Molecular structure of Hymeglusin, CAS Number: 29066-42-0
Hymeglusin (CAS 29066-42-0)
See product citations (2)
Alternate Names:
11-[3R-(hydroxymethyl)-4-oxo-2R-oxetanyl]-3,5,7R-trimethyl-2E,4E-undecadienoic acid
Application:
Hymeglusin is an irreversible HMG-CoA synthase inhibitor
CAS Number:
29066-42-0
Purity:
>95%
Molecular Weight:
324.4
Molecular Formula:
C18H28O5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Hymeglusin is a fungal beta-lactone cell wall-targeting antibiotic that irreversibly inhibits cytosolic 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase by covalently modifying the active Cys 129 residue of the enzyme. Studies show that Hymeglusin can be inhibited by the (2R, 3R)-isomer of beta-lactone trans-DU-6622 because this lactone binds to the same site on HMG-CoA synthase as Hymeglusin. In addition, Hymeglusin suppresses the translation of cWRA in Staphylococcus aureus, which codes for a polypepetide that responds to cell wall inhibition.
Hymeglusin (CAS 29066-42-0) References
- Differential inhibition of HMG-CoA synthase and pancreatic lipase by the specific chiral isomers of beta-lactone DU-6622. | Tomoda, H., et al. 1999. Biochem Biophys Res Commun. 265: 536-40. PMID: 10558904
- The biosynthetic incorporation of the intact leucine skeleton into sterol by the trypanosomatid Leishmania mexicana. | Ginger, ML., et al. 2001. J Biol Chem. 276: 11674-82. PMID: 11148203
- The reversal of the inhibition on lipids synthesis by L-659,699 in arterial smooth muscle cells cultures. | Carazo, A., et al. 2001. Mol Cell Biochem. 221: 25-31. PMID: 11506182
- Binding site for fungal beta-lactone hymeglusin on cytosolic 3-hydroxy-3-methylglutaryl coenzyme A synthase. | Tomoda, H., et al. 2004. Biochim Biophys Acta. 1636: 22-8. PMID: 14984735
- cwrA, a gene that specifically responds to cell wall damage in Staphylococcus aureus. | Balibar, CJ., et al. 2010. Microbiology (Reading). 156: 1372-1383. PMID: 20167623
- Biochemical and structural basis for inhibition of Enterococcus faecalis hydroxymethylglutaryl-CoA synthase, mvaS, by hymeglusin. | Skaff, DA., et al. 2012. Biochemistry. 51: 4713-22. PMID: 22510038
- Inhibition of hydroxymethylglutaryl-coenzyme A synthase by L-659,699. | Greenspan, MD., et al. 1987. Proc Natl Acad Sci U S A. 84: 7488-92. PMID: 2890166
- HMGCS1 drives drug-resistance in acute myeloid leukemia through endoplasmic reticulum-UPR-mitochondria axis. | Zhou, C., et al. 2021. Biomed Pharmacother. 137: 111378. PMID: 33601148
- Total Syntheses and Chemical Biology Studies of Hymeglusin and Fusarilactone A, Novel Circumventors of β-Lactam Drug Resistance in Methicillin-Resistant Staphylococcus aureus. | Kanaida, M., et al. 2021. ChemMedChem. 16: 2106-2111. PMID: 33783142
- Hymeglusin Enhances the Pro-Apoptotic Effects of Venetoclax in Acute Myeloid Leukemia. | Zhou, C., et al. 2022. Front Oncol. 12: 864430. PMID: 35847946
- Human cytoplasmic 3-hydroxy-3-methylglutaryl coenzyme A synthase: expression, purification, and characterization of recombinant wild-type and Cys129 mutant enzymes. | Rokosz, LL., et al. 1994. Arch Biochem Biophys. 312: 1-13. PMID: 7913309
- Inhibition of 3-hydroxy-3-methylglutaryl-CoA synthase and cholesterol biosynthesis by beta-lactone inhibitors and binding of these inhibitors to the enzyme. | Greenspan, MD., et al. 1993. Biochem J. 289 (Pt 3): 889-95. PMID: 8094614
- Isopentenoid synthesis in eukaryotic cells. An initiating role for post-translational control of 3-hydroxy-3-methylglutaryl coenzyme A reductase. | Giron, MD., et al. 1993. Arch Biochem Biophys. 302: 265-71. PMID: 8097083
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Hymeglusin, 1 mg | sc-203077 | 1 mg | $292.00 | |||
Hymeglusin, 2.5 mg | sc-203077A | 2.5 mg | $546.00 |