3-amino-N-(2,2,6,6-tetramethyl-1-oxy-4-piperidinyl)propionamide | 174755-33-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-amino-N-(2,2,6,6-tetramethyl-1-oxy-4-piperidinyl)propionamide
• CAS: 174755-33-0
• 化学式: C₁₂H₂₄N₃O₂
• 分子量: 242.341
• InChiKey: YZCZRLLMHJQQGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  59.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡啶-2-甲醛 、 3-amino-N-(2,2,6,6-tetramethyl-1-oxy-4-piperidinyl)propionamide 以 乙醇 为溶剂， 反应 2.0h， 生成 2-<((2-(((2,2,6,6-tetramethyl-1-oxy-4-piperidinyl)amino)carbonyl)ethyl)imino)methyl>pyridine
  参考文献：
  名称：

  金属-硝酰基相互作用。39. 硝酰基自旋标记的锰 (II) 配合物在流体溶液中的 EPR 光谱中的电子-电子自旋-自旋分裂

  摘要：

  Les specters RPE en bande X et Q sont obtenus pour une serie de coordinats a spin marque lies aux bis-(hexafluoroacetylacetonato) Mn(II) et tris-(trifluoroacetylacetonato) Mn(II) en溶液。Obtention et analysis des constantes de couplage d'echange J

  DOI：

  10.1021/ja00331a002
• 作为产物：
  描述：

  Boc-β-Ala-TEMPO 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-amino-N-(2,2,6,6-tetramethyl-1-oxy-4-piperidinyl)propionamide
  参考文献：
  名称：

  Structural Factors Controlling the Spin–Spin Exchange Coupling: EPR Spectroscopic Studies of Highly Asymmetric Trityl–Nitroxide Biradicals

  摘要：

  Highly asymmetric exchange-coupled biradicals, e.g., the trityl-nitroxides (TNs), possess particular magnetic properties that have opened new possibilities for their application in biophysical, physicochemical, and biological studies. In the present work, we investigated the effect of the linker length on the spin-spin coupling interaction (J) in TN biradicals using the newly synthesized biradicals CT02-GT, CT02-AT, CT02-VT, and CT02-PPT as well as the previously reported biradicals TNN14 and TN1. The results show that the magnitude of J can be easily tuned from similar to 4 G (conformer 1 in CT02-PPT) to >1200 G (in TNN14) by varying the linker separating the two radical moieties and changing the temperature. Computer simulations of EPR spectra were carried out to estimate J values of the TN biradicals directly. In addition to the spin-spin coupling interaction of TN biradicals, their g, hyperfine-splitting, and zero-field-splitting interactions were explored at low temperature (220 K). Our present study clearly shows that varying the spin-spin interaction as a function of linker distance and temperature provides an effective strategy for the development of new TN biradicals that can find wide applications in relevant fields.

  DOI：

  10.1021/ja311571v

文献信息

• Syntheses and Transglutaminase-Catalyzed Incorporation of Novel Spin-Labeled Primary Amines into Proteins
  作者：Chakravarthy Narasimhan、Ching-San Lai、Joy Joseph

  DOI：10.1006/bioo.1996.0006

  日期：1996.3

  A series of spin-labeled primary amine derivatives, namely, 2,2,6,6-tetramethyl-piperidinyl-1-oxyl-4-amidoalkylamines with varying alkyl chain lengths, have been synthesized. The spin-labeled primary amine with a tetramethylene or a pentamethylene chain covalently modifies human plasma fibronectin with a stoichiometry of 0.97-to-1.0 (probe-to-subunit) in the presence of coagulation factor XIIIa. The labels with two or one methylene chain also similarly modify fibronectin, but with a stoichiometry of only about 0.3-0.4 per subunit. The spin-labeled primary amine with a trimethylene chain does not label fibronectin. The labeling site appears to be the glutamine-3 residue at the amino-terminal region of fibronectin. Electron spin resonance studies show that the bound labels are partially immobilized with an effective rotational correlation time of 0.4-0.6 ns. The spin-labeled primary amine with tetramethylene chain also is shown to covalently incorporate into bee venom melittin in the presence of guinea-pig liver transglutaminase. The syntheses of the various spin-labeled primary amines and their applications in the study of structure and dynamics of different proteins and peptides are discussed. The observations from this study suggest that these spin-labeled primary amines have potentially wide application as structural probes. (C) 1996 Academic Press, Inc.