Hymeglusin

SIGMA/SML0301 - ≥98% (HPLC), from Fusarium sp.

Synonym: (2E, 4E, 7R)-11-[(2R,3R)-3-(Hydroxymethyl)-4-oxooxetan-2-yl]-3,5,7-trimethylundeca-2,4-dienoic acid; Antibiotic 1233A; F-244; L-659,699

CAS Number: 29066-42-0
Empirical Formula (Hill Notation): C₁₈H₂₈O₅
Molecular Weight: 324.41
Linear Formula: C₁₈H₂₈O₅
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-SML0301-1MG	1 mg	$388.00 1/EA	Add To Favorites

This image is provided for informative purposes only and does not represent an actual product label. It should not be used as a substitute for official product labeling.

Properties
Descriptions
Safety Info.
Basic Data

assay	≥98% (HPLC)
biological source	Fusarium sp.
form	powder
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
InChI key	ODCZJZWSXPVLAW-KXCGKLMDSA-N
Quality Level	200
SMILES string	O1[C@@H]([C@H](C1=O)CO)CCCC[C@H](CC(=CC(=CC(=O)O)C)C)C
solubility	acetone: soluble
	chloroform: soluble
	DMSO: soluble
	ethyl acetate: soluble
	H₂O: insoluble
storage temp.	−20°C

Biochem/physiol Actions:	Hymeglusin is a specific β lactone inhibitor of eukaryotic hydroxymethylglutaryl-CoA synthase (HMGCS), a key enzyme in the cholesterol biosynthetic pathway.
Biochem/physiol Actions:	Hymeglusin is a specific β lactone inhibitor of eukaryotic hydroxymethylglutaryl-CoA synthase (HMGCS), a key enzyme in the cholesterol biosynthetic pathway. Unlike other fungal metabolites, Hymeglusin inhibits mevalonate biosynthesis by acting on HMG-CoA synthase, while other fungal metabolites such as Lovastatin (Mevinolin) and Compactin act as specific competitive inhibitors of the HMG-CoA reductase. Inhibition results from covalent modification of the active Cys¹²⁹ residue by the enzyme by the formation of a thioester adduct in the active site. Hymeglusin show no inhibitory effect against fatty acid synthetase purified from Sacharomyces serevisiae. Hymeglusin was found to block the growth of Enterococcus faecalis. After removal of the inhibitor from the culture medium, a growth curve inflection point is observed. Upon Hymeglusin inactivation, enzyme activity is restored at a rate that is 8-fold faster for human HMGCS than for the bacterial enzyme (mvaS). Structural studies explain these differences. Hymeglusin was also found to inhibit the replication of the dengue live virus (DEN-2 NGC virus) in K562 cells. Lovastatin inhibits DEN-2 NGC live virus replication in human peripheral blood mononuclear cells.
Preparation Note:	A DMSO solution (1 mg/mL) is stable for one month at −20 °C.

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥98% (HPLC)
Storage Temp.	−20°C
UNSPSC	51111800

To Order From a Quote