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045186 (R,R)-Hymeglusin (1233A, F-244, L-659-699) CAS: 29066-42-0

Specifications
References
CAS Number
29066-42-0
Grade
Highly Purified
MDL Number
MFCD01940046
Molecular Formula
C₁₈H₂₈O₅
Molecular Weight
324.4
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
4°C/-20°C
(2E,4E,7R)-11-[(2R,3R)-3-(Hydroxymethyl)-4-oxo-2-oxetanyl]-3,5,7-trimethyl-2,4-undecadienoic Acid; (+)-F-(244); Antibiotic 1233A; Antibiotic F 244; F 244; Hymeglusin; L 659699; [2R-[2α(2E,4E,7R*),3β]]-11-[3-(Hydroxymethyl)-4-oxo-2-oxetanyl]-3,5,7-trimethyl-2,4-undecadienoic Acid

beta-Lactone antibiotic. Antibacterial and antifungal. Specific and irreversible inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase in vitro and in vivo by covalently modifying the active Cys129 residue of the enzyme. Mevalonate biosynthesis inhibitor.

Source
Isolated from fungal strain Scopulariopsis sp. F-244.
Synonyms
(2E,4E,7R)-11-[(2R,3R)-3-(Hydroxymethyl)-4-oxo-2-oxetanyl]-3,5,7-trimethyl-2,4-undecadienoic Acid; (+)-F-(244); Antibiotic 1233A; Antibiotic F 244; F 244; Hymeglusin; L 659699; [2R-[2α(2E,4E,7R*),3β]]-11-[3-(Hydroxymethyl)-4-oxo-2-oxetanyl]-3,5,7-trimethyl-2,4-undecadienoic Acid
CAS No
29066-42-0
Molecular Weight
324.4
Molecular Formula
C₁₈H₂₈O₅
Appearance
White to off-white solid
Purity
≥95% (HPLC)
Solubility
Soluble in methanol, ethanol, DMSO, chloroform or ethyl acetate. Insoluble in water or hexane.
Storage and Stability
Store at 4°C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
References
●Antibiotic 1233A: a fungal beta-lactone: D.C. Aldridge, et al.; J. Chem. Soc. 23, 3888 (1971)|●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. (Tokyo)40, 1356 (1987)|●F-244 specifically inhibits 3-hydroxy-3-methylglutaryl coenzyme A synthase: H. Tomoda, et al.; Biochim. Biophys. Acta 922, 351 (1987)|●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. (Tokyo) 41, 247 (1988)|●Method of search for microbial inhibitors of mevalonate biosynthesis using animal cells: H. Kumagai, et al.; J. Antibiot. (Tokyo) 43, 397 (1990)|●Specific binding of beta-lactone 1233A to 3-hydroxy-3-methylglutaryl-coenzyme A synthase: H. Tomoda, et al.; J. Antibiot. (Tokyo) 46, 872 (1993)|●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)|●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)
USBio References
No references available
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