Merck
所有图片(4)

A9384

Sigma-Aldrich

S-(5′-腺苷)-L-高半胱氨酸

crystalline

别名:
5′-脱氧-S-腺苷-L-高半胱氨酸, S-(5′-脱氧腺苷-5′)-L-高半胱氨酸, AdoHcy
Empirical Formula (Hill Notation):
C14H20N6O5S
CAS号:
分子量:
384.41
Beilstein:
99188
EC 号:
MDL编号:
eCl@ss:
32160406
PubChem化学物质编号:
NACRES:
NA.51

质量水平

300

形式

crystalline

溶解性

1 M HCl: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow

储存温度

−20°C

SMILES string

N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)C(O)=O

InChI

1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1

InChI key

ZJUKTBDSGOFHSH-WFMPWKQPSA-N

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应用

SAH适用于:
  • 研究AdoHcy是否与AdoMet竞争下调LUC报告基因的活性
  • 作为研究SAH丰度模式及其与脊椎动物变态的相关性的试剂
  • 用于优化蛋白质(赖氨酸K)甲基转移酶SET7/9活性测定
  • 在登革病毒甲基转移酶活性测定过程中用于荧光偏振(FP)分析
  • 作为通过高效液相色谱(HPLC)和荧光检测法测定血液样品SAH含量的标准品

包装

10, 25, 50, 100 mg in glass bottle

生化/生理作用

S-(5′-腺苷)-L-高半胱氨酸(AdoHcy/SAH)是细胞内高半胱氨酸应激的一个组成部分。AdoHcy是参与表观遗传学的DNA甲基转移酶(S-腺苷-L-甲硫氨酸(AdoMet)依赖的甲基转移酶)的竞争性抑制剂(与AdoMet竞争)。因此,AdoHcy可用于各种高同型半胱氨酸状态的表观遗传学研究。AdoHcy是被S-腺苷高半胱氨酸水解酶(AHCY)代谢的。AdoHcy是S-腺苷甲硫氨酸(SAM)相关的酶促转甲基反应的产物。通过其切割产生腺苷和L-高半胱氨酸,将其重新转化为SAM——它是噻亭高半胱氨酸S-甲基转移酶的底物。血浆中SAM和SAH的浓度变化可作为细胞甲基化潜能和代谢变化的预测因子。甲基化能力代表特定的遗传多态性和/或营养缺乏。甲基化在表观遗传学、重编程和癌症中具有重要作用。

储存分类代码

13 - Non Combustible Solids

WGK

WGK 3

闪点(F)

Not applicable

闪点(C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

分析证书

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原产地证书 (CofO)

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Desirée E C Smith et al.
Clinical chemistry and laboratory medicine, 50(9), 1641-1647 (2012-09-11)
Disturbances in the levels of one-carbon (1C) metabolism metabolites have been associated with a wide variety of neuropsychiatric diseases. Cerebrospinal fluid (CSF) levels of homocysteine (Hcy) and the other 1C metabolites, nor their interrelatedness and putative determinants, have been studied
S Melnyk et al.
Clinical chemistry, 46(2), 265-272 (2000-02-05)
The relative changes in plasma and intracellular concentrations of S-adenosylmethionine (SAM) and S-adenosylhomocysteine (SAH) may be important predictors of cellular methylation potential and metabolic alterations associated with specific genetic polymorphisms and/or nutritional deficiencies. Because these metabolites are present in nanomolar
E A Struys et al.
Clinical chemistry, 46(10), 1650-1656 (2000-10-06)
Available methods for the determination of nanomolar concentrations of S:-adenosylmethionine (SAM) and S:-adenosylhomocysteine (SAH) in plasma and cerebrospinal fluid (CSF) are time-consuming. We wished to develop a method for their rapid and simultaneous measurement. We used tandem mass spectrometry (MS/MS)
Siew Pheng Lim et al.
Methods in molecular biology (Clifton, N.J.), 1030, 249-268 (2013-07-04)
Flavivirus NS5 is the most conserved protein amongst the flavivirus proteins and is an essential enzyme for viral mRNA capping and replication. It encodes a methyl-transferase (MTase) domain at its N-terminal region which carries out sequential N7 and 2'-O methylation
S C Lu
The international journal of biochemistry & cell biology, 32(4), 391-395 (2000-04-13)
S-Adenosyl-Lmethionine (SAM) is an important molecule in normal cell function and survival. SAM is utilized by three key metabolic pathways: transmethylation; transsulfuration; and polyamine synthesis. In transmethylation reactions, the methyl group of SAM is donated to a large variety of

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