Boc-L-Phe-D-Oxd-OH | 1190398-80-1

• 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: Boc-L-Phe-D-Oxd-OH
• 英文别名: Boc-Phe-D-N(For(1))Thr(1)-OH；(4R,5S)-5-methyl-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]-2-oxo-1,3-oxazolidine-4-carboxylic acid
• CAS: 1190398-80-1
• 化学式: C₁₉H₂₄N₂O₇
• 分子量: 392.409
• InChiKey: ZDVRODPPAXIJBM-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-L-Phe-D-Oxd-OH 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.84h， 生成
  参考文献：
  名称：

  Formation of gels in the presence of metal ions

  摘要：

  A small library of stereoisomeric pseudopeptides able to make gels in different solvents has been prepared and their attitude to make gels in the presence of several metal ions was evaluated. Four benzyl esters and four carboxylic acids, all containing a moiety of azelaic acid (a long chain dicarboxylic acid) coupled with four different pseudopeptide moieties sharing the same skeleton (a phenyl group one atom apart from the oxazolidin-2-one carboxylic group), were synthesized in solution, by standard coupling reaction. The tendency of these pseudopeptides to form gels was evaluated using the inversion test of 10 mM solutions of pure compounds and of stoichiometric mixtures of pseudopeptides and metal ions. To obtain additional information on the molecular association, the gel samples were left dry in the air to form xerogels that were further analyzed using SEM and XRD. The formation of gel containing Zn(II) or Cu(II) ions gave good results in term of incorporation of the metal ions, while the presence of Cu(I), Al(III) and Mg(II) gave less satisfactory results. This outcome is a first insight in the formation of stable LMWGs formed by stoichiometric mixtures of pseudopeptides and metal ions. Further studies will be carried out to develop similar compounds of pharmacological interest.

  DOI：

  10.1007/s00726-011-0908-0
• 作为产物：
  描述：

  Boc-L-Phe-D-Oxd-OBn 在 10% palladium on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到Boc-L-Phe-D-Oxd-OH
  参考文献：
  名称：

  含有混合折叠体的恶唑烷二酮纳米纤维：合适的分子大小是多少？

  摘要：

  制备了一系列 Boc-( L -Phe- D - Oxd ) n- OBn (Boc= tert -butoxycarbonyl; Oxd=4-methyl-5-carboxy oxazolidin-2-one; Bn=benzyl) 类型的低聚物用于n =2-5。最短的低聚物，Boc-( L -Phe- D - Oxd ) 2-OBn，聚集并形成具有反平行β-折叠结构的纤维状材料，其中寡肽单元仅通过一个分子间氢键相互连接。较长的低聚物表现出结构异质性。它们通过在五聚体水平上形成分子内氢键开始组织成二级结构。低聚物的显微镜和衍射表明只有较短的低聚物具有结晶特征。

  DOI：

  10.1002/chem.200900185

文献信息

• Conformational Studies of Phe-Rich Foldamers by VCD Spectroscopy and ab Initio Calculations
  作者：Giovanna Longhi、Sergio Abbate、France Lebon、Nicola Castellucci、Piera Sabatino、Claudia Tomasini

  DOI：10.1021/jo300688n

  日期：2012.7.20

  Employing VCD spectroscopy, we demonstrate that the structural behavior of the oligomers Boc-(l-Phe-l-Oxd)n-OBn is similar from n = 2 to n = 6; ab initio calculations for the n = 1 case provide physical insight into the conformational properties. Further information is gained by IR, 1H NMR, and ECD spectroscopies. ECD spectra suggest the presence of different conformations between n = 1 on one side

  采用VCD光谱，我们证明了低聚物的Boc-的结构特性（升-Phe-升-Oxd）ñ -OBn是从类似Ñ = 2至Ñ = 6; n = 1情况的从头算起可提供对构象性质的物理洞察力。通过IR，1 H NMR和ECD光谱学获得了更多信息。ECD光谱表明，一侧的n = 1与另一侧的长链折叠子之间存在不同的构象。甲醇溶液中的VCD和吸收IR光谱可解释为PPII结构的指示。在的Boc-的情况下升-Phe-升-Oxd-OBN，在四氯化碳VCD光谱图4和详细的DFT计算分析使我们能够证明，人口最多的构象异构体显示的骨架二面角类似于PPII几何形状。这是一个了不起的结果，因为我们之前已经证明，Boc-（1- Ala- d- Oxd）n -OBn系列在β带状螺旋中折叠，该螺旋是3 10螺旋的一个亚型。
• Solid-State Properties and Vibrational Circular Dichroism Spectroscopy in Solution of Hybrid Foldamers Stereoisomeric Mixtures
  作者：Nicola Castellucci、Giuseppe Falini、Lorenzo Milli、Magda Monari、Sergio Abbate、Giovanna Longhi、Ettore Castiglioni、Giuseppe Mazzeo、Claudia Tomasini

  DOI：10.1002/cplu.201300306

  日期：2014.1

  Boc-(L-Phe-D-Oxd)2 -OBn (3). The preferred conformation of 1 ranges from a polyproline II (PPII) helix to β strands and we can gather that longer and more structured oligomers will form PPII helices. In contrast, compound 3 forms infinite antiparallel β-sheet structures; thus showing the strong effect of the reversal of the absolute configuration of the Oxd moieties on the secondary structure of these hybrid

  在缓慢蒸发Boc-（L-Phe-L-Oxd）2-OBn的1：1非对映异构混合物时（1; Boc =叔丁氧羰基; L-Oxd =反式-（4S，5R）-4-羧基5 -甲基恶唑烷丁-2-酮（Bn =苄氧羰基）和Boc-L-Phe-L-Oxd-D-Phe-L-Oxd-OBn（2）在甲基叔丁基醚中，适用于X射线衍射的单晶研究获得。相反，两种纯的低聚物在任何结晶条件下均导致形成无定形固体。在固相中充分阐明了两种低聚物的优先构象，并与Boc-（L-Phe-D-Oxd）2-OBn的已知构象进行了比较（3）。1的优选构象范围是从聚脯氨酸II（PPII）螺旋到β链，我们可以收集到更长，更结构化的低聚物将形成PPII螺旋​​。相反，化合物3形成无限的反平行β-折叠结构；因此显示出Oxd部分的绝对构型的逆转对这些杂合折叠子的二级结构的强烈影响。振动圆二色性分析表明，溶液中保留了相同的结果。最终，我们证明了1和2的
• A peptidic hydrogel that may behave as a “Trojan Horse”
  作者：Nicola Castellucci、Giorgio Sartor、Natalia Calonghi、Carola Parolin、Giuseppe Falini、Claudia Tomasini

  DOI：10.3762/bjoc.9.44

  日期：——

  A physical hydrogel prepared with the low-molecular-weight hydrogelator (LMWHG) CH₂(C₃H₆CO-L-Phe-D-Oxd-OH)₂ and water/ethanol mixture was applied as a potential “Trojan Horse” carrier into cells. By SEM and XRD analysis we could demonstrate that a fibrous structure is present in the xerogel, making a complex network. The gelator is derived from α-amino acids (Thr, Phe) and a fatty acid (azelaic acid) and is biocompatible: it was dosed to IGROV-1 cells, which internalized it, without significantly affecting the cell proliferation. To check the internalization process by confocal microscopy, fluorescent hydrogels were prepared, introducing the fluorescent dansyl moiety into the mixture.

  用低分子量水凝胶剂（LMWHG）CH2（C3H6CO-L-Phe-D-Oxd-OH）2和水/乙醇混合物制备的物理水凝胶被应用为潜在的“特洛伊木马”载体进入细胞。通过扫描电镜和X射线衍射分析，我们可以证明干凝胶中存在纤维结构，形成复杂的网络。该凝胶剂来源于α-氨基酸（苏氨酸，苯丙氨酸）和脂肪酸（癸二酸）并且具有生物相容性：它被用于IGROV-1细胞，细胞内摄取，而不显著影响细胞增殖。为了通过共聚焦显微镜检查内摄过程，制备了荧光水凝胶，将荧光丹磺酰基引入混合物中。
• Pseudopeptides Designed to Form Supramolecular Helixes: The Role of the Stereogenic Centers
  作者：Gaetano Angelici、Nicola Castellucci、Giuseppe Falini、Daniel Huster、Magda Monari、Claudia Tomasini

  DOI：10.1021/cg9012558

  日期：2010.2.3

  The two epimers Boc-L-Phe-D-Oxd-(S)-beta(3)-hPhg-OBn (1) and Boc-L-Phe-D-Oxd-(R)-beta(3)-hPhg-OBn (2) have been prepared by standard methods in solution, and their conformation was analyzed both in solution and in the solid state. While in solution 1 shows it random coil structure, 2 tends to assume a gamma-turn conformation that is nearly retained in the solid state. On the other hand, in the solid state molecules of 1 associate generating it helix that involves the formation of elongated crystals with hexagonal cross-section. This effect is not observed in the crystals formed by Boc-L-Phe-D-Oxd-(R)-beta(3)-hPhg-OBn 2.