Fc-Gly-OMe | 230951-81-2

• 英文名称: Fc-Gly-OMe
• 英文别名: N-ferrocenoyl glycine methyl ester；N-ferrocenoylglycine methyl ether
• CAS: 230951-81-2
• 化学式: C₁₄H₁₅FeNO₃
• 分子量: 301.125
• InChiKey: MWKJKDOLBYSEAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  Fc-Gly-OMe 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 Fc-Gly-OH
  参考文献：
  名称：

  1-二茂铁氨基酸超分子手性的起源

  摘要：

  π-共轭氨基酸广泛应用于手性材料中，其中手性活性被认为源于超分子堆积。然而，分子内的贡献在很大程度上被忽略了。在这项工作中，我们报告二茂铁共轭氨基酸的分子内手性转移行为取决于取代基，这影响多个分子内相互作用的模式以及分子几何形状。这项工作揭示了手性和手性活动的结构基础和结构-性质关系。基于单晶结构和密度泛函理论计算，我们证明了分子内弱力，包括氢键、CH⋯π相互作用和范德华相互作用，影响分子几何形状并促成不同的棉花效应。这项工作为自组装系统中被忽略的分子内因素提供了证据，并为功能性手性光学系统的制造铺平了道路。

  DOI：

  10.1039/d1dt01905h
• 作为产物：
  描述：

  ferrocenoyl hydroxybenzotriazole ester 、 甘胺酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Fc-Gly-OMe
  参考文献：
  名称：

  Ferrocene tripeptide Gly-Pro-Arg conjugates: Synthesis and inhibitory effects on Alzheimer’s Aβ1–42 fibrillogenesis and Aβ-induced cytotoxicity in vitro

  摘要：

  Alzheimer's disease (AD) is the most common cause of dementia, and currently there is no clinical treatment to cure it or to halt its progression. Aggregation and fibril formation of beta-amyloid peptides (A beta) are central events in the pathogenesis of AD. Many efforts have been spent on the development of effective inhibitors to prevent A beta fibrillogenesis and cause disaggregation of preformed A beta fibrils. In this study, the conjugates of ferrocene and Gly-Pro-Arg (GPR) tripeptide, Boc-Gly-Pro-Arg(NO2)-Fca-OMe (4, GPR-Fca) and Fc-Gly-Pro-Arg-OMe (7, Fc-GPR) (Fc: ferrocene; Fca: ferrocene amino acid) were synthesized by HOBT/HBTU protocol in solution. These ferrocene GPR conjugates were employed to inhibit A beta(1-42) fibrillogenesis and to disaggregate preformed A beta fibrils. The inhibitory properties of ferrocene GPR conjugates on A beta(1-42) fibrillogenesis were evaluated by thioflavin T (ThT) fluorescence assay, and confirmed by atomic force microscopy (AFM) analysis. The interaction between the ferrocene GPR conjugates and A beta(1-42) was monitored by electrochemical means. Our results showed that both GPR and GPR-Fca can significantly inhibit the fibril formation of A beta(1-42), and cause disaggregation of the preformed fibrils. As expected, GPR-Fca shows stronger inhibitory effect on A beta(1-42) fibrillogenesis than that of its parent peptide GPR. In contrast, Fc-GPR shows no inhibitory effect on fibrillogenesis of A beta(1-42). Furthermore, GPR-Fca demonstrates significantly protection against A beta-induced cytotoxicity and exhibits high resistance to proteolysis and good lipophilicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.030

文献信息

• Synthesis and structural characterisation of redox-responsive N-ferrocenoyl amino acid esters; the X-ray crystal structure of N-ferrocenoyl alanine methyl ester; electrochemical anion recognition and 1H NMR complexation studies
  作者：Michael J Sheehy、John F Gallagher、Mashita Yamashita、Yoshiteru Ida、Jennifer White-Colangelo、Jeremi Johnson、Ron Orlando、Peter T.M Kenny

  DOI：10.1016/j.jorganchem.2004.02.001

  日期：2004.5

  N-ferrocenoyl-l-alanine methyl ester 4 has been determined and contains two molecules which differ slightly in conformation in the asymmetric unit of space group P21 (No. 4); principal dimensions are amide N(H)CO 1.224(6) and 1.231(6) Å, ester CO 1.220(10) and 1.190(7) Å, with N–H⋯OC(amide) as the primary intermolecular hydrogen bond, N⋯O 2.992(6) and 2.971(6) Å and with graph set C(4).

  所述Ñ -ferrocenoyl氨基酸酯衍生物FcCOR FC =（η 5 -C 5 H ^ 5）的Fe（η 5 -C 5 H ^ 4）}，其中R =甘氨酸（OME）1，甘氨酸（OET）2，甘氨酸（OBN ）3，l-Ala（OMe）4，l-Ala（OEt）5，l-Leu（OMe）6，l-Leu（OEt）7，l-Leu（OBn）8，l-Phe（OMe）9和l-Phe（OEt）10通过使用1，3-二环己基碳二亚胺（DCC），1-羟基苯并三唑（HOBt）方案将二茂铁羧酸与合适的氨基酸酯原料偶联来制备二价铁，并已通过光谱技术对其进行了表征。化合物的电化学感测阴离子行为1 - 10与使用铂微盘工作电极几个阴离子被描述，连同1个1 H NMR阴离子络合研究。N-二茂铁基-1-丙氨酸甲酯4的X射线单晶结构已经确定，并且包含两个分子，在空间群P2 1的不对称单元中构象略有不同（第4号）；主要尺寸为酰胺N（H）C
• Synthesis of ferrocenoyl amino acid derivatives via homogeneous catalytic aminocarbonylation
  作者：Árpád Kuik、Rita Skoda-Földes、János Balogh、László Kollár

  DOI：10.1016/j.jorganchem.2005.03.054

  日期：2005.7