SML0301
Hymeglusin
from Fusarium sp., ≥98% (HPLC), powder, HMG-CoA synthase inhibitor
别名:
(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
产品名称
Hymeglusin, ≥98% (HPLC), from Fusarium sp.
生物来源
Fusarium sp.
质量水平
方案
≥98% (HPLC)
表单
powder
溶解性
DMSO: soluble
H2O: insoluble
acetone: soluble
chloroform: soluble
ethyl acetate: soluble
储存温度
−20°C
SMILES字符串
O1[C@@H]([C@H](C1=O)CO)CCCC[C@H](C\C(=C\C(=C\C(=O)O)\C)\C)C
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
生化/生理作用
Hymeglusin is a specific β lactone inhibitor of eukaryotic hydroxymethylglutaryl-CoA synthase (HMGCS), a key enzyme in the cholesterol biosynthetic pathway.
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.
制备说明
A DMSO solution (1 mg/mL) is stable for one month at −20 °C.
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
法规信息
新产品
此项目有
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
H Kumagai et al.
The Journal of antibiotics, 43(4), 397-402 (1990-04-01)
A new screening method for specific inhibitors of mevalonate biosynthesis was established using Vero cells, an animal cell line. The cultures selected were those which inhibited the growth of Vero cells in the EAGLE's minimum essential medium supplemented with 2%
Potent inhibitory effect of antibiotic 1233A on cholesterol biosynthesis which specifically blocks 3-hydroxy-3-methylglutaryl coenzyme A synthase.
S Omura et al.
The Journal of antibiotics, 40(9), 1356-1357 (1987-09-01)
N Aboushadi et al.
Biochemistry, 39(1), 237-247 (2000-01-08)
We have previously identified a CHO cell line (UT2 cells) that expresses only one 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase protein which is localized exclusively in peroxisomes [Engfelt, H.W., Shackelford, J.E., Aboushadi, N., Jessani, N., Masuda, K., Paton, V.G., Keller, G.A.
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.
The Journal of antibiotics, 41(2), 247-249 (1988-02-01)
M L Ginger et al.
The Journal of biological chemistry, 276(15), 11674-11682 (2001-01-20)
The amino acid leucine is efficiently used by the trypanosomatid Leishmania mexicana for sterol biosynthesis. The incubation of [2-(13)C]leucine with L. mexicana promastigotes in the presence of ketoconazole gave 14alpha-methylergosta-8,24(24(1))-3beta-ol as the major sterol, which was shown by mass spectrometry
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