(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino-15N)-6-(2-(((tert-butyldimethylsilyl)oxy)methyl)-5-formyl-1H-pyrrol-1-yl-1-15N)hexanoic-1,2,3,4,5,6-13C6 acid | 1456895-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino-15N)-6-(2-(((tert-butyldimethylsilyl)oxy)methyl)-5-formyl-1H-pyrrol-1-yl-1-15N)hexanoic-1,2,3,4,5,6-13C6 acid
• CAS: 1456895-18-3
• 化学式: C₃₃H₄₂N₂O₆Si
• 分子量: 598.712
• InChiKey: APEKGBRQQMBOPQ-VNKKWPMMSA-N

物化性质

• 熔点：
  40 °C

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  106.86
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino-15N)-6-(2-(((tert-butyldimethylsilyl)oxy)methyl)-5-formyl-1H-pyrrol-1-yl-1-15N)hexanoic-1,2,3,4,5,6-13C6 acid 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以96%的产率得到
  参考文献：
  名称：

  Synthesis of stable isotope-labelled monolysyl advanced glycation endproducts

  摘要：

  Advanced Glycation Endproducts (AGEs) are modified amino acids that form on proteins and are known to be implicated in the pathogenesis of diabetes and related diseases. Ready access to synthetic stable isotope-labelled AGEs allows for quantitative mass spectrometry studies to be undertaken, providing key insights into the roles AGEs play in the progression of such diseases. However, the majority of current syntheses of these compounds suffer from poor yields and lengthy procedures and are not suitable for the purposes required here. Here, we report robust syntheses of stable isotope-labelled monolysyl AGEs, N-epsilon-(carboxymethyl)lysine, N-epsilon-(carboxyethyl)lysine and pyrraline, that provide straightforward access to these compounds for quantitative amino acid analysis. This work will facilitate future investigations with these compounds and lead to a better understanding of the roles they play in diabetes and related diseases.

  DOI：

  10.1007/s00726-013-1498-9
• 作为产物：
  描述：

  6-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2H-pyran-3(6H)-one 、 (((9H-fluoren-9-yl)methoxy)carbonyl)-L-lysine-13C6-15N2 compound with 2,2,2-trifluoroacetic acid (1:1) 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以54%的产率得到(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino-15N)-6-(2-(((tert-butyldimethylsilyl)oxy)methyl)-5-formyl-1H-pyrrol-1-yl-1-15N)hexanoic-1,2,3,4,5,6-13C6 acid
  参考文献：
  名称：

  Synthesis of stable isotope-labelled monolysyl advanced glycation endproducts

  摘要：

  Advanced Glycation Endproducts (AGEs) are modified amino acids that form on proteins and are known to be implicated in the pathogenesis of diabetes and related diseases. Ready access to synthetic stable isotope-labelled AGEs allows for quantitative mass spectrometry studies to be undertaken, providing key insights into the roles AGEs play in the progression of such diseases. However, the majority of current syntheses of these compounds suffer from poor yields and lengthy procedures and are not suitable for the purposes required here. Here, we report robust syntheses of stable isotope-labelled monolysyl AGEs, N-epsilon-(carboxymethyl)lysine, N-epsilon-(carboxyethyl)lysine and pyrraline, that provide straightforward access to these compounds for quantitative amino acid analysis. This work will facilitate future investigations with these compounds and lead to a better understanding of the roles they play in diabetes and related diseases.

  DOI：

  10.1007/s00726-013-1498-9