tert-butyl (2S)-4-amino-2-[[4-[[(2S)-4-amino-1-[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]amino]-6-[6-[[4,6-bis[[(2S)-4-amino-1-[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]amino]-1,3,5-triazin-2-yl]amino]hexylamino]-1,3,5-triazin-2-yl]amino]-4-oxobutanoate

• 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: tert-butyl (2S)-4-amino-2-[[4-[[(2S)-4-amino-1-[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]amino]-6-[6-[[4,6-bis[[(2S)-4-amino-1-[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]amino]-1,3,5-triazin-2-yl]amino]hexylamino]-1,3,5-triazin-2-yl]amino]-4-oxobutanoate
• 化学式: C₃₉H₃₅N₂O₃PolS
• 分子量: 1019.2
• InChiKey: DYFVKMMGKXLANR-CQJMVLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  72
• 可旋转键数：
  37
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  427
• 氢给体数：
  10
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  Fmoc-甘氨酸 、 tert-butyl (2S)-4-amino-2-[[4-[[(2S)-4-amino-1-[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]amino]-6-[6-[[4,6-bis[[(2S)-4-amino-1-[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]amino]-1,3,5-triazin-2-yl]amino]hexylamino]-1,3,5-triazin-2-yl]amino]-4-oxobutanoate 在 HATU 、 N,N-二异丙基乙胺 作用下， 反应 2.0h， 生成 Fmoc-(Et)Cys(Trt)-OBt
  参考文献：
  名称：

  Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method

  摘要：

  通过改进的N-烷基半胱氨酸(NAC)辅助硫酯化反应，采用传统的9-芴甲氧羰基(Fmoc)策略制备了肽段的芳基硫酯。含有C端NAC的肽段通过Fmoc策略制备，并通过4-巯基苯乙酸(MPAA)处理转化为芳基硫酯，过程中未发生显著的副反应。这种肽硫酯被用于高效制备95个氨基酸的趋化因子CCL27，采用无Ag+的硫酯方法。

  DOI：

  10.1039/b800884a
• 作为产物：
  描述：

  1,6-己二胺 、 tert-butyl (2S)-4-amino-2-[[4-[[(2S)-4-amino-1-[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]amino]-6-chloro-1,3,5-triazin-2-yl]amino]-4-oxobutanoate 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以26%的产率得到tert-butyl (2S)-4-amino-2-[[4-[[(2S)-4-amino-1-[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]amino]-6-[6-[[4,6-bis[[(2S)-4-amino-1-[(2-methylpropan-2-yl)oxy]-1,4-dioxobutan-2-yl]amino]-1,3,5-triazin-2-yl]amino]hexylamino]-1,3,5-triazin-2-yl]amino]-4-oxobutanoate
  参考文献：
  名称：

  A novel organogelator incorporating tert-butyl esters of asparagines

  摘要：

  我们合成了一种基于天冬酰胺叔丁酯的新型有机凝胶剂，并对其有机凝胶化能力进行了研究。流变学表征证实了其凝胶行为及其触变性能。此外，所进行的形态学研究还发现了其球形结构。因此，这种有机凝胶剂可被视为新出现的非纤维状凝胶的一个新例子。

  DOI：

  10.1039/b817565a

文献信息

• Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method
  作者：Hironobu Hojo、Yuichi Murasawa、Hidekazu Katayama、Tsuyoshi Ohira、Yuko Nakahara、Yoshiaki Nakahara

  DOI：10.1039/b800884a

  日期：——

  Aryl thioesters of peptide segments were prepared by the conventional 9-fluorenylmethoxycarbonyl (Fmoc) strategy using a novel N-alkyl cysteine (NAC)-assisted thioesterification reaction. The peptide carrying NAC at its C-terminus was prepared by the Fmoc strategy and converted to the aryl thioester by 4-mercaptophenylacetic acid (MPAA) treatment without significant side reactions. The peptide thioester was used for the efficient preparation of 95-amino acid (AA) chemokine CCL27 by an Ag+-free thioester method.

  通过改进的N-烷基半胱氨酸(NAC)辅助硫酯化反应，采用传统的9-芴甲氧羰基(Fmoc)策略制备了肽段的芳基硫酯。含有C端NAC的肽段通过Fmoc策略制备，并通过4-巯基苯乙酸(MPAA)处理转化为芳基硫酯，过程中未发生显著的副反应。这种肽硫酯被用于高效制备95个氨基酸的趋化因子CCL27，采用无Ag+的硫酯方法。
• A novel organogelator incorporating tert-butyl esters of asparagines
  作者：Virginia Lozano、Rebeca Hernández、Carmen Mijangos、María-Jesús Pérez-Pérez

  DOI：10.1039/b817565a

  日期：——

  A novel organogelator based on tert-butyl esters of asparagines has been synthesized and its organogelation abilities have been investigated. The rheological characterization has confirmed the gelation behavior, and its thixotropic properties. Furthermore, the morphological studies performed reveal a spherical structure. Thus, this organogelator can be considered as a new example of the emerging, but still reduced, list of gels with a non-fibrillar assembly.

  我们合成了一种基于天冬酰胺叔丁酯的新型有机凝胶剂，并对其有机凝胶化能力进行了研究。流变学表征证实了其凝胶行为及其触变性能。此外，所进行的形态学研究还发现了其球形结构。因此，这种有机凝胶剂可被视为新出现的非纤维状凝胶的一个新例子。
• Efficient Sequential Segment Coupling Using <i>N</i>-Alkylcysteine-Assisted Thioesterification for Glycopeptide Dendrimer Synthesis
  作者：Chinatsu Ozawa、Hidekazu Katayama、Hironobu Hojo、Yuko Nakahara、Yoshiaki Nakahara

  DOI：10.1021/ol801340m

  日期：2008.8.21

  A highly pure MUC1-derived glycopeptide dendrimer of 22 kDa was prepared by a sequential segment coupling, achieved by an N-alkylcysteine (NAC)-assisted thioesterification. The glycopeptide having C-terminal NAC was prepared by the Fmoc method and converted to the thioester 3-mercaptopgropionic acid treatment. The thioester was condensed with a lysine trimer carrying NAC to afford tetramer, which was then converted to the thioester. Two tetramers were condensed with ethylenediamine to give the octameric glycopeptide dendrimer.