1-(3'-溴苯基)乙基胺 | 74892-97-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 1-(3'-溴苯基)乙基胺
• 英文名称: cholesteryl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoate)
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
• CAS: 74892-97-0
• 化学式: C₄₇H₇₄O₂
• 分子量: 671.103
• InChiKey: XZFUGMCJZFRBKF-BDJFIEMMSA-N

物化性质

• 沸点：
  697.2±54.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿：10mg/mL
• 碰撞截面：
  293.9 Ų [M+H]+ [CCS Type: TIMS, Method: calibrated with 4 ions from ESI LC/MS tuning mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  14.9
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

制备方法与用途

生物活性的CE(20:5(5Z,8Z,11Z,14Z,17Z)) 是一种内源性代谢产物。

| Human Endogenous Metabolite |

反应信息

• 作为反应物：
  描述：

  1-(3'-溴苯基)乙基胺 、 盐酸 生成 二十碳五烯酸甲酯
  参考文献：
  名称：

  HOVING, EDDA B.;JANSEN, GEERT;VOLMER, MARCEL;VAN, DOORMAAL JASPER J.;MUSK+, J. CHROMATOGR. BIOMED. APPL., 434,(1988) N, C. 395-409

  摘要：

  DOI：
• 作为产物：
  描述：

  全顺式二十碳五烯酸 、 胆固醇 在 pseudomonas lipase 作用下， 以 水 为溶剂， 反应 24.0h， 以88%的产率得到1-(3'-溴苯基)乙基胺
  参考文献：
  名称：

  酶法合成多不饱和脂肪酸的甾醇酯

  摘要：

  AbstractSteryl esters of long‐chain fatty acids have water‐holding properties, and polyunsaturated fatty acids (PUFA) have various physiological functions. Because steryl ester of PUFA can be expected to have both features, we attempted to synthesize steryl esters of PUFA by enzymatic methods. Among lipases used, Pseudomonas lipase was the most effective for the synthesis of cholesteryl docosahexaenoate. When a mixture of cholesterol/docosahexaenoic acid (3:1, mol/mol), 30% water, and 3000 units/g of lipase was stirred at 40°C for 24 h, the esterification extent attained 89.5%. Under the same reaction conditions, cholesterol, cholestanol, and sitosterol were also esterified efficiently with docosahexaenoic, eicosapentaenoic, arachidonic, and γ‐linolenic acids.

  DOI：

  10.1007/s11746-999-0164-6

文献信息

• Negative Charge at Amino Acid 149 Is the Molecular Determinant for Substrate Specificity of Lecithin:Cholesterol Acyltransferase for Phosphatidylcholine Containing 20-Carbon <i>sn</i>-2 Fatty Acyl Chains
  作者：Yue Zhao、Jingchuan Wang、Abraham K. Gebre、Jeffrey W. Chisholm、John S. Parks

  DOI：10.1021/bi035460u

  日期：2003.12.1

  demonstrated higher activity with PC species containing 20-carbon, but not 18-carbon, sn-2 fatty acyl chains. The increased activity of hE149A was due to an increase in apparent V(max) but not to apparent K(m) or LCAT binding to the PC surface. Substitution of different amino acids in the 149 position of hLCAT showed that activation of the enzyme with sn-2 20:4 containing PC substrate was only observed when

  我们先前描述了人LCAT中的点突变（在残基149处为A； hE149A），与野生型酶[hLCAT; Wang等。（1997）J.Biol。化学 272，280-286]，得到具有与大鼠LCAT相似的底物特异性的人类酶。本研究的目的是探讨氨基酸149在确定脂肪酰基底物特异性中的作用的分子基础。在第一个实验中，大鼠LCAT（rA149E）的反向突变将大鼠LCAT的底物特异性转化为人类酶的底物特异性，证明了该突变是上下文无关的和可逆的。在第二个实验中 我们发现与hLCAT相比，hE149A对含有20个碳而不是18个碳的sn-2脂肪酰基链的PC物种具有更高的活性。hE149A活性的提高是由于表观V（max）的增加，而不是由于表观K（m）或LCAT与PC表面的结合。在hLCAT的149位上取代了不同的氨基酸，表明只有在去除残基149上的负电荷时，才用含sn-2 20：4的PC底物激活该酶。我们得出的
• Differential Modulation of ACAT1 and ACAT2 Transcription and Activity by Long Chain Free Fatty Acids in Cultured Cells
  作者：Toru Seo、Peter M. Oelkers、Mara R. Giattina、Tilla S. Worgall、Stephen L. Sturley、Richard J. Deckelbaum

  DOI：10.1021/bi0022947

  日期：2001.4.1

  Fatty acyl CoA and cholesterol are the substrates for cholesteryl ester synthesis by acyl coenzyme A:cholesterol acyltransferase (ACAT). Two ACAT genes have been identified ACAT1 is expressed ubiquitously while ACAT2 is primarily expressed in intestine and liver, We tested effects of different free fatty acids (FFAs) on ACAT1 and ACAT2 expression and activity in HepG2 human hepatocytes and THP1 human macrophages. Incubation of oleic acid, arachidonic acid, or eicosapentaenoic acid, but not 25-hydroxycholesterol, induced ACAT1 mRNA levels 1.5-2-fold in HepG2, with no affect on ACAT2 mRNA. FFA had no affect on ACAT1 mRNA in THP1 cells. To determine if FFAs affect ACAT1 or ACAT2 posttranscriptionally, cells were labeled with [H-3]cholesterol in the presence of the different FFAs for 1-5 h. Both HepG2 and THP1 cells showed the greatest cholesteryl ester production with oleic acrid. This was also confirmed by the observation that more [H-3]oleic acid incorporated into CE compared to [H-3]eicosapentaenoic acid, even though there was no difference in the total uptake of these FFAs. In ACAT-deficient SRD4, CHO cells stably transfected with human ACAT1 or ACAT2, ACAT1 expressing cells showed a strong preference for oleic acid while ACAT2 expressing cells utilized unsaturated FFAs. Acyl CoA substrate specificity was further tested in microsomes isolated from these cells as well as HepG2 and THP1, THP1 and ACAT1 cells utilized oleoyl CoA preferentially. In contrast, HepG2 and ACAT2 microsomes utilized linolenoyl CoA as well. We conclude that FFAs increase ACAT1 mRNA levels in a cell specific manner, and furthermore that the ACAT reactions exhibit differential FFA utilization.