(R,R)-Hymeglusin

• CAT Number: I007557
• CAS Number: 29066-42-0
• Molecular Formula: C₁₈H₂₈O₅
• Molecular Weight: 324.41
• Purity: ≥95%
• Solubility: Soluble in DMSO
• Storage: -20°C
• IUPAC Name: (2E,4E,7R)-11-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetan-2-yl]-3,5,7-trimethylundeca-2,4-dienoic acid
• InChI: InChI=1S/C18H28O5/c1-12(8-13(2)9-14(3)10-17(20)21)6-4-5-7-16-15(11-19)18(22)23-16/h9-10,12,15-16,19H,4-8,11H2,1-3H3,(H,20,21)/b13-9+,14-10+/t12-,15-,16-/m1/s1
• InChIKey: ODCZJZWSXPVLAW-KXCGKLMDSA-N
• SMILES: CC(CCCCC1C(C(=O)O1)CO)CC(=CC(=CC(=O)O)C)C

L-659,699, also known as hymeglusin (CAT: I007557), is a fungal β-lactone antibiotic with pharmacological action as an inhibitor of HMG-CoA synthase. It exerts its inhibitory effect by covalently modifying the active Cys129 residue of the enzyme. HMG-CoA synthase is a key enzyme involved in the biosynthesis of cholesterol and other important molecules in the mevalonate pathway. By inhibiting HMG-CoA synthase, L-659,699 disrupts the synthesis of mevalonate and downstream metabolites. This compound has been studied for its potential therapeutic applications in conditions such as hypercholesterolemia and other metabolic disorders.

Reference

1:The reversal of the inhibition on lipids synthesis by L-659,699 in arterial smooth muscle cells cultures. Carazo A, Alejandre MJ, Louktibi A, Linares A.Mol Cell Biochem. 2001 May;221(1-2):25-31. PMID: 11506182
2:Inhibition of hydroxymethylglutaryl-coenzyme A synthase by L-659,699. Greenspan MD, Yudkovitz JB, Lo CY, Chen JS, Alberts AW, Hunt VM, Chang MN, Yang SS, Thompson KL, Chiang YC, et al.Proc Natl Acad Sci U S A. 1987 Nov;84(21):7488-92. PMID: 2890166 Free PMC Article