N-tert-butyloxycarbonyl D-proline-glycine methyl ester | 92132-25-7

• 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: N-tert-butyloxycarbonyl D-proline-glycine methyl ester
• 英文别名: ^tert-Boc-D-Pro-Gly-OMe；^t-Boc-D-Pro-Gly-OMe；Boc-(D)Pro-Gly-OMe；Boc-D-Pro-Gly-OMe；tert-butyl (2R)-2-[(2-methoxy-2-oxoethyl)carbamoyl]pyrrolidine-1-carboxylate
• CAS: 92132-25-7
• 化学式: C₁₃H₂₂N₂O₅
• 分子量: 286.328
• InChiKey: RNCFSKLCUPXAEU-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl D-proline-glycine methyl ester 在 三氟乙酸 作用下， 反应 2.0h， 生成 (R)-Methylprolylglycinate
  参考文献：
  名称：

  设计，合成和吲哚-3-羧酰胺双环哌嗪类似物作为新型大麻素CB1受体激动剂的结构-活性关系研究

  摘要：

  合成双环哌嗪衍生物作为N-烷基哌嗪的构象约束类似物，发现其为有效的CB1受体激动剂。CB1受体激动剂活性取决于双环系统手性中心的绝对构型。尽管构象约束不能保护化合物免受N-去烷基化作用的代谢，但发现一些双环类似物比不受约束的先导化合物更有效。化合物8b在体内显示出有效的抗伤害感受活性。

  DOI：

  10.1016/j.bmcl.2010.10.061
• 作为产物：
  描述：

  D-脯氨酸 在 1-羟基苯并三唑 、 三乙胺 、 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 13.0h， 生成 N-tert-butyloxycarbonyl D-proline-glycine methyl ester
  参考文献：
  名称：

  Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents

  摘要：

  This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe-Gly and Pro-Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through various non-covalent interactions in the solid state which can be directly correlated with their fibrillation event in solution phase. Interestingly microscopic observations revealed that the amyloidogenic dipeptide constituents assembled into hollow tubular structures whereas the elastomeric dipeptide constituents assembled into the feather or sheet like structures. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.07.022

文献信息

• Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling
  作者：Byoungmoo Kim、Alex J. Chinn、Daniel R. Fandrick、Chris H. Senanayake、Robert A. Singer、Scott J. Miller

  DOI：10.1021/jacs.6b03444

  日期：2016.6.29

  guanidine-containing peptides as multifunctional ligands for transition-metal catalysis and its application in the remote desymmetrization of diarylmethanes via copper-catalyzed Ullman cross-coupling. Through design of these peptides, high levels of enantioinduction and good isolated yields were achieved in the long-range asymmetric cross-coupling (up to 93:7 er and 76% yield) between aryl bromides and malonates

  我们报道了一类新型含胍肽作为过渡金属催化多功能配体的开发及其在通过铜催化乌尔曼交叉偶联二芳基甲烷远程去对称化中的应用。通过这些肽的设计，芳基溴和丙二酸之间的长程不对称交叉偶联（高达 93:7 er 和 76% 产率）实现了高水平的对映诱导和良好的分离产率。我们的机制研究表明，远端立体控制是通过肽的路易斯碱性C端羧酸酯与底物的远端芳烃之间的Cs桥相互作用来实现的。
• 3-Triphenylphosphonio-2,5-piperazinediones as new chiral glycine cation equivalents
  作者：Tadeusz Gorewoda、Roman Mazurkiewicz、Wojciech Simka、Grzegorz Mlostoń、Grzegorz Schroeder、Maciej Kubicki、Nikodem Kuźnik

  DOI：10.1016/j.tetasy.2011.05.002

  日期：2011.4

  3-Triphenylphosphonio-2,5-piperazinediones were effectively synthesized from homochiral valine or proline via Boc-Val-Gly-OMe, Boc-Pro-Gly-OMe or Cbz-Pro-Gly-OMe. Retention of configuration of the primary stereogenic center of the valine and proline moieties was observed. Diastereoselective nucleophilic substitution of the triphenylphosphonium group in 2,5-piperazinediones with S-, N-, P- and C-nucleophiles was observed. The configuration of the substitution products was assigned either by their hydrolysis and decarboxylation or based on the analysis of the H-C(3)-N-H coupling constants of 3-substituted-2,5-piperazinediones derived from proline. The trans-stereoselectivity was predominant in reactions of 3-triphenylphosphonio-1,6-trimethylene-2,5-piperazinediones with the nucleophiles investigated. The stereodifferentiating ability of the proline moiety is much stronger than that of the valine unit and allowed nucleophilic alpha-functionalization of the glycine moiety with good to excellent diastereoselectivity. (C) 2011 Elsevier Ltd. All rights reserved.
• Bioinspired Modular Synthesis of Elastin-Mimic Polymers To Probe the Mechanism of Elastin Elasticity
  作者：Yulin Chen、Zhibin Guan

  DOI：10.1021/ja9104446

  日期：2010.4.7

  Bioinspired modular synthesis of elastin-mimic polymers (EMPs) is achieved via Cu-catalyzed alkyne-azide cyclization (CuAAC). By changing the module, EMPs with different secondary structures determined by circular dichroism (CD) spectra in trifluoroethanol (TFE) solution are obtained. The EMPs are characterized by measuring the lower critical solution temperatures (LSCTs) and the bulk mechanic properties under the conditions of both dry and hydrated forms. The unique molecular design enables us to probe mechanistic questions and assess the structure-property relationship of the EMPs. Our results indicate that, instead of a highly organized secondary structure, hydrophobic hydration is critical for the elasticity of EMPs.
• NEUBERT, K.;HARTRODT, B.;BARTH, A.;MATTHIES, H. -J.
  作者：NEUBERT, K.、HARTRODT, B.、BARTH, A.、MATTHIES, H. -J.

  DOI：——

  日期：——
• Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents
  作者：Vikas Kumar、K. Vijaya Krishna、Shruti Khanna、Khashti Ballabh Joshi

  DOI：10.1016/j.tet.2016.07.022

  日期：2016.9

  This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe-Gly and Pro-Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through various non-covalent interactions in the solid state which can be directly correlated with their fibrillation event in solution phase. Interestingly microscopic observations revealed that the amyloidogenic dipeptide constituents assembled into hollow tubular structures whereas the elastomeric dipeptide constituents assembled into the feather or sheet like structures. (C) 2016 Elsevier Ltd. All rights reserved.