methyl N-benzyloxycarbonyl-aminoisobutyryl-L-prolinate | 15030-91-8

• 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: methyl N-benzyloxycarbonyl-aminoisobutyryl-L-prolinate
• 英文别名: N<α-(benzyloxycarbonylamino)isobutyryl>-L-proline methyl ester；Z-Aib-L-Pro-OMe；Z-Aib-Pro-OMe；methyl (2-(((benzyloxy)carbonyl)amino)-2-methylpropanoyl)-L-prolinate；α-Benzyloxycarbonyl-amino-isobutyryl-L-prolin-methylester；methyl (2S)-1-[2-methyl-2-(phenylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylate
• CAS: 15030-91-8
• 化学式: C₁₈H₂₄N₂O₅
• 分子量: 348.399
• InChiKey: QWLIHXFKZOAEMM-AWEZNQCLSA-N

物化性质

• 沸点：
  519.7±50.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl N-benzyloxycarbonyl-aminoisobutyryl-L-prolinate 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 Z-Aib-Pro-Aib-OMe
  参考文献：
  名称：

  嘧菌胺I的溶液相合成

  摘要：

  据报道通过溶液相法合成了总的丙乐霉素I。

  DOI：

  10.1016/s0040-4020(01)92061-7
• 作为产物：
  描述：

  氯甲酸苄酯 在 N-甲基吗啉 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 methyl N-benzyloxycarbonyl-aminoisobutyryl-L-prolinate
  参考文献：
  名称：

  在13 C-NMR-谱和新方法中合成pH值为2-甲基丙氨酸的肽

  摘要：

  通过13 C-NMR研究了不常见的氨基酸2-甲基丙氨酸（α-氨基异丁酸，Aib）。关于相邻基团和氨基酸，讨论了Aib的氨基或羧基保护的衍生物和受保护的寡肽的化学位移。研究了Aib，Aib-Ala，Ala-Aib，Aib-Ala-Aib和Aib-Ala-Aib-Ala-Aib的13 C-NMR光谱的pH依赖性。使用这些示例，首次展示了一种新的有利方法，用于评估NMR滴定曲线，该方法使用了所谓的化学位移图（CS图）。

  DOI：

  10.1016/0040-4020(82)85164-8

文献信息

• Synthesis of polycyclic aminal heterocycles <i>via</i> decarboxylative cyclisation of dipeptide derivatives
  作者：Emma G. L. Robert、Eliott Le Du、Jerome Waser

  DOI：10.1039/d2cc00167e

  日期：——

  An oxidative-decarboxylative intramolecular cyclisation of dipeptide derivatives is reported. This transformation is promoted by phenyl iodine(III) diacetate (PIDA) in combination with BF3·OEt2. The reaction gives access to a variety of valuable polycyclic N-heterocyclic scaffolds containing 5-, 6-, or 7-membered rings.

  报道了二肽衍生物的氧化脱羧分子内环化。苯碘( III )二乙酸酯(PIDA)与BF 3 ·OEt 2的组合促进了这种转化。该反应提供了获得各种有价值的多环 N-杂环支架的途径，这些支架包含 5-、6-或 7-元环。
• A kinetic method for detecting intramolecular peptide H-bonds
  作者：Erode N. Prabhakaran、Damodara N. Reddy、Shreya Banerjee

  DOI：10.1039/d1nj03544d

  日期：——

  The current method for the detection of peptide hydrogen bond (PHB) formation places charge donors/acceptors (D/A) at the N-/C-termini of the peptides involved in the putative PHB.

  目前检测肽氢键（PHB）形成的方法是将电荷给体/受体（D/A）放置在参与假定PHB的肽的N-/C-末端。
• 10.1002/recl.19941130904
  作者：Wijkmans, Jac C. H. M.、Kruijtzer, John A. W.、Marel, Gijs A. van der、Boom, Jacques H. van、Bloemhoff, Wim

  DOI：10.1002/recl.19941130904

  日期：——
• Synthesis and pharmacological evaluation of glycine-modified analogues of the neuroprotective agent glycyl-l-prolyl-l-glutamic acid (GPE)
  作者：Michelle Y.H. Lai、Margaret A. Brimble、David J. Callis、Paul W.R. Harris、Mark S. Levi、Frank Sieg

  DOI：10.1016/j.bmc.2004.10.004

  日期：2005.1

  The synthesis of 10 G*PE analogues, wherein the glycine residue has been modified, is described by coupling readily accessible dibenzyl-L-prolyl-L-glutamate 2 with various analogues of glycine. Pharmacological evaluation of the novel compounds was undertaken to further understand the role of the glycine residue on the observed neuroprotective properties of the endogenous tripeptide GPE. (C) 2004 Elsevier Ltd. All rights reserved.
• Impact of Dehydroamino Acids on the Structure and Stability of Incipient 3₁₀-Helical Peptides
  作者：Daniel Joaquin、Michael A. Lee、David W. Kastner、Jatinder Singh、Shardon T. Morrill、Gracie Damstedt、Steven L. Castle

  DOI：10.1021/acs.joc.9b02747

  日期：2020.2.7

  A comparative study of the impact of small, medium-sized, and bulky alpha,beta-dehydroamino acids (Delta AAs) on the structure and stability of Balarams incipient 3(10)-helical peptide (1) is reported. Replacement of the N-terminal Aib residue of 1 with a Delta AA afforded peptides 2a-c that maintained the 3(10)-helical shape of 1. In contrast, installation of a Delta AA in place of Aib-3 yielded peptides 3a-c that preferred a beta-sheet-like conformation. The impact of the Delta AA on peptide structure was independent of size, with small (Delta Ala), medium-sized (Z-Delta Abu), and bulky (Delta Val) Delta AAs exerting similar effects. The proteolytic stabilities of 1 and its analogs were determined by incubation with Pronase. Z-Delta Abu and Delta Val increased the resistance of peptides to proteolysis when incorporated at the 3-position and had negligible impact on stability when placed at the 1-position, whereas Delta Ala-containing peptides degraded rapidly regardless of position. Exposure of peptides 2a-c and 3a-c to the reactive thiol cysteamine revealed that Delta Ala-containing peptides underwent conjugate addition at room temperature, while Z-Delta Abu- and Delta Val-containing peptides were inert even at elevated temperatures. These results suggest that both bulky and more accessible medium-sized Delta AAs should be valuable tools for bestowing rigidity and proteolytic stability on bioactive peptides.