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Melithiazol C

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Melithiazol C
Category Antibiotics
Catalog number BBF-01908
CAS 214420-47-0
Molecular Weight 339.41
Molecular Formula C16H21NO5S

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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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
Appearance Oil
Antibiotic Activity Spectrum fungi
Boiling Point 485.7±55.0°C at 760 mmHg
Density 1.2±0.1 g/cm3
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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