N-[N-(N-(1-oxoprop-2-yne)-L-leucyl)glycyl]glycine methyl ester | 1301605-68-4

• 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: N-[N-(N-(1-oxoprop-2-yne)-L-leucyl)glycyl]glycine methyl ester
• CAS: 1301605-68-4
• 化学式: C₁₄H₂₁N₃O₅
• 分子量: 311.338
• InChiKey: YJTSYDLNEOLXOD-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.44
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  113.6
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-azido-N-[3-(fluorobis(1-methylethyl)silyl)propyl]propanamide 、 N-[N-(N-(1-oxoprop-2-yne)-L-leucyl)glycyl]glycine methyl ester 在 copper diacetate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 18.0h， 以40%的产率得到methyl (1-(3-((3-(fluorodiisopropylsilyl)propyl)amino)-3-oxopropyl)-1H-1,2,3-triazole-4-carbonyl)-L-leucylglycylglycinate
  参考文献：
  名称：

  Synthesis and hydrolytic stability of novel 3-[18F]fluoroethoxybis(1-methylethyl)silyl]propanamine-based prosthetic groups

  摘要：

  Two new silicon-based prosthetic groups, derived from 3-[ethoxybis(1-methylethyl)silyl]propanamine, have been prepared in good yields. These silicon groups bearing an acid or an azide group were coupled to a model tripeptide (Leu-Gly-Gly) either through a classical amide bond formation or through "click chemistry" via the Huisgen cycloaddition. The radiolabelling with fluorine-18 by substitution of the ethoxy group at silicon has been carried out with success in 51-54% decay corrected radiochemical yields. Radiolabelled peptides were easily prepared by direct F-18-fluorination of the silicon-bearing tripeptide or by coupling the peptide with a radiolabelled silicon-based prosthetic group. Their stabilities in physiological medium were studied and proved poor. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.01.011
• 作为产物：
  描述：

  L-亮氨酰甘氨酰甘氨酸 在 potassium carbonate 、 1-羟基苯并三唑 、 乙酰氯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 N-[N-(N-(1-oxoprop-2-yne)-L-leucyl)glycyl]glycine methyl ester
  参考文献：
  名称：

  Synthesis and hydrolytic stability of novel 3-[18F]fluoroethoxybis(1-methylethyl)silyl]propanamine-based prosthetic groups

  摘要：

  Two new silicon-based prosthetic groups, derived from 3-[ethoxybis(1-methylethyl)silyl]propanamine, have been prepared in good yields. These silicon groups bearing an acid or an azide group were coupled to a model tripeptide (Leu-Gly-Gly) either through a classical amide bond formation or through "click chemistry" via the Huisgen cycloaddition. The radiolabelling with fluorine-18 by substitution of the ethoxy group at silicon has been carried out with success in 51-54% decay corrected radiochemical yields. Radiolabelled peptides were easily prepared by direct F-18-fluorination of the silicon-bearing tripeptide or by coupling the peptide with a radiolabelled silicon-based prosthetic group. Their stabilities in physiological medium were studied and proved poor. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.01.011