Specific and irreversible inhibitor of HMG-CoA synthase in vitro and in vivo. Inhibits mevalonate biosynthesis. Shows antimicrobial and antifungal activity.
Product Details
| Alternative Name: | 1233A, F-244, (2E,4E,7R)-11-[(2R,3R)-3-(Hydroxymethyl)-4-oxooxetan-2-yl]-3,5,7-trimethylundeca-2,4-dienoic acid |
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| Formula: | C18H28O5 |
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| MW: | 324.4 |
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| Source: | Isolated from fungal strain Scopulariopsis sp. F-244. |
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| CAS: | 29066-42-0 |
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| Purity: | ≥95% (HPLC) |
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| Appearance: | White to off-white amorphous solid. |
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| Solubility: | Soluble in methanol, 100% ethanol, ethyl acetate, acetonitrile or DMSO; insoluble in water or hexane. |
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| Shipping: | Ambient |
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| Long Term Storage: | -20°C |
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| Regulatory Status: | RUO - Research Use Only |
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| Manufacturer: | Fungal strain courtesy of the Kitasato Institute, Tokyo. |
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Product Literature References
Binding site for fungal beta-lactone hymeglusin on cytosolic 3-hydroxy-3-methylglutaryl coenzyme A synthase: H. Tomoda, et al.; Biochim. Biophys. Acta
1636, 22 (2004),
Abstract;
Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitors: 2-oxetanones with a side chain mimicking the folded structure of 1233A: H. Hashizume, et al.; Chem. Pharm. Bull.
42, 512 (1994),
Abstract;
Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl-CoA synthase inhibitors: 2-oxetanones with a meta-substituent on the benzene ring in the side chain: H. Hashizume, et al.; Chem. Pharm. Bull.
42, 1272 (1994),
Abstract;
Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl-CoA synthase inhibitors: 2-oxetanones with a side chain mimicking the extended structure of 1233A: H. Hashizume, et al.; Chem. Pharm. Bull.
42, 2097 (1994),
Abstract;
Inhibition of hepatic cholesterol biosynthesis by a 3-hydroxy-3-methylglutaryl coenzyme A synthase inhibitor, 1233A, in mice: H. Nagashima, et al.; Life Sci.
52, 1595 (1993),
Abstract;
Specific binding of beta-lactone 1233A to 3-hydroxy-3-methylglutaryl-coenzyme A synthase: H. Tomoda, et al.; J. Antibiot.
46, 872 (1993),
Abstract;
Biosynthesis of antibiotic 1233A (F-244) and preparation of [14C]1233A: H. Kumagai, et al.; J. Antibiot.
45, 563 (1992),
Abstract;
Synthesis of 1233A analogs and their inhibitory activity against hydroxymethylglutaryl coenzyme A synthase: T. Sunazuka, et al.; J. Antibiot.
45, 1139 (1992),
Abstract;
Method of search for microbial inhibitors of mevalonate biosynthesis using animal cells: H. Kumagai, et al.; J. Antibiot.
43, 397 (1990),
Abstract;
F-244 (1233A), a specific inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A synthase: taxonomy of producing strain, fermentation, isolation and biological properties: H. Tomoda, et al.; J. Antibiot.
41, 247 (1988),
Abstract;
F-244 specifically inhibits 3-hydroxy-3-methylglutaryl coenzyme A synthase: H. Tomoda, et al.; Biochim. Biophys. Acta
922, 351 (1987),
Abstract;
Potent inhibitory effect of antibiotic 1233A on cholesterol biosynthesis which specifically blocks 3-hydroxy-3-methylglutaryl coenzyme A synthase: S. Omura, et al.; J. Antibiot.
40, 1356 (1987),
Abstract;
Antibiotic 1233A: a fungal -lactone: D.C. Aldridge, et al.; J. Chem. Soc.
23, 3888 (1971),
Abstract;
