cyclo[Leu-Ser-Leu-Ser] | 1235394-78-1

• 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: cyclo[Leu-Ser-Leu-Ser]
• 英文别名: (3S,6S,9S,12S)-3,9-bis(hydroxymethyl)-6,12-bis(2-methylpropyl)-1,4,7,10-tetrazacyclododecane-2,5,8,11-tetrone
• CAS: 1235394-78-1
• 化学式: C₁₈H₃₂N₄O₆
• 分子量: 400.475
• InChiKey: ZVYFKFWQBSHCGV-XUXIUFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  cyclo[-Leu-Ser(ψ-^Me,Mepro)-Leu-Ser(ψ-^Me,Mepro)-] 在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 96.0h， 以79%的产率得到cyclo[Leu-Ser-Leu-Ser]
  参考文献：
  名称：

  Synthesis of All-l Cyclic Tetrapeptides Using Pseudoprolines as Removable Turn Inducers

  摘要：

  Cyclic tetrapeptides h we generated great interest because of their broad-ranging biological properties. In order to synthesize these highly strained 12-membered cyclic compounds, a cyclization strategy using pseudoprolines as removable turn inducers has been developed. The pseudoproline derivatives induce a cisoid amide bond in the linear peptide backbone which facilitates cyclization. After cyclization, the turn inducers can be readily removed to afford cyclic tetrapeptides containing serine or threonine residues.

  DOI：

  10.1021/ol101018w

文献信息

• Facile Synthesis of Peptidyl Salicylaldehyde Esters and Its Use in Cyclic Peptide Synthesis
  作者：Jun-Feng Zhao、Xiao-Hong Zhang、Ying-Jie Ding、Yong-Sheng Yang、Xiao-Bao Bi、Chuan-Fa Liu

  DOI：10.1021/ol402279h

  日期：2013.10.18

  An efficient solid phase synthetic protocol for salicylaldehyde ester peptides is reported. With a Ser or Thr at the N-terminus, these salicylaldehyde ester peptides can be easily converted to Ser/Thr containing cyclic peptides.

  报道了一种有效的水杨醛酯肽的固相合成方案。这些水杨醛酯肽在N端带有Ser或Thr，可以轻松转化为含Ser / Thr的环肽。