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ProductsBack/(R,R)-Hymeglusin [29066-42-0]
Chemical Structure
Chemical Structure
Chemical Structure

(R,R)-Hymeglusin [29066-42-0]

Research Use Only
AG-CN2-0103
AdipoGen Life Sciences
CAS Number29066-42-0
DownloadMSDS
Product group Chemicals
Estimated Purity>95%
Molecular Weight324.4
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    (R,R)-Hymeglusin [29066-42-0]
  • Delivery Days Customer
    10
  • CAS Number
    29066-42-0
  • Certification
    Research Use Only
  • Estimated Purity
    >95%
  • Molecular Formula
    C18H28O5
  • Molecular Weight
    324.4
  • Scientific Description
    beta-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]. - Chemical. CAS: 29066-42-0. Formula: C18H28O5. MW: 324.4. Isolated from fungal strain Scopulariopsis sp. F-244. 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.
  • SMILES
    C[C@H](CCCC[C@H]1OC(=O)[C@@H]1CO)C\C(C)=C\C(\C)=C\C(O)=O
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

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)