Cystothiazole B
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| Category | Others |
| Catalog number | BBF-01133 |
| CAS | 207399-38-0 |
| Molecular Weight | 438.56 |
| Molecular Formula | C20H26N2O5S2 |
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Description
It is produced by the strain of Cystobacter fuscus. It has no anti-bacterial effect.
Specification
| IUPAC Name | methyl (2E,4R,5S,6E)-7-[2-[2-(2-hydroxypropan-2-yl)-1,3-thiazol-4-yl]-1,3-thiazol-4-yl]-3,5-dimethoxy-4-methylhepta-2,6-dienoate |
| Canonical SMILES | CC(C(C=CC1=CSC(=N1)C2=CSC(=N2)C(C)(C)O)OC)C(=CC(=O)OC)OC |
| InChI | InChI=1S/C20H26N2O5S2/c1-12(16(26-5)9-17(23)27-6)15(25-4)8-7-13-10-28-18(21-13)14-11-29-19(22-14)20(2,3)24/h7-12,15,24H,1-6H3/b8-7+,16-9+/t12-,15+/m1/s1 |
| InChI Key | DEBRBEDKRGQAPL-RPKNRIRISA-N |
Properties
| Appearance | White Powder |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Cystothiazoles A and B, new bithiazole-type antibiotics from the myxobacterium Cystobacter fuscus
M Ojika, Y Suzuki, A Tsukamoto, Y Sakagami, R Fudou, T Yoshimura, S Yamanaka J Antibiot (Tokyo). 1998 Mar;51(3):275-81. doi: 10.7164/antibiotics.51.275.
New bithiazole-type antibiotics, cystothiazoles A (C20H26N2O4S2) and B (C20H26N2O5S2), have been isolated from a culture broth of the myxobacterium, Cystobacter fuscus. The gross structures of these compounds were elucidated by spectroscopic analysis, and their absolute stereochemistry was determined by chemical degradation of cystothiazole A. Cystothiazole A inhibits fungi and human tumor cells, whereas it is inactive against bacteria. The antifungal activity appears to result from the inhibition of submitochondrial NADH oxidation. Although these compounds are structurally related to the known antibiotic myxothiazol, cystothiazole A was more active against fungi and less cytotoxic than myxothiazol.
2. Total synthesis of cystothiazoles A and B
Jian Shao, James S Panek Org Lett. 2004 Sep 2;6(18):3083-5. doi: 10.1021/ol048893d.
[structure: see text] Convergent enantioselective syntheses of the antifungal agents cystothiazoles A and B are described. The routes feature an asymmetric crotylation using a propargylic dicobalt hexacarbonyl complex, which provided enhanced diastereoselectivity over the uncomplexed propargylic acetal. The bisthiazole fragment was united with the side chain through a Stille cross-coupling of a terminal (E)-vinylstannane with a 4-trifloyl-substituted thiazole.
3. Determination of the absolute structure of (+)-cystothiazole B
Takamitsu Sasaki, Keisuke Kato, Hiroyuki Akita Chem Pharm Bull (Tokyo). 2004 Jun;52(6):770-1. doi: 10.1248/cpb.52.770.
Palladium-catalyzed cyclization-methoxycarbonylation of (2R,3S)-3-methylpenta-4-yne-1,2-diol (6) derived from (2R,3S)-epoxy butanoate 5, followed by methylation, gave the tetrahydro-2-furylidene acetate (-)-7, which was converted to the left-half aldehyde (+)-3. A Wittig reaction between (+)-3 and the phosphoranylide derived from the bithiazole-type phosphonium iodide 4 using lithium bis(trimethylsilyl)amide afforded (+)-cystothiazole B (2), the spectral data of which were identical to those of the natural product (+)-2. Thus the stereochemistry of cystothiazole B (2) was confirmed to be [4R, 5S, 6(E)].
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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 ╳
