Melithiazol B
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| Category | Antibiotics |
| Catalog number | BBF-01907 |
| CAS | 170894-31-2 |
| Molecular Weight | 420.54 |
| Molecular Formula | C20H24N2O4S2 |
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Description
Melithiazol B 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 and cytotoxic agent.
Specification
| Synonyms | Melithiazole B |
| IUPAC Name | methyl (2E,4R,5S,6E)-3,5-dimethoxy-4-methyl-7-[2-(2-prop-1-en-2-yl-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]hepta-2,6-dienoate |
| Canonical SMILES | CC(C(C=CC1=CSC(=N1)C2=CSC(=N2)C(=C)C)OC)C(=CC(=O)OC)OC |
| InChI | InChI=1S/C20H24N2O4S2/c1-12(2)19-22-15(11-28-19)20-21-14(10-27-20)7-8-16(24-4)13(3)17(25-5)9-18(23)26-6/h7-11,13,16H,1H2,2-6H3/b8-7+,17-9+/t13-,16+/m1/s1 |
| InChI Key | MIUFOGFASQSNPX-ZVJWTWILSA-N |
Properties
| Appearance | Oil |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 587.1±60.0°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. Concise syntheses of cystothiazoles A, C, D, and melithiazol B
Yuki Iwaki, Hiroyuki Akita Chem Pharm Bull (Tokyo). 2007 Nov;55(11):1610-4. doi: 10.1248/cpb.55.1610.
A convergent synthesis of cystothiazoles C 1 and D 3 was achieved based on Julia coupling between the functionalized aldehyde 5b, corresponding to left half of the final molecule, and aryl sulfone 6 or 7, bearing a bithiazole moiety, corresponding to right half. Methylation of 1 and 3 gave cystothiazole A 2 and melithiazol B 4, respectively. The overall yield (5 steps from (2R,3S)-3-methylpent-4-yne-1,2-diol 10; 57%) of 5b via the present route was improved in comparison to that of the previously reported functionalized aldehyde 5a (7 steps from 10; 13%). By applying the modified Julia coupling method, selectivity (6E/6Z=20 : 1-26 : 1) toward the (6E)-form of the coupled products (15 or 19) against the corresponding (6Z)-form was improved in comparison to the Wittig method (6E/6Z=4 : 1-6.9 : 1).
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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 ╳
