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製品名
Hymeglusin, ≥98% (HPLC), from Fusarium sp.
由来生物
Fusarium sp.
品質水準
アッセイ
≥98% (HPLC)
フォーム
powder
溶解性
DMSO: soluble
H2O: insoluble
acetone: soluble
chloroform: soluble
ethyl acetate: soluble
保管温度
−20°C
SMILES記法
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
生物化学的／生理学的作用
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.
調製ノート
A DMSO solution (1 mg/mL) is stable for one month at −20 °C.
保管分類コード
11 - Combustible Solids
WGK
WGK 3
引火点(°F)
Not applicable
引火点(℃)
Not applicable
適用法令
試験研究用途を考慮した関連法令を主に挙げております。化学物質以外については、一部の情報のみ提供しています。 製品を安全かつ合法的に使用することは、使用者の義務です。最新情報により修正される場合があります。WEBの反映には時間を要することがあるため、適宜SDSをご参照ください。
Jan Code
SML0301-BULK:
SML0301-VAR:
SML0301-1MG:
SML0301-1MG-PW:
最新バージョンのいずれかを選択してください：
試験成績書（COA）
Lot/Batch Number
H Hashizume et al.
Chemical & pharmaceutical bulletin, 42(10), 2097-2107 (1994-10-01)
Structural analogs of 1233A, a microbial metabolite inhibiting 3-hydroxy-3- methylglutaryl coenzyme A (HMG-CoA) synthase, were designed and synthesized. The 2-oxetanone moiety was left intact. All analogs prepared were tested for inhibition of HMG-CoA synthase activity and sterol synthesis in mouse
Specific binding of beta-lactone 1233A to 3-hydroxy-3-methylglutaryl-coenzyme A synthase.
H Tomoda et al.
The Journal of antibiotics, 46(5), 872-874 (1993-05-01)
D Andrew Skaff et al.
Biochemistry, 51(23), 4713-4722 (2012-04-19)
Hymeglusin (1233A, F244, L-659-699) is established as a specific β-lactone inhibitor of eukaryotic hydroxymethylglutaryl-CoA synthase (HMGCS). Inhibition results from formation of a thioester adduct to the active site cysteine. In contrast, the effects of hymeglusin on bacterial HMG-CoA synthase, mvaS
T Sunazuka et al.
The Journal of antibiotics, 45(7), 1139-1147 (1992-07-01)
Simple and efficient syntheses of 1233A analogs were developed and the inhibitory activity of the analogs against hydroxymethylglutaryl coenzyme A (HMG-CoA) synthase was determined. Study of the structure-activity relationships revealed that not only the geometry in beta-lactone moiety but also
M D Greenspan et al.
Proceedings of the National Academy of Sciences of the United States of America, 84(21), 7488-7492 (1987-11-01)
A beta-lactone isolated from Fusarium sp. has been shown to be a potent specific inhibitor of the enzyme 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase [(S)-3-hydroxy-3-methylglutaryl-CoA acetoacetyl-CoA-lyase (CoA-acetylating), EC, 4.1.3.5] from rat liver. The structure of this beta-lactone, termed L-659,699, is (E,E)-11-[3-(hydroxy-methyl)-4-oxo-2-oxytanyl]-3,5,7-trimethyl-2,4
アクティブなフィルタ
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