cyclo[-Val-Ser(ψ-^Me,Mepro)-Val-Ser(ψ-^Me,Mepro)-] | 1235394-69-0

• 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[-Val-Ser(ψ-^Me,Mepro)-Val-Ser(ψ-^Me,Mepro)-]
• 英文别名: (3S,6S,12S,15S)-9,9,18,18-tetramethyl-3,12-di(propan-2-yl)-8,17-dioxa-1,4,10,13-tetrazatricyclo[13.3.0.06,10]octadecane-2,5,11,14-tetrone
• CAS: 1235394-69-0
• 化学式: C₂₂H₃₆N₄O₆
• 分子量: 452.551
• InChiKey: WGFAABSYBAZTRC-VGWMRTNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cyclo[-Val-Ser(ψ-^Me,Mepro)-Val-Ser(ψ-^Me,Mepro)-] 在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 96.0h， 以39%的产率得到cyclo[Val-Ser-Val-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
• 作为产物：
  描述：

  NH2-Val-Ser(ψ-Me,Mepro)-Val-Ser(ψ-Me,Mepro)-OH 在 4‐(4,6dimethoxy‐1,3,5‐triazin‐2‐yl)‐4‐methylmorpholinium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以60%的产率得到cyclo[-Val-Ser(ψ-^Me,Mepro)-Val-Ser(ψ-^Me,Mepro)-]
  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

• Synthesis of All-<scp>l</scp> Cyclic Tetrapeptides Using Pseudoprolines as Removable Turn Inducers
  作者：Kelly A. Fairweather、Nima Sayyadi、Ian J. Luck、Jack K. Clegg、Katrina A. Jolliffe

  DOI：10.1021/ol101018w

  日期：2010.7.16

  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.