Sodium 9-{5-O-[{[{4-[(2-{[2-(acetylsulfanyl)ethyl]carboximidato}ethyl)imino]-3,4-dihydroxy-2,2-dimethylbutoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-3-O-phosphonopentofuranosyl}-9H-purin-6-amine | 102029-73-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Sodium 9-{5-O-[{[{4-[(2-{[2-(acetylsulfanyl)ethyl]carboximidato}ethyl)imino]-3,4-dihydroxy-2,2-dimethylbutoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]-3-O-phosphonopentofuranosyl}-9H-purin-6-amine
• 英文别名: sodium;N-(2-acetylsulfanylethyl)-3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanimidate
• CAS: 102029-73-2
• 化学式: C23H37N7NaO17P3S
• 分子量: 831.6
• InChiKey: HNLIOWFIXSPFEC-WLYMNMRISA-M

物化性质

• 溶解度：
  H2O:100 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -4.94
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  392
• 氢给体数：
  8
• 氢受体数：
  22

安全信息

• 危险类别码：
  R23/24/25
• WGK Germany：
  1,3
• 海关编码：
  29349990
• 安全说明：
  S24,S36/37,S45

制备方法与用途

应用及发展前景

乙酸乙酯是清香型白酒的主体香，一直备受关注。通过基因工程手段提高酿酒酵母分泌乙酰辅酶A的能力，从而提高乙酸乙酯生成量。通过ACH1基因缺失的α5ΔACH1菌株表达发现，乙酰辅酶A含量较亲本菌株α5稍有提高，但对提高乙酸乙酯生成量的效果并不明显，分析原因可能是ACH1基因定位于线粒体中，其增加的是线粒体中乙酰辅酶A的含量，线粒体中的乙酰辅酶A无法流向乙酸乙酯的合成。在ACH1基因缺失的基础上，过表达ACS1和ACS2基因得到工程菌株α5-A1和α5-A2，乙酸乙酯生成量分别比亲本菌株α5提高26.12%和23.70%；乙酰辅酶A含量分别比α5ΔACH1提高了80.33%和52.79%；结果表明，过表达ACS1和ACS2基因均能提高乙酰辅酶A含量和乙酸乙酯生成量，且乙酸乙酯生成量和胞内乙酰辅酶A的增加量呈正相关。在过表达ACS1和ACS2基因的基础上，过表达醇乙酰基转移酶ATF1基因得到工程菌株A1-ATF1和
A2-ATF1，乙酸乙酯含量分别为72.52 mg/L和44.80 mg/L，分别是单独过表达ATF1基因a5-ATF1的204.14%和125.67%，且ΔA-ATF1比α5-ATF1产乙酸乙酯显著增加，结果表明，在底物乙酰辅酶A充足的条件下，提高醇乙酰基转移酶活性，能够提高乙酸乙酯的生成量。  

生物活性

Acetyl Coenzyme A trisodium (Acetyl-CoA trisodium) 是一种重要的代谢中间产物。Acetyl Coenzyme A trisodium 是糖酵解丙酮酸进入三羧酸 (TCA) 循环的实际分子，是脂质合成的关键前体，并且是乙酰基乙酰化的唯一供体，还是一种丙酮酸羧化酶 (PC) 的有效变构活化剂。

体外研究

Acetyl-coenzyme A (Acetyl-CoA) is a membrane-impermeant molecule constituted by an acetyl moiety (CH3CO) linked to coenzyme A (CoA), a derivative of vitamin B5 and cysteine, through a thioester bond. As thioester bonds are energy rich, the chemical structure of acetyl-CoA facilitates the transfer of the acetyl moiety to a variety of acceptor molecules, including amino groups on proteins.
In most mammalian cells, Acetyl-coenzyme A (Acetyl-CoA) is predominantly generated in the mitochondrial matrix by various metabolic circuitries, namely glycolysis, β-oxidation, and the catabolism of branched amino acids. Cytosolic Acetyl-coenzyme A is the precursor of multiple anabolic reactions that underlie the synthesis of fatty acids and steroids, as well as specific amino acids including glutamate, proline, and arginine.

体内研究

Mice deprived of food (but with access to water ad libitum) for 24 hr exhibit a significant reduction in total Acetyl-coenzyme A (Acetyl-CoA) levels in several organs, including the heart and muscles, corresponding to a decrease in protein acetylation levels. However, the same experimental conditions have no major effects on Acetyl-coenzyme A concentrations in the brain and actually increase hepatic Acetyl-coenzyme A and protein acetylation levels. Ethanol intake augments Acetyl-coenzyme A levels in hepatic mitochondria.