dimethyl (2S,7S)-3,6-diaza-4,5-dioxo-2,7-diisobutyloctano-1,8-dicarboxylate | 147315-15-9

• 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: dimethyl (2S,7S)-3,6-diaza-4,5-dioxo-2,7-diisobutyloctano-1,8-dicarboxylate
• 英文别名: N,N'-oxalyl-bis-L-leucine methyl ester；MeO-Leu-CO-CO-Leu-OMe；methyl (2S)-2-[[2-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]amino]-2-oxoacetyl]amino]-4-methylpentanoate
• CAS: 147315-15-9
• 化学式: C₁₆H₂₈N₂O₆
• 分子量: 344.408
• InChiKey: IITJUVXJSBRZDK-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl (2S,7S)-3,6-diaza-4,5-dioxo-2,7-diisobutyloctano-1,8-dicarboxylate 在 sodium hydroxide 作用下， 反应 4.0h， 生成 bis-(S)-leucine oxalyl amide
  参考文献：
  名称：

  Oxalopeptides as core motifs for protein design

  摘要：

  草酰肽被证明是双向链延伸的有效核心结构，能够产生具有有趣折叠特性的肽同系物，因此构成了一种有用的蛋白质主链修饰策略。

  DOI：

  10.1039/c39930000092
• 作为产物：
  描述：

  L-亮氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 dimethyl (2S,7S)-3,6-diaza-4,5-dioxo-2,7-diisobutyloctano-1,8-dicarboxylate
  参考文献：
  名称：

  A simple synthesis of chiral macrocyclic tetraamides derived from α-amino acids

  摘要：

  Bisamidation of oxalyl chloride using four L-alpha-amino acid esters afforded chiral diesters which were reacted with three alpha,omega-diainines under high-pressure conditions (10 kbar) to give macrocyclic tetramides of C-2-symmetry. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00506-2

文献信息

• Chiral bis(amino alcohol)oxalamides as ligands for asymmetric catalysis. Ti(IV) catalyzed enantioselective addition of diethylzinc to aldehydes
  作者：Gonzalo Blay、Isabel Fernández、Alícia Marco-Aleixandre、José R. Pedro

  DOI：10.1016/j.tetasy.2005.01.039

  日期：2005.3

  Several chiral bis(aminoalcohol)oxalamides with C2-symmetry have been prepared and used as ligands for the enantioselective addition of diethylzinc to aromatic and aliphatic aldehydes. The reaction proceeds in the presence of titanium isopropoxide to give the corresponding (S)-alcohols with ee up to 78%. In the absence of Ti(IV), the alcohols with the opposite configuration are obtained.

  已经制备了几种具有C 2对称性的手性双（氨基醇）草酰胺，并用作将二乙基锌对映选择性加成到芳族和脂族醛上的配体。反应在异丙醇钛存在下进行，得到相应的（S）-醇，其ee高达78％。在没有Ti（IV）的情况下，获得具有相反构型的醇。
• Bis(Amino Acid) Oxalyl Amides as Ambidextrous Gelators of Water and Organic Solvents: Supramolecular Gels with Temperature Dependent Assembly/Dissolution Equilibrium
  作者：Janja Makarević、Milan Jokić、Berislav Perić、Vladislav Tomišić、Biserka Kojić-Prodić、Mladen Žinić

  DOI：10.1002/1521-3765(20010803)7:15<3328::aid-chem3328>3.0.co;2-c

  日期：2001.8.3

  bis(PhgOH) (5a) (Phg denotes (R)-phenylglycine) oxalyl amides are efficient low molecular weight organic gelators of various organic solvents and their mixtures as well as water, water/DMSO, and water/DMF mixtures. The organisational motifs in aqueous gels are dominated primarily by lipophilic interactions while those in organic solvents are formed by intermolecular hydrogen bonding. Most of the gels are thermoreversible

  双（LeuOH）（1a），双-（ValOH）（2a）和双（PhgOH）（5a）（Phg表示（R）-苯基甘氨酸）草酰酰胺是各种有机溶剂及其混合物的有效低分子量有机胶凝剂以及水，水/ DMSO和水/ DMF混合物。水性凝胶中的组织基序主要由亲脂性相互作用决定，而有机溶剂中的基序通过分子间氢键形成。大多数凝胶是热可逆的，并且可以稳定许多个月。然而，2a与有机溶剂形成不稳定的凝胶，该凝胶在老化后转变成各种晶体形状。对于某些1a /醇凝胶，发现醇介电常数（ε）和凝胶熔化温度（Tg）之间存在线性关系。所选凝胶的1 H NMR和FTIR光谱研究揭示了温度依赖性网络组装/溶解平衡的存在。在凝胶的1 H NMR光谱中，只能观察到溶解在截留溶剂中的分子。通过使用内标，可以确定溶解的胶凝剂分子的浓度。在FTIR光谱中，同时存在与网络组装和溶解的胶凝剂分子相对应的谱带。这样就可以通过两种方法确定Kgel值。从InKgel与1
• Supramolecular assembling using synthons with NH—CO(S)—CS—NH and NH—CO—CO—NH functionalities: crystal structures of (<i>S</i>,<i>S</i>)-<i>N</i>,<i>N</i>′-monothiooxalyldileucine methyl ester and its dithio analogue
  作者：Biserka Kojić-Prodić、Berislav Perić、Zoran Štefanić、Anton Meden、Janja Makarević、Milan Jokić、Mladen Žinić

  DOI：10.1107/s0108768103029173

  日期：2004.2.1

  To compare the structural properties of oxalamide and thiooxalamide groups in the formation of hydrogen bonds suitable for supramolecular assemblies a series of retropeptides was studied. Some of them, having oxalamide bridges, are gelators of organic solvents and water. However, retropeptides with oxygen replaced by the sp ² sulfur have not exhibited such properties. The crystal structures of the two title compounds are homostructural, i.e. they have similar packing arrangements. The monothio compound crystallizes in the orthorhombic space group P2₁2₁2₁ with two molecules in the asymmetric unit arranged in a hydrogen-bond network with an approximate 4₁ axis along the crystallographic b axis. However, the dithio and dioxo analogues crystallize in the tetragonal space group P4₁ with similar packing patterns and hydrogen-bonding systems arranged in agreement with a crystallographic 4₁ axis. Thus, these two analogues are isostructural having closely related hydrogen-bonding patterns in spite of the different size and polarity of oxygen and sulfur which serve as the proton acceptors.

  为了比较草酰胺基团和硫代草酰胺基团在形成适合超分子组装的氢键方面的结构特性，我们研究了一系列反肽。其中一些具有草酰胺桥的逆肽是有机溶剂和水的凝胶剂。然而，氧被 sp 2 硫所取代的逆肽却没有表现出这种特性。两种标题化合物的晶体结构是同结构的，即它们具有相似的堆积排列。一硫代化合物在正交空间群 P212121 中结晶，不对称单元中的两个分子排列成氢键网络，其近似的 41 轴沿晶体学 b 轴。然而，二硫代和二氧代类似物在四方空间群 P41 中结晶，具有类似的堆积模式和氢键系统，其排列与晶体学 41 轴一致。因此，尽管作为质子接受体的氧和硫的大小和极性不同，但这两种类似物结构相同，氢键模式密切相关。
• A simple synthesis of chiral macrocyclic tetraamides derived from α-amino acids
  作者：Tomasz Zieliński、Michał Achmatowicz、Janusz Jurczak

  DOI：10.1016/s0957-4166(02)00506-2

  日期：2002.9

  Bisamidation of oxalyl chloride using four L-alpha-amino acid esters afforded chiral diesters which were reacted with three alpha,omega-diainines under high-pressure conditions (10 kbar) to give macrocyclic tetramides of C-2-symmetry. (C) 2002 Published by Elsevier Science Ltd.
• Oxalopeptides as core motifs for protein design
  作者：Darshan Ranganathan、Narendra K. Vaish、Kavita Shah、Raja Roy、K. P. Madhusudanan

  DOI：10.1039/c39930000092

  日期：——

  Oxalopeptides are demonstrated to be useful core motifs for bi-directional chain elongation leading to peptide homologues with interesting folding behaviour, thus constituting a useful strategy for protein backbone modification.

  草酰肽被证明是双向链延伸的有效核心结构，能够产生具有有趣折叠特性的肽同系物，因此构成了一种有用的蛋白质主链修饰策略。