Melithiazol C
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| Category | Antibiotics |
| Catalog number | BBF-01908 |
| CAS | 214420-47-0 |
| Molecular Weight | 339.41 |
| Molecular Formula | C16H21NO5S |
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Description
Melithiazol C is an antibiotic produced by Melittangium lichenicila Mel26, Archangium gephyra Ar 7747 and Myxococcus stipitatus Mx s 64. It is a β-methoxyacrylate (MOA) inhibitor with strong anti-agent activity. Antifungal agent.
Specification
| Synonyms | Melithiazole C; Melithiazol-C |
| IUPAC Name | methyl (2E,4R,5S,6E)-7-(2-acetyl-1,3-thiazol-4-yl)-3,5-dimethoxy-4-methylhepta-2,6-dienoate |
| Canonical SMILES | CC(C(C=CC1=CSC(=N1)C(=O)C)OC)C(=CC(=O)OC)OC |
| InChI | InChI=1S/C16H21NO5S/c1-10(14(21-4)8-15(19)22-5)13(20-3)7-6-12-9-23-16(17-12)11(2)18/h6-10,13H,1-5H3/b7-6+,14-8+/t10-,13+/m1/s1 |
| InChI Key | LTTPICLGJAXUOJ-NSTYSWHMSA-N |
Properties
| Appearance | Oil |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 485.7±55.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Melithiazols, new beta-methoxyacrylate inhibitors of the respiratory chain isolated from myxobacteria. Production, isolation, physico-chemical and biological properties
F Sasse, B Böhlendorf, M Herrmann, B Kunze, E Forche, H Steinmetz, G Höfle, H Reichenbach J Antibiot (Tokyo). 1999 Aug;52(8):721-9. doi: 10.7164/antibiotics.52.721.
New antibiotic compounds, melithiazols, were isolated from the culture broth of strains of the myxobacteria Melittangium lichenicola, Archangium gephyra, and Myxococcus stipitatus. The compounds belong to the group of beta-methoxyacrylate (MOA) inhibitors and are related to the myxothiazols. The melithiazols show high antifungal activity, but are less toxic than myxothiazol A and its methyl ester in a growth inhibition assay with mouse cell cultures. The melithiazols inhibit NADH oxidation by submitochondrial particles from beef heart. Melithiazol A blocks the electron transport within the bc1-segment (complex III) and causes a red shift in the reduced spectrum of cytochrome b.
2. A concise total synthesis of melithiazole C
Julian Gebauer, Stellios Arseniyadis, Janine Cossy Org Lett. 2007 Aug 16;9(17):3425-7. doi: 10.1021/ol701459j. Epub 2007 Jul 18.
A short and convergent synthesis of the myxobacterial antibiotic melithiazole C is described featuring a highly E-selective cross-metathesis as the key step.
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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 ╳
