Val-Thr(ψ^Me,Mepro)-Val-Thr(ψ^Me,Mepro)-Val-Thr(TBS)-OH | 820225-77-2

• 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: Val-Thr(ψ^Me,Mepro)-Val-Thr(ψ^Me,Mepro)-Val-Thr(TBS)-OH
• 英文别名: (2S,3R)-2-[[(2S)-2-[[(4S,5R)-3-[(2S)-2-[[(4S,5R)-3-[(2S)-2-amino-3-methylbutanoyl]-2,2,5-trimethyl-1,3-oxazolidine-4-carbonyl]amino]-3-methylbutanoyl]-2,2,5-trimethyl-1,3-oxazolidine-4-carbonyl]amino]-3-methylbutanoyl]amino]-3-[tert-butyl(dimethyl)silyl]oxybutanoic acid
• CAS: 820225-77-2
• 化学式: C₃₉H₇₂N₆O₁₀Si
• 分子量: 813.12
• InChiKey: YTPVXXPJOFLOLV-OHZHDGOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  219
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Val-Thr(ψ^Me,Mepro)-Val-Thr(ψ^Me,Mepro)-Val-Thr(TBS)-OH 在 盐酸 、 五氟苯基二苯基磷酸酯 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 72.0h， 生成 (3S,6S,9S,12S,15R,18S)-3,9,15-Tris-((R)-1-hydroxy-ethyl)-6,12,18-triisopropyl-1,4,7,10,13,16-hexaaza-cyclooctadecane-2,5,8,11,14,17-hexaone
  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 palladium on activated charcoal N-甲基吗啉 、 lithium hydroxide 、 camphor-10-sulfonic acid 、 氢气 、 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 27.0h， 生成 Val-Thr(ψ^Me,Mepro)-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.