N,N'-bis(N-Cbz-L-phenylalanyl)-1,2-diaminoethane | 157756-00-8

• 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: N,N'-bis(N-Cbz-L-phenylalanyl)-1,2-diaminoethane
• 英文别名: benzyl N-[(2S)-1-oxo-3-phenyl-1-[2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]ethylamino]propan-2-yl]carbamate
• CAS: 157756-00-8
• 化学式: C₃₆H₃₈N₄O₆
• 分子量: 622.721
• InChiKey: BHNLNUXDNMJNCL-ACHIHNKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(N-Cbz-L-phenylalanyl)-1,2-diaminoethane 在 氢溴酸 、 溶剂黄146 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 1,2-ethano-bis(L-Phe)
  参考文献：
  名称：

  A simple peptidomimetic that self-associates on the solid state to form a nanoporous architecture containing chiral π-channels

  摘要：

  源自苯丙氨酸的简单拟肽化合物晶体结构显示，形成了包含一维π通道的纳米多孔结构，其中芳香环作为手性通道壁的唯一组分。

  DOI：

  10.1039/b922172g
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 27.0h， 生成 N,N'-bis(N-Cbz-L-phenylalanyl)-1,2-diaminoethane
  参考文献：
  名称：

  U-Turn 预组织肽模拟物的有效大环化：分子内氢键和疏溶剂效应的作用

  摘要：

  源自氨基酸的简单拟肽分子在乙腈中与间位和对位双（溴甲基）苯反应，非常有效地产生大环结构。环化反应不需要高稀释技术，并且似乎对形成的大环的大小不敏感。通过 (1)H NMR、单晶 X 射线衍射、荧光测量和分子力学获得的数据分析表明，折叠构象可以预先组织系统以实现有效的环化。分析了在折叠构象存在下分子内氢键和疏溶剂效应所起的作用。

  DOI：

  10.1021/ja0284759

文献信息

• Photochemistry of dipeptides in aqueous solution
  作者：Roger R. Hill、John D. Coyle、David Birch、Edwin Dawe、Graham E. Jeffs、David Randall、Iwan Stec、Tessa M. Stevenson

  DOI：10.1021/ja00005a053

  日期：1991.2

  The photochemical lability of peptides is poorly understood, largely because of the lack of product data. In the present study, product analyses have been carried out following the photolyses in aqueous solution of selected glycyl dipeptides (Gly-Gly, DL-AIa-GIy, L-VaI-GIy, L-Pro-Gly, L-Phe-Gly, and Gly-L-Phe), L-prolyl-L-phenylalanine, and L-phenylalanyl-L-proline. Efficient deamination and decarboxylation

  人们对肽的光化学不稳定性知之甚少，主要是因为缺乏产品数据。在本研究中，在选定的甘氨酰二肽（Gly-Gly、DL-Ala-Gly、L-Val-Gly、L-Pro-Gly、L-Phe-Gly、和 Gly-L-Phe)、L-脯氨酰-L-苯丙氨酸和 L-苯丙氨酰-L-脯氨酸。脂肪族二肽的有效脱氨基和脱羧在涉及肽键的光诱导电子转移过程中产生简单酰胺的热前体。苯丙氨酰肽光降解的类似途径受到其他类型反应的竞争。
• Chiral Diaminodiamide Copper(II) Complexes for the Enantioselective Recognition of Amino Acids: Synthesis of the Ligands and Formation Constants
  作者：Elisabetta Armani、Rosangela Marchelli、Arnaldo Dossena、Giuseppe Casnati、Francesco Dallavalle

  DOI：10.1002/hlca.19860690818

  日期：1986.12.10

  -bis(aminoacyl)propanediamines (AA-NN-2 and AA-NN-3, respectively, AA = alanine, phenylalanine, valine) were synthesized as the dihydrochlorides, and their complexes with Cu(II) studied potentiometrically. Since these ligands in the presence of Cu(II) are able to perform chiral resolution of D,L-dansylamino acids in HPLC (reversed phase), in a certain pH range (6.5–8.5), it is important to know the equilibria existing

  （S，S）-N，N'-双（氨基酰基）乙烷-和（S，S）-N，N'-双（氨基酰基）丙烷二胺（分别为AA-NN-2和AA-NN-3 =丙氨酸，苯丙氨酸，缬氨酸）合成为二盐酸盐，并用电位法研究了它们与Cu（II）的配合物。由于这些配体在Cu（II）存在下能够在一定pH范围（6.5-8.5）中在HPLC（反相）中进行D，L-丹酰氨基酸的手性拆分，因此重要的是要知道存在的平衡在水溶液中的配体和铜之间。对于AA-NN-2，有四种，CuLH 3+，CuL 2 +，Cu 2检测到L 2 H和CuLH -2，而对于AA-NN-3，仅发现CuLH 3+，CuL 2+和CuLH -2。目的是找出识别过程中可能涉及哪些复合体。
• Copper(<scp>ii</scp>) complexes of macrocyclic and open-chain pseudopeptidic ligands: synthesis, characterization and interaction with dicarboxylates
  作者：Enrico Faggi、Raquel Gavara、Michael Bolte、Lluís Fajarí、Luís Juliá、Laura Rodríguez、Ignacio Alfonso

  DOI：10.1039/c5dt01496d

  日期：——

  dinuclear Cu(II) complexes were prepared with pseudopeptidic open chain and macrocyclic ligands, respectively. They were characterized by UV-vis spectroscopy, EPR, HRMS and X-ray diffraction. The Cu(II) cation is coordinated by two amines and two deprotonated amides, in a slightly distorted square planar coordination geometry. The complexes interact with several substituted dicarboxylates, as shown by

  单核和双核Cu（II）配合物分别用假肽开链和大环配体制备。通过紫外可见光谱，EPR，HRMS和X射线衍射对它们进行了表征。Cu（II）阳离子由两种胺和两种去质子化的酰胺配位，呈稍微扭曲的正方形平面配位几何形状。如UV-vis滴定法和EPR实验所示，络合物与几种取代的二羧酸酯相互作用。单核和双核复合物与非常相似的具有生物学意义的二羧酸盐（苹果酸和天冬氨酸）的相互作用产生了截然不同的结果：在第一种情况下，几乎定量地获得了三元复合物[配体-金属-二羧酸]。铜（II）位移形成Cu（Asp）2是主要的。
• A simple, safe and robust system for hydrogenation “without high-pressure gases” under batch and flow conditions using a liquid organic hydrogen carrier
  作者：Raul Porcar、Andrés Mollar-Cuni、David Ventura-Espinosa、Santiago V. Luis、Eduardo García-Verdugo、Jose A. Mata

  DOI：10.1039/d1gc03850h

  日期：——

  generation of hydrogen under mild conditions is reported. A device formed by a packed bed reactor containing a ruthenium N-heterocyclic carbene complex [Ru(arene)(Cl)2(NHC)] supported onto graphene (NHC-Ru-rGO) and a liquid–gas separator allows the continuous generation of hydrogen produced by the dehydrogenative coupling of silanes and alcohols under mild and safe conditions. The highly pure hydrogen generated

  报道了一种简单、安全和稳健的系统，用于在温和条件下连续、原位和按需产生氢气。一种由填充床反应器形成的装置，该反应器包含负载在石墨烯 ( NHC-Ru-rGO ) 上的钌 N-杂环卡宾配合物 [Ru(arene)(Cl) 2 (NHC)]和液-气分离器，可以连续生成硅烷和醇在温和安全条件下脱氢偶联产生的氢气。产生的高纯度氢气可用于间歇和连续流动条件下的进一步氢化反应。
• Chiral bis(amino amides) as chiral solvating agents for enantiomeric excess determination of α-hydroxy and arylpropionic acids
  作者：Belén Altava、M. Isabel Burguete、Noèlia Carbó、Jorge Escorihuela、Santiago V. Luis

  DOI：10.1016/j.tetasy.2010.05.010

  日期：2010.4

  A family of bis(amino amides) derived from natural amino acids has been synthesized and tested for the NMR enantiodiscrimination, as chiral solvating agents, for enantiomeric excess determination of some carboxylic acids. Those bis(amino amide) receptors contain different structural modifications and the splitting of the signals of the acids, after addition of the corresponding CSAs, depends on those structural variables. The influence of aminoacid side chain and the nature of the aliphatic spacer are important parameters to obtain good chiral discriminations. The results obtained clearly show the chiral recognition abilities of these bis(amino amide) ligands and suggest their advantageous use as chiral solvating agents for carboxylic acids. The binding between bis(amino amides) and carboxylic acids has been studied by ESI-MS, NMR, DSC, and molecular modeling. The data suggest that enantiodiscrimination involves the formation of an ionic pair after proton transfer from the carboxylic substrate to the bis(amino amides). (C) 2010 Elsevier Ltd. All rights reserved.