Z-Val-Thr(TBS)-Val-Thr(ψ^Me,Mepro)-Val-Thr(TBS)-OH | 820226-02-6

• 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: Z-Val-Thr(TBS)-Val-Thr(ψ^Me,Mepro)-Val-Thr(TBS)-OH
• 英文别名: (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-2-[[(4S,5R)-3-[(2S)-2-[[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]butanoyl]amino]-3-methylbutanoyl]-2,2,5-trimethyl-1,3-oxazolidine-4-carbonyl]amino]-3-methylbutanoyl]amino]butanoic acid
• CAS: 820226-02-6
• 化学式: C₅₀H₈₈N₆O₁₂Si₂
• 分子量: 1021.45
• InChiKey: PPLKWHKHMSDGNH-PHFDWKNKSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  1044.7±65.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  70
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  240
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Z-Val-Thr(TBS)-Val-Thr(ψ^Me,Mepro)-Val-Thr(TBS)-OH 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以96%的产率得到Val-Thr(TBS)-Val-Thr(ψ^Me,Mepro)-Val-Thr(TBS)-OH
  参考文献：
  名称：

  Pseudoprolines as Removable Turn Inducers:  Tools for the Cyclization of Small Peptides

  摘要：

  The cyclization of small peptides which do not incorporate turn inducers is often difficult. We have developed a method involving the use of removable turn inducers, in the form of pseudoprolines, for the cyclization of difficult peptide sequences. The pseudoprolines induce a cisoid amide bond in the peptide backbone which facilitates cyclization. They are then readily removed to yield a cyclic peptide that does not contain any turn inducers.

  DOI：

  10.1021/jo0484732
• 作为产物：
  描述：

  Cbz-Val-Thr-OMe 在 N-甲基吗啉 、 咪唑 、 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 Z-Val-Thr(TBS)-Val-Thr(ψ^Me,Mepro)-Val-Thr(TBS)-OH
  参考文献：
  名称：

  Pseudoprolines as Removable Turn Inducers:  Tools for the Cyclization of Small Peptides

  摘要：

  The cyclization of small peptides which do not incorporate turn inducers is often difficult. We have developed a method involving the use of removable turn inducers, in the form of pseudoprolines, for the cyclization of difficult peptide sequences. The pseudoprolines induce a cisoid amide bond in the peptide backbone which facilitates cyclization. They are then readily removed to yield a cyclic peptide that does not contain any turn inducers.

  DOI：

  10.1021/jo0484732

文献信息

• Pseudoprolines as Removable Turn Inducers:  Tools for the Cyclization of Small Peptides
  作者：Danielle Skropeta、Katrina A. Jolliffe、Peter Turner

  DOI：10.1021/jo0484732

  日期：2004.12.1

  The cyclization of small peptides which do not incorporate turn inducers is often difficult. We have developed a method involving the use of removable turn inducers, in the form of pseudoprolines, for the cyclization of difficult peptide sequences. The pseudoprolines induce a cisoid amide bond in the peptide backbone which facilitates cyclization. They are then readily removed to yield a cyclic peptide that does not contain any turn inducers.