Fc[CO-L-Gly-OMe]2 | 866958-35-2

• 英文名称: Fc[CO-L-Gly-OMe]2
• 英文别名: Fc[CO-L-Gly-OMe]₂；Fe[C5H4-CO-Gly-OMe]2；1,n'-Fc(CONHCH2COOMe)2；1,n'-Fc(CO-Gly-OMe)2
• CAS: 866958-35-2
• 化学式: C₁₈H₂₀FeN₂O₆
• 分子量: 416.214
• InChiKey: LZVPLPQOKCWNCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  Fc[CO-L-Gly-OMe]2 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以64 %的产率得到1,1'-Fc(CO-Gly-OH)2
  参考文献：
  名称：

  Synthesis of Chiral Macrocycles Based on Bispidine

  摘要：

  DOI：

  10.1134/s1070428023030090
• 作为产物：
  描述：

  1,1'-ferrocenyldicarbonyl chloride 、 甘氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88 %的产率得到Fc[CO-L-Gly-OMe]2
  参考文献：
  名称：

  Synthesis of Chiral Macrocycles Based on Bispidine

  摘要：

  DOI：

  10.1134/s1070428023030090

文献信息

• Synthesis and characterization of new ferrocene peptide conjugates
  作者：Cailin Drexler、Mark Milne、Erin Morgan、Michael Jennings、H.-B. Kraatz

  DOI：10.1039/b817670a

  日期：——

  (Fc)-conjugates were prepared and their properties were investigates in solution and the solid state: (a) acyclic diamine-linked 1,n'-Fc conjugates, (b) acyclic diamine-linked 1,n'-Fc peptide conjugates, and (c) cyclic 1,n'-Fc-peptide diamine conjugates. In all cases, the synthetic procedure started from 1,1'-ferrocenecarboxylic acid methyl ester or 1,1'-ferrocene dicarboxylic acid or their amino acid conjugates

  制备了三类二胺连接的二茂铁（Fc）-共轭物，并在溶液和固态下研究了它们的性质：（a）无环二胺连接的1，n'-Fc共轭物，（b）无环二胺连接的1，n '-Fc肽缀合物和（c）环状1，n'-Fc-肽二胺缀合物。在所有情况下，合成方法均始于1,1'-二茂铁羧酸甲酯或1,1'-二茂铁二羧酸或其氨基酸缀合物，然后与二氨基烷烃偶联。所得的缀合物表现出H键，如通过温度和在某些情况下浓度依赖性的NMR位移以及其中一种缀合物的固态结构所证明的。我们的研究表明，Fc-二胺连接系统的结构特性与相关的胱胺结合物不同，
• Unsymmetrical 1,n′-disubstituted ferrocenoyl peptides: convenient one pot synthesis and solution structures by CD and NMR spectroscopy
  作者：Srećko I. Kirin、Dirk Wissenbach、Nils Metzler-Nolte

  DOI：10.1039/b504187b

  日期：——

  disubstituted derivatives 1–4 and 6. CD spectra were recorded for all derivatives in CH2Cl2. They clearly show a P helical isomer of the ferrocene moiety for the L amino acid derivatives 1–3 and M helicity for the DPhe derivative 1a. The racemic derivative 6 shows only intermolecular interactions, while the Pro derivative 5, which is devoid of amide protons, most likely exists in an “open conformation”. Most

  我们对不对称进行系统研究 氨基酸 1,1'-二茂铁的衍生物 二羧酸。提出了一种方便，通用的一锅法合成方法，其中不对称氨基酸 衍生物很容易被 柱层析。以下二茂铁Fe [C 5 H 4 -CO-Aaa 1 -OMe] [C 5 H 4 -CO-Aaa 2 -OMe]氨基酸 制备并通过以下方法研究其溶液结构 核磁共振和CD光谱分析（Aaa 1 = Aaa 2 = Phe，1 ; Aaa 1 = Aaa 2 = D Phe，1a ; Aaa 1 = Aaa 2 =翼，2 ; Aaa 1 = Phe，Aaa 2 =翼，3 ; Aaa 1 = D Phe，Aaa 2 = Ala，4；Aaa 1 = Aaa 2 = Pro，5 ; Aaa 1 = Aaa 2 = Gly，6 ; 全部氨基酸除非另有说明，否则均为纯L对映体）。核磁共振波谱 在 CDCl 3确认分子内的二取代衍生物氢键1 - 4和6。CD光谱记录了CH
• Ferrocene–Tryptophan Conjugate: An Example of a Redox-Controlled Reversible Supramolecular Nanofiber Network
  作者：Bimalendu Adhikari、Rouzbeh Afrasiabi、Heinz-Bernhard Kraatz

  DOI：10.1021/om4004779

  日期：2013.10.28

  In this study, the tryptophan derivative of ferrocene-1,1'-dicarboxylic acid self-assembles in toluene to form a supramolecular nanofibrillar network structure. The ferrocene bioconjugate based nanofibers are responsive toward oxidation/reduction and show thermo and redox reversibility. Interestingly, redox-induced reversible morphological transformations between nanofiber and spheroid were observed. The self-assembly was characterized by NMR spectroscopy, FT-IR spectroscopy, UV-vis spectroscopy, circular dichroism (CD), and transmission electron microscopy (TEM).
• A systematic evaluation of different hydrogen bonding patterns in unsymmetrical 1,n′-disubstituted ferrocenoyl peptides
  作者：Srećko I. Kirin、Ulrich Schatzschneider、S. David Köster、Daniel Siebler、Nils Metzler-Nolte

  DOI：10.1016/j.ica.2008.01.050

  日期：2009.2

  The synthesis and spectroscopic characterization of 21 1,1'-disubstituted ferrocenoyl peptides of the general formula [Fe(C5H4-CO-Aa1-OR) (C5H4-CO-Aa2-OR')] is reported, with Aa1 and Aa2 being different amino acids. The one-pot synthesis from activated ferrocene-1,1'-dicarboxylic acid and two different amino acid esters gives the unsymmetrical ferrocenoyl peptides in yields between 27% and 42%, which can be easily separated from their symmetrical byproducts by column chromatography. All new compounds are comprehensively characterized by mass spectrometry (El and FAB, including high-resolution EI-MS), H-1 and C-13 NMR, and UV/Vis spectroscopy. CD spectroscopy in conjunction with H-1 NMR is used to elucidate the solution structures. Using the achiral glycine (Gly) as Aa1 permits to determine qualitatively the structure-determining influence of the different amino acids Aa2. Helically chiral structures in ferrocene amino acids in this study are stabilized by hydrogen bonds. If one hydrogen bond partner is systematically moved away by the introduction of methylene groups, then indeed the strength of the hydrogen bond decreases as indicated by 1 H NMR chemical shifts of the amide protons and the strength of characteristic CD bands. As proline (Pro) is the only naturally accuring secondary amino acid it cannot contribute any amide proton to intra-strand hydrogen bonding. DFT calculations on the compound [Fe(C5H4-CO-GlyOMe)(C5H4-CO-Pro-OMe)] with one achiral and one secondary amino acid were therefore performed to quantify the more subtle influence of the relative orientations of the ferrocene carbonyl groups and the cis-/trans-conformation of both amide bonds. Not unexpectedly, the conformations with both amide bonds in cis orientation are highest in energy. Surprisingly, the calculations suggest the presence of a low-energy conformation with a non-classical hydrogen bond between the proline ester carbonyl oxygen and a glycine Ha atom. However, a second conformation with no apparent intra-strand contacts but optimal positioning of all relevant groups is similar in energy. Although two conformations were observed in solution for this compound, the experimental data did not permit to assign those two conformations. (C) 2008 Elsevier B. V. All rights reserved.