cyclo[-Val-Thr-Val-Thr(ψ^Me,Mepro)-Val-Thr(ψ^Me,Mepro)-] | 820225-95-4

• 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-Thr-Val-Thr(ψ^Me,Mepro)-Val-Thr(ψ^Me,Mepro)-]
• 英文别名: (3S,6S,7R,12S,15S,18S,21S,22R)-15-[(1R)-1-hydroxyethyl]-7,9,9,22,24,24-hexamethyl-3,12,18-tri(propan-2-yl)-8,23-dioxa-1,4,10,13,16,19-hexazatricyclo[19.3.0.06,10]tetracosane-2,5,11,14,17,20-hexone
• CAS: 820225-95-4
• 化学式: C₃₃H₅₆N₆O₉
• 分子量: 680.842
• InChiKey: DZRWCHCQFFMBNR-ZRNXLIBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  48
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  196
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  cyclo[-Val-Thr-Val-Thr(ψ^Me,Mepro)-Val-Thr(ψ^Me,Mepro)-] 在 咪唑 、 盐酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 108.0h， 生成 cyclo[-Val-Thr-Val-Thr-Val-Thr-]
  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 、 盐酸 、 lithium hydroxide 、 camphor-10-sulfonic acid 、 五氟苯基二苯基磷酸酯 、 四丁基氟化铵 、 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 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 33.0h， 生成 cyclo[-Val-Thr-Val-Thr(ψ^Me,Mepro)-Val-Thr(ψ^Me,Mepro)-]
  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.