乙醇胺-15N | 33598-78-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 乙醇胺-15N
• 中文别名: 乙醇胺-¹⁵N
• 英文名称: [¹⁵N]-ethanolamine
• 英文别名: 15N-ethanolamine；ethanolamine-15N；2-[¹⁵N]amino-ethanol；(15)N-ethanolamine；<¹⁵N>-2-Amino-aethanol；¹⁵N-Ethanolamin；2-(15N)azanylethanol
• CAS: 33598-78-6
• 化学式: C₂H₇NO
• 分子量: 62.077
• InChiKey: HZAXFHJVJLSVMW-LBPDFUHNSA-N

物化性质

• 熔点：
  11 °C(lit.)
• 沸点：
  170 °C(lit.)
• 密度：
  1.028 g/mL at 25 °C
• 闪点：
  93°C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  4
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙醇胺-15N 在 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以57%的产率得到2-chloroethylamine-(15)N hydrochloride
  参考文献：
  名称：

  Synthesis of 15N labelled isophosphoramide mustard

  摘要：

  合成了伊福酰胺代谢物异磷酰胺芥子气（IPM），并在每个氮位点进行了同位素富集。甘氨酸-15N 转化为 2-氯乙胺-15N 盐酸盐（4 个步骤，净产率 21%），然后与二氯磷酸苯酯反应，得到 N,N′-双（2-氯乙基）磷二酰胺-15N2 酸苯酯[62%，PhOP(O) (15NHCH2CH2Cl)2]。对这种苯基酯进行催化氢化，然后加入环己胺 (CHA)，得到了作为 CHA 盐的 IPM-15N2（63%）。

  DOI：

  10.1002/jlcr.2580340305
• 作为产物：
  描述：

  甘氨酸-15N 在 lithium aluminium tetrahydride 作用下， 生成 乙醇胺-15N
  参考文献：
  名称：

  Improved CILAT reagents for quantitative proteomics

  摘要：

  Improved CILAT reagents have been developed, with which an unprecedented number of protein samples can be measured in high-throughput assays, providing a robust tool for MS-based quantitative proteomics. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.022

文献信息

• Hydrolysis of Phosphotriesters:  Determination of Transition States in Parallel Reactions by Heavy-Atom Isotope Effects
  作者：Mark A. Anderson、Hyunbo Shim、Frank M. Raushel、W. W. Cleland

  DOI：10.1021/ja011025g

  日期：2001.9.1

  measured by isotope ratio mass spectrometry. Parallel reaction and incomplete labeling corrections were made for both systems. DEPC has a primary (18)O isotope effect of 1.041 +/- 0.003 and a secondary (18)O isotope effect of 1.033 +/- 0.002. The primary (18)O isotope effect for DEmNBP was 1.052 +/- 0.003. These large effects suggest a highly associative transition state in which the nucleophile approaches

  使用远程标记法测量了 O,O-二乙基磷酰胆碱碘 (DEPC) 碱性水解中的初级和次级 (18)O 同位素效应和 O,O-二乙基-二乙基磷酰胆碱 (DEPC) 碱性水解中的初级 (18)O 同位素效应。磷酸间硝基苄酯 (DEmNBP)。由于 pK 值的相似性，感兴趣的离去基团（胆碱或间硝基苯甲醇）和乙醇都可以在水解过程中排出。通过同位素比质谱法测量重原子同位素效应。对两个系统进行了平行反应和不完全标记校正。DEPC 的主要 (18)O 同位素效应为 1.041 +/- 0.003，次要 (18)O 同位素效应为 1.033 +/- 0.002。DEmNBP 的主要 (18)O 同位素效应为 1.052 +/- 0.003。这些巨大的影响表明存在高度缔合过渡态，其中亲核试剂非常接近磷原子以弹出离去基团。较大的值还表示反应坐标上的较大压缩或一般运动。
• Synthesis of15N and13C selectively labeled anandamide
  作者：Xiang-Qun Xie、Hongqin Yang、Greg Choi、Sunyuan Lin、Alexandros Makriyannis

  DOI：10.1002/jlcr.601

  日期：2002.8

  interest for pharmaceutical research and biochemistry in general. Here we report a novel synthetic pathway, which selectively introduces 15N and 13C isotopes into the anandamide molecule. This isotopically labeled AEA can be studied conformationally in its native binding condition via solid state NMR. These synthetic procedures can also be adapted to produce radioactive ligands for receptor binding assays

  Anandamide（图 1a）（花生四烯基乙醇酰胺，AEA），（5Z,8Z,11Z,14Z）-N-（2-羟乙基）-5,8,11,14-二十碳四烯酰胺，是一种具有重要生物活性的内源性大麻素配体。AEA 在其天然受体结合环境中的构象通常对药物研究和生物化学特别感兴趣。在这里，我们报告了一种新的合成途径，它选择性地将 15N 和 13C 同位素引入 anandamide 分子。这种同位素标记的 AEA 可以通过固态 NMR 在其天然结合条件下进行构象研究。这些合成程序也可用于生产用于受体结合分析和其他结构研究的放射性配体。版权所有 © 2002 John Wiley & Sons, Ltd.
• [EN] COMPOUND, DIAGNOSTIC AGENT, NUCLEAR MAGNETIC RESONANCE ANALYSIS METHOD, NUCLEAR MAGNETIC RESONANCE IMAGING METHOD, MASS SPECTROMETRY METHOD AND MASS SPECTROMETRY IMAGING METHOD<br/>[FR] COMPOSÉS, AGENT DE DIAGNOSTIC, PROCÉDÉ D'ANALYSE PAR RÉSONANCE MAGNÉTIQUE NUCLÉAIRE, PROCÉDÉ D'IMAGERIE PAR RÉSONANCE MAGNÉTIQUE NUCLÉAIRE, PROCÉDÉ DE SPECTROMÉTRIE DE MASSE ET PROCÉDÉ D'IMAGERIE PAR SPECTROMÉTRIE DE MASSE
  申请人：UNIV KYOTO

  公开号：WO2009031712A1

  公开（公告）日：2009-03-12

  To produce a labeled compound for a selected biological substance not using a radioisotope atom which has a risk of exposure to radioactivity and limitation on handling time but using a stable isotope atom; and that the labeled compound can be measured with good sensitivity separably from naturally occurring compounds of the selected biological substance which are substituted with the stable isotope atom. Choline as a biological substance is labeled by substituting the nitrogen atom of the quaternary ammonium group and all the carbon atoms of the methyl group attached to the nitrogen atom with respective isotopes 15N and 13C and used as a diagnostic agent.

  生物物质的标记化合物可以使用稳定同位素原子而不使用有辐射危险和处理时间限制的放射性同位素原子来生产，并且该标记化合物可以与所选生物物质的天然存在化合物分离地测量，这些化合物已经用稳定同位素原子替代。作为一种生物物质，胆碱通过用各自同位素15N和13C替换季铵基的氮原子和附着在氮原子上的甲基基团的所有碳原子来标记，并用作诊断试剂。
• Magnetic Resonance Imaging of Tumor with a Self-Traceable Phosphorylcholine Polymer
  作者：Hisatsugu Yamada、Yoshinori Hasegawa、Hirohiko Imai、Yuki Takayama、Fuminori Sugihara、Tetsuya Matsuda、Hidehito Tochio、Masahiro Shirakawa、Shinsuke Sando、Yu Kimura、Akio Toshimitsu、Yasuhiro Aoyama、Teruyuki Kondo

  DOI：10.1021/ja510479v

  日期：2015.1.21

  Polymers are concentration-amplified with respect to the monomeric units. We show here that a phosphorylcholine polymer enriched with C-13/N-15 at the methyl groups is self-traceable by multiple-resonance (heteronuclear-correlation) NMR in tumor-bearing mice inoculated with the mouse rectal cancer cell line (colon 26). Preliminary measurements indicated that the present polymeric nanoprobe was satisfactorily distinguished from lipids and detectable with far sub-micromolar spectroscopic and far sub-millimolar imaging sensitivities. Detailed ex vivo and in vivo studies for the tumor-bearing mice administered the probe with a mean molecular weight of 63 000 and a mean size of 13 nm, revealed the following: (1) this probe accumulates in the tumor highly selectively (besides renal excretion) and efficiently (up to 30% of the injected dose), (2) the tumor can thus be clearly in vivo imaged, the lowest clearly imageable dose of the probe being 100 mg/kg or 2.0 mg/20-g mouse, and (3) the competition between renal excretion and tumor accumulation is size-controlled; that is, the larger (higher molecular-weight) and smaller (lower molecular-weight) portions of the probe undergo tumor accumulation and renal excretion, respectively. The observed size dependence suggests that the efficient tumor-targeting of the present probe is stimulated primarily by the so-called enhanced permeability and retention (EPR) effect, that is, size-allowed invasion of the probe into the tumor tissue via defective vascular wall. Self-traceable polymers thus open an important area of magnetic resonance imaging (MRI) of tumors and may provide a highly potential tool to visualize various delivery/localization processes using synthetic polymers.
• Akoka, S.; Meir, C.; Tellier, C., Synthetic Communications, 1985, vol. 15, # 2, p. 101 - 108
  作者：Akoka, S.、Meir, C.、Tellier, C.、Belaud, C.、Poignant, S.

  DOI：——

  日期：——