A9384
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, AdoHcy, S-(5′-脱氧腺苷-5′)-L-高半胱氨酸
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关于此项目
经验公式（希尔记法）:
C14H20N6O5S
化学文摘社编号:
分子量:
384.41
NACRES:
NA.51
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
41106305
EC Number:
213-560-8
MDL number:
Beilstein/REAXYS Number:
99188
产品名称
S-(5′-腺苷)-L-高半胱氨酸, crystalline
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
SMILES string
N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23)C(O)=O
assay
≥98.0% (HPLC)
≥98.0% (TLC)
form
crystalline
mol wt
384.41
solubility
1 M HCl: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow
storage temp.
−20°C
Quality Level
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Application
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
Biochem/physiol Actions
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。
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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
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)
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
Wenyu Yu et al.
Bioorganic & medicinal chemistry, 21(7), 1787-1794 (2013-02-26)
Chemical inhibition of proteins involved in chromatin-mediated signaling is an emerging strategy to control chromatin compaction with the aim to reprogram expression networks to alter disease states. Protein methyltransferases constitute one of the protein families that participate in epigenetic control
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