Melithiazol K
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| Category | Antibiotics |
| Catalog number | BBF-01911 |
| CAS | 248938-47-8 |
| Molecular Weight | 438.56 |
| Molecular Formula | C20H26N2O5S2 |
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Description
Melithiazol K 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.
Specification
| Synonyms | Melithiazole K |
| IUPAC Name | methyl (2Z,6E)-3,5-dimethoxy-4-methyl-7-[2-[2-(2-methyloxiran-2-yl)-4,5-dihydro-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]hepta-2,6-dienoate |
| Canonical SMILES | CC(C(C=CC1=CSC(=N1)C2CSC(=N2)C3(CO3)C)OC)C(=CC(=O)OC)OC |
| InChI | InChI=1S/C20H26N2O5S2/c1-12(16(25-4)8-17(23)26-5)15(24-3)7-6-13-9-28-18(21-13)14-10-29-19(22-14)20(2)11-27-20/h6-9,12,14-15H,10-11H2,1-5H3/b7-6+,16-8- |
| InChI Key | ZJXYLBWVBXQTFS-MZRWPZDNSA-N |
Properties
| Appearance | Oil |
| Boiling Point | 583.7±50.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. 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 ╳
