(R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester | 157662-41-4

• 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: (R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester
• CAS: 157662-41-4
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: DAKUAGHAPOVLMY-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester 在 palladium on activated charcoal 2,2,6,6-tetramethylpiperidinyl-lithium 、 氢气 、 三乙胺 、 lithium diisopropyl amide 作用下， 反应 12.0h， 生成 ((6R,8aR)-8a-Isobutylcarbamoyl-5-oxo-octahydro-indolizin-6-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Dumas, Jean-Philippe; Germanas, Juris Paul, Tetrahedron Letters, 1994, vol. 35, # 10, p. 1493 - 1496

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-2-烯丙基吡咯烷-2-羧酸 在 四氧化锇 sodium periodate 作用下， 生成 (R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester
  参考文献：
  名称：

  Dumas, Jean-Philippe; Germanas, Juris Paul, Tetrahedron Letters, 1994, vol. 35, # 10, p. 1493 - 1496

  摘要：

  DOI：

文献信息

• Novel Bicyclic Lactams as XaaPro Type VI β Turn Mimics:  Design, Synthesis, and Evaluation
  作者：Kyonghee Kim、Jean-philippe Dumas、Juris P. Germanas

  DOI：10.1021/jo960012w

  日期：1996.1.1

  The design, enantioselective synthesis, and structural characterization of novel bicyclic lactams as peptide mimics of the type VI beta turn is described. The mimics duplicate the conformation of the backbone and disposition of the side-chain atoms of the central two residues of the turn. The Gly L-Pro mimic, lactam 6, was prepared in good overall yield starting from (S)-2-(2'-propenyl)proline. (1)H

  描述了新型双环内酰胺作为VIβ型转弯肽模拟物的设计，对映选择性合成和结构表征。该模拟物复制了骨架的构型和该匝的中心两个残基的侧链原子的布置。从（S）-2-（2'-丙烯基）脯氨酸开始，以良好的总收率制备了Gly L-Pro模拟物内酰胺6。（1）1 H NMR光谱确定了内酰胺六元环的取代基的相对立体化学和构象特征；X射线晶体学分析证实了构象和立体化学分配。对内酰胺6的晶体结构的检查表明，中央酰胺键明显扭曲出平面度。酰胺键的扭曲归因于在两个环的交界处存在sp（2）-杂化氮原子而导致的角度应变。内酰胺6的N，N-二甲基甲am衍生物的烯醇化物与苄基溴的烷基化选择性地提供了甲am11，其为VI-turn构型的L-Phe L-Pro二肽的模拟物。高度合成的模拟肽（例如11）的有效合成途径将在肽结构功能研究中被证明非常有用。
• Constrained Peptidomimetics for TRH: cis-Peptide Bond Analogs
  作者：Yunsong Tong、Jacek Olczak、Janusz Zabrocki、Marvin C Gershengorn、Garland R Marshall、Kevin D Moeller

  DOI：10.1016/s0040-4020(00)00886-3

  日期：2000.12

  Two constrained analogs of the tripeptide hormone thyroliberin (TRH) have been synthesized. In both, the HisPro peptide bond of the hormone has been 'locked' into a cis-conformation. In the first analog, the constraint used was identical to the constraint used in an earlier trans-peptide bond analog that was a potent agonist for the TRH endocrine receptor TRH-R-1. The second analog was built in order to take advantage of a tetrazole ring as the cis-peptide bond constraint. Neither analog showed agonist or antagonist behavior toward TRH-R1 suggesting that the cis-peptide bond conformation may not play a role in the affinity of TRH for TRH-R1. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Allosteric Modulation of the Dopamine Receptor by Conformationally Constrained Type VI β-Turn Peptidomimetics of Pro-Leu-Gly-NH₂
  作者：Ashish P. Vartak、Kevin Skoblenick、Nancy Thomas、Ram K. Mishra、Rodney L. Johnson

  DOI：10.1021/jm070895r

  日期：2007.12.27

  A peptidomimetic of Pro-Leu-Pro-NH2, 7, possessing an indolizidinone type VI beta-turn mimic was synthesized via improved high-yielding protocols for the preparation and Cbz protection of a-allylproline. Bicyclic peptidomimetic 7 and spirobicylic peptidomimetic 8 enhanced the binding of [H-3]N-propylnorapomorphine to dopamine receptors indicating that a type VI beta-turn is a possible bioactive conformation of the homochiral Pro-Leu-Pro-NH2 and Pro-Pro-Pro-NH2 analogues of Pro-Leu-Gly-NH2 at the dopamine receptor allosteric regulatory site.