(R,R)-Hymeglusin (CAS: 29066-42-0)

C₁₈H₂₈O₅

• β-Lactone antibiotic [1].
• Antibacterial and antifungal [1, 4].
• 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 [2-4, 6-8].
• Mevalonate biosynthesis inhibitor [5].

1. Antibiotic 1233A: a fungal beta-lactone: D.C. Aldridge, et al.; J. Chem. Soc. 23, 3888 (1971)
2. 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)
3. F-244 specifically inhibits 3-hydroxy-3-methylglutaryl coenzyme A synthase: H. Tomoda, et al.; Biochim. Biophys. Acta 922, 351 (1987)
4. 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)
5. Method of search for microbial inhibitors of mevalonate biosynthesis using animal cells: H. Kumagai, et al.; J. Antibiot. (Tokyo) 43, 397 (1990)
6. Specific binding of beta-lactone 1233A to 3-hydroxy-3-methylglutaryl-coenzyme A synthase: H. Tomoda, et al.; J. Antibiot. (Tokyo) 46, 872 (1993)
7. 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)
8. 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)