(S)-2-[(2-oxo-2H-chromen-3-ylcarbonyl)amino]propanoic acid | 1063965-41-2

• 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: (S)-2-[(2-oxo-2H-chromen-3-ylcarbonyl)amino]propanoic acid
• 英文别名: N-(coumarin-3-ylcarbonyl)-L-Ala-OH；(2S)-2-[(2-oxochromene-3-carbonyl)amino]propanoic acid
• CAS: 1063965-41-2
• 化学式: C₁₃H₁₁NO₅
• mdl: MFCD10699933
• 分子量: 261.234
• InChiKey: HZGWSDNGFXQHSB-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-[(2-oxo-2H-chromen-3-ylcarbonyl)amino]propanoic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Novel emissive bio-inspired non-proteinogenic coumarin-alanine amino acid: fluorescent probe for polyfunctional systems

  摘要：

  Two new bio-inspired non-proteinogenic compounds L1 and L2, containing coumarin and/or acridine chromophores and bearing as spacer an alanine amino acid were successfully synthesized and fully characterized by elemental analysis, H-1 and C-13 NMR, infrared spectroscopy (KBr discs), melting point, ESI-TOF (electrospray ionization-time of flight-mass), UV-vis absorption and emission spectroscopy, fluorescence quantum yields and lifetime measurements. A relative fluorescence quantum yield of 0.02 was determined for both compounds. In L2 the presence of an intramolecular energy transfer from the coumarin to the acridine unit was observed. L1 and L2 are quite sensitive to the basicity of the environment. At alkaline values both compounds show a strong quenching in the fluorescence emission, attributed to the photoinduced electron transfer (PET). However, both deprotonated forms recover the emission with the addition of Zn2+, Cd2+ and Al3+ metal ions. As multifunctional emissive probes, the titration of L1 and L2 with lanthanides (III), Eu3+ and Tb3+ was also explored as new visible bio-probes in the absence and in the presence of liposomes. In a liposomal environment a lower energy transfer was observed.

  DOI：

  10.1007/s00726-012-1262-6
• 作为产物：
  描述：

  methyl-2-[(2-oxo-2H-1-benzopyran-3-carbonyl)amino]propanoate 在 sodium hydroxide 、 potassium hydrogensulfate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (S)-2-[(2-oxo-2H-chromen-3-ylcarbonyl)amino]propanoic acid
  参考文献：
  名称：

  Novel emissive bio-inspired non-proteinogenic coumarin-alanine amino acid: fluorescent probe for polyfunctional systems

  摘要：

  Two new bio-inspired non-proteinogenic compounds L1 and L2, containing coumarin and/or acridine chromophores and bearing as spacer an alanine amino acid were successfully synthesized and fully characterized by elemental analysis, H-1 and C-13 NMR, infrared spectroscopy (KBr discs), melting point, ESI-TOF (electrospray ionization-time of flight-mass), UV-vis absorption and emission spectroscopy, fluorescence quantum yields and lifetime measurements. A relative fluorescence quantum yield of 0.02 was determined for both compounds. In L2 the presence of an intramolecular energy transfer from the coumarin to the acridine unit was observed. L1 and L2 are quite sensitive to the basicity of the environment. At alkaline values both compounds show a strong quenching in the fluorescence emission, attributed to the photoinduced electron transfer (PET). However, both deprotonated forms recover the emission with the addition of Zn2+, Cd2+ and Al3+ metal ions. As multifunctional emissive probes, the titration of L1 and L2 with lanthanides (III), Eu3+ and Tb3+ was also explored as new visible bio-probes in the absence and in the presence of liposomes. In a liposomal environment a lower energy transfer was observed.

  DOI：

  10.1007/s00726-012-1262-6

文献信息

• Chiral <i>N</i>-(Coumarin-3-ylcarbonyl)-α-amino Acids: Fluorescent Markers for Amino Acids and Dipeptides
  作者：Alan Katritzky、Tamari Narindoshvili、Parul Angrish

  DOI：10.1055/s-2008-1067078

  日期：——

  N-(Coumarin-3-ylcarbonyl)benzotriazole has been coupled with free amino acids, N-terminal-protected lysines and dipeptides to afford fluorescent amino acids and dipeptides (76-89% yield) with retention of original chirality. N α - and N e -Coumarin-labeled- lysines are obtained by simple, two-step procedures. N α -Cbz- N e -(Coumarin-3-ylcarbonyl)- L-lysine is demonstrated to be an optically active

  N-(Coumarin-3-ylcarbonyl)benzotriazole 已与游离氨基酸、N-末端保护的赖氨酸和二肽偶联，以提供荧光氨基酸和二肽（产率 76-89%），并保留原始手性。N α - 和 N e -香豆素标记的赖氨酸通过简单的两步程序获得。N α -Cbz- N e -(Coumarin-3-ylcarbonyl)-L-lysine 被证明是一种光学活性荧光标记，用于在溶液相合成中标记氨基酸。
• Fluorescent-Labeled Amino Acid–Antibiotic Conjugates
  作者：Siva Panda、C. Hall、Anand Tiwari、Abdullah Asiri、Alan Katritzky

  DOI：10.1055/s-0033-1340193

  日期：——