Z-(R)-Ala-(S)-Phe-OMe | 28944-95-8

• 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-(R)-Ala-(S)-Phe-OMe
• 英文别名: Z-D-Ala-Phe-OMe；N-Cbz-D-Ala-L-Phe-OMe；Z-D-Ala-L-Phe-OMe；methyl (2S)-3-phenyl-2-[[(2R)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 28944-95-8
• 化学式: C₂₁H₂₄N₂O₅
• 分子量: 384.432
• InChiKey: SIHNOQQFBTTYLO-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-(R)-Ala-(S)-Phe-OMe 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以81%的产率得到N-[N-[(苯基甲氧基)羰基]-D-丙氨酰]-L-苯丙氨酸
  参考文献：
  名称：

  与组蛋白脱乙酰基酶抑制有关的环状四肽的模块化方法：表微孢子素A的合成

  摘要：

  使用交叉复分解反应作为关键步骤，已经开发出一条短的新途径，可以开发出一些重要的HDAC抑制剂的不寻常氨基酸成分（S）-2-氨基-8-氧代十二烷酸（Aoda）。已证明对通过交叉复分解接枝大环骨架的研究的扩展对合成环状四肽HDAC抑制剂微孢子素的异构体非常有效。

  DOI：

  10.1016/j.tetlet.2016.01.005
• 作为产物：
  描述：

  N-CBZ-DL-丙氨酸 、 L-苯丙氨酸甲酯盐酸盐 在 N-甲基吗啉 、 DMT*brucine tetrafluoroborate 、 马钱子碱 作用下， 以 乙腈 为溶剂， 以94%的产率得到Z-(R)-Ala-(S)-Phe-OMe
  参考文献：
  名称：

  Design, Synthesis, and Application of Enantioselective Coupling Reagent with a Traceless Chiral Auxiliary

  摘要：

  Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure of a chiral auxiliary after the activation of the carboxylic function, all of the subsequent stages of the coupling reaction proceed without any perturbation caused by a chirality discriminator (traceless). Therefore, the advantageous coupling conditions, configuration, and enantiomeric purity of the final product are entirely predictable from the model experiment.

  DOI：

  10.1021/ol802691x

文献信息

• The design, synthesis, and application of a chiral coupling reagent derived from strychnine for the enantioselective activation of a carboxylic group
  作者：Beata Kolesińska、Katarzyna Kasperowicz、Marek Sochacki、Adam Mazur、Stefan Jankowski、Zbigniew J. Kamiński

  DOI：10.1016/j.tetlet.2009.06.105

  日期：2010.1

  The concept of a chiral coupling reagent for the enantioselective synthesis of peptides with a predictable configuration and enantiomeric purity from racemic substrates is presented. The reagent was prepared by treatment of strychninium tetrafluoroborate with 2-chloro-4,6-dimethoxy-1,3,5-triazine in the presence of sodium bicarbonate yielding N-(4,6-dimethoxy-1,3,5-triazin-2-yl)strychninium tetrafluoroborate

  提出了用于从外消旋底物中对映体选择性合成具有可预测构型和对映体纯度的肽的手性偶联剂的概念。在碳酸氢钠存在下，用2-氯-4,6-二甲氧基-1,3,5-三嗪处理四氟硼酸锶，制备N-（4,6-二甲氧基-1,3,5-三嗪。 -2-基）四氟硼酸锶在室温下稳定，在多种溶剂中均能以d的高收率高收率得到富集的Z-Ala-Phe-OMe（dr从95/5至60/40）从rac -Z-Ala-OH开始的丙氨酸残基的-构型。
• The method of preparation of enantiomerically enriched products of condensation from racemic acids or acids of the low enentiomeric purity
  申请人：Politechnika Lódzka

  公开号：EP2418190B1

  公开（公告）日：2013-08-28
• Zajac, Krzysztof; Kaminski, Zbigniew J., Acta poloniae pharmaceutica, 2010, vol. 67, # 6, p. 725 - 728
  作者：Zajac, Krzysztof、Kaminski, Zbigniew J.

  DOI：——

  日期：——
• Design, Synthesis, and Application of Enantioselective Coupling Reagent with a Traceless Chiral Auxiliary
  作者：Beata Kolesinska、Zbigniew J. Kaminski

  DOI：10.1021/ol802691x

  日期：2009.2.5

  Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure of a chiral auxiliary after the activation of the carboxylic function, all of the subsequent stages of the coupling reaction proceed without any perturbation caused by a chirality discriminator (traceless). Therefore, the advantageous coupling conditions, configuration, and enantiomeric purity of the final product are entirely predictable from the model experiment.
• A modular approach to cyclic tetrapeptides related to histone deacetylase inhibition: synthesis of epi-microsporin A
  作者：Jyoti Prasad Mukherjee、Suman Sil、Shital K. Chattopadhyay

  DOI：10.1016/j.tetlet.2016.01.005

  日期：2016.2

  A short new route to the unusual amino acid component (S)-2-amino-8-oxodecanoic acid (Aoda) of some important HDAC inhibitors has been developed using cross metathesis reaction as the key step. An extension of the study employing grafting of a macrocyclic scaffold through cross metathesis has proved to be highly efficient for the synthesis of an isomer of the cyclic tetrapeptide HDAC inhibitor microsporin

  使用交叉复分解反应作为关键步骤，已经开发出一条短的新途径，可以开发出一些重要的HDAC抑制剂的不寻常氨基酸成分（S）-2-氨基-8-氧代十二烷酸（Aoda）。已证明对通过交叉复分解接枝大环骨架的研究的扩展对合成环状四肽HDAC抑制剂微孢子素的异构体非常有效。