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Merck

SML3737

Octyl-(S)-2HG

≥98% (HPLC), α-KG-dependent prolylhydroxylase antagonist, powder

別名:

(2S)-2-Hydroxyglutarate octyl ester, (2S)-Octyl-α-hydroxyglutarate, (S)-4-Hydroxy-5-(octyloxy)-5-oxopentanoic acid, 1-Octyl-L-2-hydroxyglutarate, 2S-Hydroxy-pentanedioic acid, 1-octyl ester, L-Octyl-2HG, L2HG, Octyl-(S)-2-hydroxyglutarate, Octyl-L-2HG, S-2HG octyl ester

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この商品について

実験式(ヒル表記法):
C13H24O5
CAS番号:
分子量:
260.33
UNSPSC Code:
12352200
NACRES:
NA.21
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
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製品名

Octyl-(S)-2HG, ≥98% (HPLC)

SMILES string

O[C@@H](CCC(=O)O)C(=O)OCCCCCCCC

InChI

1S/C13H24O5/c1-2-3-4-5-6-7-10-18-13(17)11(14)8-9-12(15)16/h11,14H,2-10H2,1H3,(H,15,16)/t11-/m0/s1

InChI key

UJZOKTKSGUOCCM-NSHDSACASA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Quality Level

Biochem/physiol Actions

Membrane-permeant precursor form of the oncometabolite L-2-hydroxyglutarate that inhibits α-ketoglutarate/α-KG-dependent dioxygenases.
Octyl-(S)-2HG (Octyl-L-2HG) is a membrane-permeant precursor form of the oncometabolite L-2-hydroxyglutarate (L2HG) produced from α‐KG by malate dehydrogenases (MDH1/2) and lactate dehydrogenase (LDHA). L2HG can be converted back to α-KG by L-2-hydroxyglutarate dehydrogenase (LHGDH), deletion or mutations of which lead to L2HG accumulation, metabolic disorders and reduced 5hmC levels. Both D- and L-2HG inhibit Jumonji histone demethylases and Tet oxygenases by competing against α-KG binding. However, L2HG is an antagonist, while R2HG (D2HG) is an agonist of α-KG-dependent prolylhydroxylase (EglN).

保管分類

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

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。

SML3737-10MG: + SML3737-BULK: + SML3737-VAR: + SML3737-50MG:

jan


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D J Wilson et al.
American journal of ophthalmology, 103(2), 167-179 (1987-02-15)
We studied 49 eyes obtained post mortem from 43 patients who had previously had retinal detachment surgery to evaluate some of the factors known to complicate retinal detachment. The retina had been successfully reattached in 44 of 49 eyes. We
Hanna Tarhonskaya et al.
Journal of molecular biology, 429(19), 2895-2906 (2017-08-23)
Methylation of lysine-4 of histone H3 (H3K4men) is an important regulatory factor in eukaryotic transcription. Removal of the transcriptionally activating H3K4 methylation is catalyzed by histone demethylases, including the Jumonji C (JmjC) KDM5 subfamily. The JmjC KDMs are Fe(II) and
Wanshu Ma et al.
Science advances, 7(18) (2021-05-02)
Recent findings indicate that mitochondrial respiration regulates blood endothelial cell proliferation; however, its role in differentiating lymphatic endothelial cells (LECs) is unknown. We hypothesized that mitochondria could work as a sensor of LECs' metabolic specific needs by determining their functional
Xudong Fu et al.
Cell metabolism, 22(3), 508-515 (2015-07-21)
We discovered recently that the central metabolite α-ketoglutarate (α-KG) extends the lifespan of C. elegans through inhibition of ATP synthase and TOR signaling. Here we find, unexpectedly, that (R)-2-hydroxyglutarate ((R)-2HG), an oncometabolite that interferes with various α-KG-mediated processes, similarly extends
Vineet K Gupta et al.
Cancer research, 81(15), 4001-4013 (2021-05-16)
In pancreatic cancer, the robust fibroinflammatory stroma contributes to immune suppression and renders tumors hypoxic, altering intratumoral metabolic pathways and leading to poor survival. One metabolic enzyme activated during hypoxia is lactate dehydrogenase A (LDHA). As a result of its

ライフサイエンス、有機合成、材料科学、クロマトグラフィー、分析など、あらゆる分野の研究に経験のあるメンバーがおります。.

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