(+)-2-acetamido-3-azidopropanoic acid methyl ester | 171514-07-1

• 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: (+)-2-acetamido-3-azidopropanoic acid methyl ester
• 英文别名: methyl (+)-2-acetamido-3-azidopropanoate；(S)-methyl 2-acetamido-3-azidopropanoate；methyl (2S)-2-acetamido-3-azidopropanoate
• CAS: 171514-07-1
• 化学式: C₆H₁₀N₄O₃
• 分子量: 186.17
• InChiKey: BGWQHVZRSCGRMP-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  104.16
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+)-2-acetamido-3-azidopropanoic acid methyl ester 在 copper(I) sulfate 、 sodium ascorbate 、 lithium hydroxide 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 2-乙酰氨基丙烯酸
  参考文献：
  名称：

  Stable triazolylphosphonate analogues of phosphohistidine

  摘要：

  Histidine-phosphorylated proteins and the corresponding kinases are important components of bacterial and eukaryotic cell-signalling pathways, and are therefore potential drug targets. The study of these biomolecules has been hampered by the lability of the phosphoramidate functional group in the phosphohistidines and the lack of generic antibodies. Herein, the design and concise synthesis of stable triazolylphosphonate analogues of N1- and N3-phosphohistidine, and derivatives suitable for bioconjugation, are described.

  DOI：

  10.1007/s00726-011-1145-2
• 作为产物：
  描述：

  N-乙酰-L-丝氨酸甲酯 在 hydrogen azide 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 以60%的产率得到(+)-2-acetamido-3-azidopropanoic acid methyl ester
  参考文献：
  名称：

  Stable triazolylphosphonate analogues of phosphohistidine

  摘要：

  Histidine-phosphorylated proteins and the corresponding kinases are important components of bacterial and eukaryotic cell-signalling pathways, and are therefore potential drug targets. The study of these biomolecules has been hampered by the lability of the phosphoramidate functional group in the phosphohistidines and the lack of generic antibodies. Herein, the design and concise synthesis of stable triazolylphosphonate analogues of N1- and N3-phosphohistidine, and derivatives suitable for bioconjugation, are described.

  DOI：

  10.1007/s00726-011-1145-2

文献信息

• Regioselectivity of ring-opening reactions of optically active N-acetyl-2-methoxycarbonylaziridine
  作者：Maria Bucciarelli、Arrigo Forni、Irene Moretti、Fabio Prati、Giovanni Torre

  DOI：10.1016/0957-4166(95)00270-y

  日期：1995.8

  (S)-(-)-N-acetyl-2-methoxycarbonylaziridine 1 undergoes easy ring-opening by Bronsted acids or nucleophiles in the presence of a Lewis acid catalyst. The regioselectivity is not always exclusive, affording optically active alpha- and beta-aminoacids.
• Stereochemistry of nucleophilic ring-opening reactions of optically active N-acetyl-2-methoxycarbonylaziridine
  作者：Paolo Davoli、Arrigo Forni、Irene Moretti、Fabio Prati

  DOI：10.1016/0957-4166(95)00261-m

  日期：1995.8

  The S(N)2-like mechanism of the nucleophilic attack of sodium azide on (S)-(-)-N-acetyl-2-methoxycarbonylaziridine was verified through the chemical correlation of the ring-opening products with (S)-(+)- or (R)-(-)-2,3-diaminopropanoic acid monohydrochloride.