cyclo[Azi(Me)(Me)-Phe-Gly-Leu-Sar] | 1569904-09-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: cyclo[Azi(Me)(Me)-Phe-Gly-Leu-Sar]
• 英文别名: (6S,12S,15S,16S)-12-benzyl-4,16-dimethyl-6-(2-methylpropyl)-1,4,7,10,13-pentazabicyclo[13.1.0]hexadecane-2,5,8,11,14-pentone
• CAS: 1569904-09-1
• 化学式: C₂₄H₃₃N₅O₅
• 分子量: 471.557
• InChiKey: GJPBSKMKQOEDAE-ULKUVHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cyclo[Azi(Me)(Me)-Phe-Gly-Leu-Sar] 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以4 mg的产率得到(3S,9S,12S)-12-((R)-1-azidoethyl)-9-benzyl-3-isobutyl-1-methyl-1,4,7,10,13-pentaazacyclopentadecane-2,5,8,11,14-pentaone
  参考文献：
  名称：

  Site-Specific Integration of Amino Acid Fragments into Cyclic Peptides

  摘要：

  The concept of site-specific integration of fragments into macrocyclic entities has not yet found application in the realm of synthetic chemistry. Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the site-specific integration of amino acids and peptide fragments into the homodetic cyclic peptide architecture. This new synthetic operation improves both the convergence and divergence of cyclic peptide synthesis.

  DOI：

  10.1021/ja412256f
• 作为产物：
  描述：

  lithium (S)-4-methyl-2-(2-((S)-2-((2S,3S)-3-methylaziridine-2-carboxamido)-3-phenylpropanamido)acetamido)pentanoate 在 N,N-二异丙基乙胺 、 (1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium hexafluoro-lambda5-phosphanuide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 cyclo[Azi(Me)(Me)-Phe-Gly-Leu-Sar]
  参考文献：
  名称：

  Site-Specific Integration of Amino Acid Fragments into Cyclic Peptides

  摘要：

  The concept of site-specific integration of fragments into macrocyclic entities has not yet found application in the realm of synthetic chemistry. Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the site-specific integration of amino acids and peptide fragments into the homodetic cyclic peptide architecture. This new synthetic operation improves both the convergence and divergence of cyclic peptide synthesis.

  DOI：

  10.1021/ja412256f

文献信息

• Site-Specific Integration of Amino Acid Fragments into Cyclic Peptides
  作者：Christopher J. White、Jennifer L. Hickey、Conor C. G. Scully、Andrei K. Yudin

  DOI：10.1021/ja412256f

  日期：2014.3.12

  The concept of site-specific integration of fragments into macrocyclic entities has not yet found application in the realm of synthetic chemistry. Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the site-specific integration of amino acids and peptide fragments into the homodetic cyclic peptide architecture. This new synthetic operation improves both the convergence and divergence of cyclic peptide synthesis.