Melithiazol I
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| Category | Antibiotics |
| Catalog number | BBF-01910 |
| CAS | 248938-52-5 |
| Molecular Weight | 436.59 |
| Molecular Formula | C21H28N2O4S2 |
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Description
Melithiazol I 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
| IUPAC Name | methyl (2E,6E)-3,5-dimethoxy-4-methyl-7-[2-[2-(2-methylpropyl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]hepta-2,6-dienoate |
| Canonical SMILES | CC(C)CC1=NC(=CS1)C2=NC(=CS2)C=CC(C(C)C(=CC(=O)OC)OC)OC |
| InChI | InChI=1S/C21H28N2O4S2/c1-13(2)9-19-23-16(12-28-19)21-22-15(11-29-21)7-8-17(25-4)14(3)18(26-5)10-20(24)27-6/h7-8,10-14,17H,9H2,1-6H3/b8-7+,18-10+ |
| InChI Key | IREIUZIQIGYVOY-SAWMHMBASA-N |
Properties
| Appearance | Oil |
| Boiling Point | 575.1±60.0°C at 760 mmHg |
| Density | 1.2±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).
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.
3. Novel Methoxymethacrylate Natural Products Uncovered by Statistics-Based Mining of the Myxococcus fulvus Secondary Metabolome
Fabian Panter, Daniel Krug, Rolf Müller ACS Chem Biol. 2019 Jan 18;14(1):88-98. doi: 10.1021/acschembio.8b00948. Epub 2019 Jan 2.
This study reports the uncovering of new myxobacterial natural products through comprehensive analysis of the Myxococcus fulvus secondary metabolome. Statistics-based mining of mass spectrometry data paved the way for full structure elucidation of two new secondary metabolites named fulvuthiacene A and B, and investigation of the underlying biosynthetic pathway revealed an evolutionary link between the fulvuthiacene hybrid polyketide synthase (PKS) and nonribosomal peptide synthetase (NRPS) gene cluster and the related myxothiazol and melithiazol assembly lines. Detailed characterization of the post-PKS modification enzyme cascade responsible for the fulvuthiacenes' terminal β-methoxy-methyl acrylate moiety was pursued by heterologous expression of these enzymes in the myxothiazol producer Stigmatella aurantiaca DW4/3-1. The discovery of fulvuthiacenes provides new insights into the overall structure-activity relationship picture for the β-methoxyacrylate class of respiratory chain inhibitors and might thus serve as starting point for the development of next-generation β-methoxymethacrylate fungicides.
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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 ╳
