyldiazomethane methylation of the corresponding beta-hydroxy enamide.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
