Boc-Hse-Pro-OMe | 159830-98-5

• 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: Boc-Hse-Pro-OMe
• 英文别名: methyl (2S)-1-[(2S)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]pyrrolidine-2-carboxylate
• CAS: 159830-98-5
• 化学式: C₁₅H₂₆N₂O₆
• 分子量: 330.381
• InChiKey: RBBUHBWWXJZZEU-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Hse-Pro-OMe 在 tetrabutylammonium tetrafluoroborate 作用下， 以 异丙醇 、 乙腈 为溶剂， 以48%的产率得到(3S,7S,10S)-3-((tert-butyloxycarbonyl)amino)-10-(methoxycarbonyl)-1-aza-6-oxa-2-oxobicyclo<5.3.0>decane
  参考文献：
  名称：

  阳极酰胺氧化：二肽直接氧化的构象受限的肽结构单元

  摘要：

  通过二肽的直接阳极氧化以高收率合成了一对基于双环内酰胺的构象受限的肽模拟物。这项工作突出了使用电化学来构建肽模拟物的简便性，并进一步定义了与环化成氨基酸衍生物的电化学方法兼容的取代基的性质。

  DOI：

  10.1016/0040-4039(94)88206-1
• 作为产物：
  描述：

  Boc-Hse(Bzl)-Pro-OMe 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以77%的产率得到Boc-Hse-Pro-OMe
  参考文献：
  名称：

  Electrochemical Cyclization of Dipeptides toward Novel Bicyclic, Reverse-Turn Peptidomimetics. 1. Synthesis and Conformational Analysis of 7,5-Bicyclic Systems

  摘要：

  Novel, highly constrained, 7,5-bicyclic dipeptides (1-aza-6-oxa-2-oxobicyclo[5.3.0]decane ring skeletons, 3Sa and 7Sa) have been synthesized on a 40 mmol scale in similar to 50% yield by a one-step electrochemical cyclization from the dipeptides Boc-L-homoserine-L-proline-OMe (Boc-Hse-Pro-OMe) and Boc-Hse-D-Pro-OMe. The reaction involved a selective anodic amide oxidation which was highly diastereoselective, generating a new chiral center having an S configuration from both precursors. In terms of conformation, the bicyclic system restricts two (psi 2 and phi 3) of the four torsion angles that characterize a reverse turn. Conformational analysis of these molecules and analogs having an R configuration at the ring fusion revealed some families of minimum energy conformations with torsion angles close to those of classical beta-turns, a secondary structural feature found in many bioactive peptides. This new ring skeleton was stable to trifluoroacetic acid, dilute base, and anhydrous hydrofluoric acid, making it compatible with standard solid phase peptide synthesis methodologies.

  DOI：

  10.1021/ja00108a007

文献信息

• Building Functionalized Peptidomimetics:  Use of Electroauxiliaries for Introducing <i>N</i>-Acyliminium Ions into Peptides
  作者：Haizhou Sun、Connor Martin、David Kesselring、Rebecca Keller、Kevin D. Moeller

  DOI：10.1021/ja064737l

  日期：2006.10.1

  A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.