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

Name: (R,R)-Hymeglusin [29066-42-0]
SKU: AG-CN2-0103_A27
Price: 173 EUR
Availability: BackOrder

AG-CN2-0103

CAS Number29066-42-0

Product group Chemicals

Estimated Purity>95%

Molecular Weight324.4

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
2°C to 8°C,-20°C
UNSPSC
12352200

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)