3-(金刚烷-1-基氨基)-3-氧代丙酸 | 156210-17-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(金刚烷-1-基氨基)-3-氧代丙酸
• 英文名称: (N-adamantylcarbamoyl)acetic acid
• 英文别名: 3-(1-Adamantylamino)-3-oxopropanoic acid
• CAS: 156210-17-2
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: OMPYJFAYYUEIPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  476.4±24.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(金刚烷-1-基氨基)-3-氧代丙酸 在 碘 、 2-肟氰乙酸乙酯 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N1,N1'-(disulfanediylbis(ethane-2,1-diyl))bis(N3-((3s,5s,7s)-adamantan-1-yl)malonamide)
  参考文献：
  名称：

  Modulation of Amyloidogenic Protein Self-Assembly Using Tethered Small Molecules

  摘要：

  Protein-protein interactions (PPIs) are involved in many of life's essential biological functions yet are also an underlying cause of several human diseases, including amyloidosis. The modulation of PPIs presents opportunities to gain mechanistic insights into amyloid assembly, particularly through the use of methods which can trap specific intermediates for detailed study. Such information can also provide a starting point for drug discovery. Here, we demonstrate that covalently tethered small molecule fragments can be used to stabilize specific oligomers during amyloid fibril formation, facilitating the structural characterization of these assembly intermediates. We exemplify the power of covalent tethering using the naturally occurring truncated variant (ΔN6) of the human protein β2-microglobulin (β2m), which assembles into amyloid fibrils associated with dialysis-related amyloidosis. Using this approach, we have trapped tetramers formed by ΔN6 under conditions which would normally lead to fibril formation and found that the degree of tetramer stabilization depends on the site of the covalent tether and the nature of the protein-fragment interaction. The covalent protein-ligand linkage enabled structural characterization of these trapped, off-pathway oligomers using X-ray crystallography and NMR, providing insight into why tetramer stabilization inhibits amyloid assembly. Our findings highlight the power of "post-translational chemical modification" as a tool to study biological molecular mechanisms.

  DOI：

  10.1021/jacs.0c10629
• 作为产物：
  描述：

  N-Adamantan-1-yl-malonamic acid methyl ester 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 生成 3-(金刚烷-1-基氨基)-3-氧代丙酸
  参考文献：
  名称：

  Design and Synthesis of Calcium and Magnesium Ionophores Based on Double-Armed Diazacrown Ether Compounds and Their Application to an Ion Sensing Component for an Ion-Selective Electrode

  摘要：

  The double-armed diazacrown ethers, which have a base diazacrown ether ring with two diamide-type side chains, were designed and synthesized on the basis of the proposed molecular model for the novel neutral Ca2+ and Mg2+ ionophores. The potentiometric ion-selective electrodes were prepared with over 20 kinds of systematically synthesized diazacrown ether derivatives. The relationship between the molecular structures of the ionophores and the ion selectivities was fully discussed. The electrodes based on the 21- and 18-membered diazacrown ether derivatives possessing a glycolic diamide and malonic diamide in their side chains (K23E1 and K22B5) exhibited excellent Ca2+ and Mg2+ selectivities, respectively. The ion-selectivity features of the novel Ca2+ and Mg2+ ionophores supply important structural information about the design of host molecules for alkaline earth metal cations.

  DOI：

  10.1021/ac00098a016

文献信息

• CN115724780
  申请人：——

  公开号：——

  公开（公告）日：——
• Modulation of Amyloidogenic Protein Self-Assembly Using Tethered Small Molecules
  作者：Emma E. Cawood、Nicolas Guthertz、Jessica S. Ebo、Theodoros K. Karamanos、Sheena E. Radford、Andrew J. Wilson

  DOI：10.1021/jacs.0c10629

  日期：2020.12.9

  Protein-protein interactions (PPIs) are involved in many of life's essential biological functions yet are also an underlying cause of several human diseases, including amyloidosis. The modulation of PPIs presents opportunities to gain mechanistic insights into amyloid assembly, particularly through the use of methods which can trap specific intermediates for detailed study. Such information can also provide a starting point for drug discovery. Here, we demonstrate that covalently tethered small molecule fragments can be used to stabilize specific oligomers during amyloid fibril formation, facilitating the structural characterization of these assembly intermediates. We exemplify the power of covalent tethering using the naturally occurring truncated variant (ΔN6) of the human protein β2-microglobulin (β2m), which assembles into amyloid fibrils associated with dialysis-related amyloidosis. Using this approach, we have trapped tetramers formed by ΔN6 under conditions which would normally lead to fibril formation and found that the degree of tetramer stabilization depends on the site of the covalent tether and the nature of the protein-fragment interaction. The covalent protein-ligand linkage enabled structural characterization of these trapped, off-pathway oligomers using X-ray crystallography and NMR, providing insight into why tetramer stabilization inhibits amyloid assembly. Our findings highlight the power of "post-translational chemical modification" as a tool to study biological molecular mechanisms.
• Design and Synthesis of Calcium and Magnesium Ionophores Based on Double-Armed Diazacrown Ether Compounds and Their Application to an Ion Sensing Component for an Ion-Selective Electrode
  作者：Koji. Suzuki、Kazuhiko. Watanabe、Yukihiro. Matsumoto、Mitsuru. Kobayashi、Sayaka. Sato、Dwi. Siswanta、Hideaki. Hisamoto

  DOI：10.1021/ac00098a016

  日期：1995.1.15

  The double-armed diazacrown ethers, which have a base diazacrown ether ring with two diamide-type side chains, were designed and synthesized on the basis of the proposed molecular model for the novel neutral Ca2+ and Mg2+ ionophores. The potentiometric ion-selective electrodes were prepared with over 20 kinds of systematically synthesized diazacrown ether derivatives. The relationship between the molecular structures of the ionophores and the ion selectivities was fully discussed. The electrodes based on the 21- and 18-membered diazacrown ether derivatives possessing a glycolic diamide and malonic diamide in their side chains (K23E1 and K22B5) exhibited excellent Ca2+ and Mg2+ selectivities, respectively. The ion-selectivity features of the novel Ca2+ and Mg2+ ionophores supply important structural information about the design of host molecules for alkaline earth metal cations.