Boc-L-Ala-D-Phe-OMe

• 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-Ala-D-Phe-OMe
• 英文别名: methyl (2R)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-phenylpropanoate
• 化学式: C₁₈H₂₆N₂O₅
• 分子量: 350.415
• InChiKey: OPQNQLXQVYFUHB-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Boc-L-Ala-D-Phe-OMe 在 甲酸 作用下， 以 甲苯 、 仲丁醇 为溶剂， 反应 2.0h， 生成 环(丙氨酸-苯丙氨酸)二肽
  参考文献：
  名称：

  Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides

  摘要：

  The capacity factors, k', of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k' values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k'LL is larger than k'LD, and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k'LL is smaller than k'DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k' values of larger peptides and the hydrophobicity and related properties of peptides.

  DOI：

  10.1021/ac00062a010
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 D-苯丙氨酸甲酯 在 硼酸三(2,2,2-三氟乙基)酯 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以42%的产率得到Boc-L-Ala-D-Phe-OMe
  参考文献：
  名称：

  使用 B(OCH2CF3)3 从羧酸和胺直接合成酰胺

  摘要：

  B(OCH 2 CF 3 ) 3由易得的B 2 O 3和2,2,2-三氟乙醇制备，是一种有效的试剂，可用于多种羧酸与多种胺的直接酰胺化。在大多数情况下，可以使用市售树脂通过简单的过滤程序纯化酰胺产物，无需进行水处理或色谱法。N-保护的氨基酸与伯胺和仲胺的酰胺化有效进行，外消旋化水平非常低。B(OCH 2 CF 3 ) 3 通过二甲基甲酰胺的转酰胺基作用，也可用于一系列胺的甲酰化反应，收率良好至极好。

  DOI：

  10.1021/jo400509n

文献信息

• Effect of Stereochemistry on Chirality and Gelation Properties of Supramolecular Self‐Assemblies
  作者：Minggao Qin、Yaqian Zhang、Chao Xing、Li Yang、Changli Zhao、Xiaoqiu Dou、Chuanliang Feng

  DOI：10.1002/chem.202004533

  日期：2021.2.10

  by the amino acid adjacent to the benzene core, irrespective of the absolute configuration of the C‐terminal amino acid. In addition, molecular chirality also has a significant influence on the gelation behavior. For the diphenylalanine‐based gelators, the homochiral gelators can be gelled through a conventional heating–cooling process, whereas heterochiral gelators form translucent stable gels under

  尽管已经在各种结构水平上制备了手性纳米结构，但是手性从分子到超分子自组装的转移和扩增仍然令人费解，特别是对于杂手性分子而言。在此，C 2的四个系列设计并合成了具有各种氨基酸序列和不同手性的基于对称二肽的衍生物。实现了分子手性向超分子组装体的转录和扩增。结果表明，超分子手性仅由与苯核心相邻的氨基酸决定，而与C端氨基酸的绝对构型无关。另外，分子手性也对胶凝行为具有重要影响。对于基于二苯丙氨酸的胶凝剂，同手性胶凝剂可以通过常规的加热-冷却过程进行胶凝，而异手性胶凝剂在超声处理下形成半透明的稳定凝胶。外消旋凝胶比纯对映异构体具有更高的机械性能。
• Direct Synthesis of Amides from Carboxylic Acids and Amines Using B(OCH₂CF₃)₃
  作者：Rachel M. Lanigan、Pavel Starkov、Tom D. Sheppard

  DOI：10.1021/jo400509n

  日期：2013.5.3

  range of amines. In most cases, the amide products can be purified by a simple filtration procedure using commercially available resins, with no need for aqueous workup or chromatography. The amidation of N-protected amino acids with both primary and secondary amines proceeds effectively, with very low levels of racemization. B(OCH2CF3)3 can also be used for the formylation of a range of amines in good

  B(OCH 2 CF 3 ) 3由易得的B 2 O 3和2,2,2-三氟乙醇制备，是一种有效的试剂，可用于多种羧酸与多种胺的直接酰胺化。在大多数情况下，可以使用市售树脂通过简单的过滤程序纯化酰胺产物，无需进行水处理或色谱法。N-保护的氨基酸与伯胺和仲胺的酰胺化有效进行，外消旋化水平非常低。B(OCH 2 CF 3 ) 3 通过二甲基甲酰胺的转酰胺基作用，也可用于一系列胺的甲酰化反应，收率良好至极好。
• Chiral Overpass Induction in Dynamic Helical Polymers Bearing Pendant Groups with Two Chiral Centers
  作者：Esteban Suárez‐Picado、Emilio Quiñoá、Ricardo Riguera、Félix Freire

  DOI：10.1002/anie.201915213

  日期：2020.3.9

  thereby cancelling the order from the first chiral moiety. This result was achieved through proper coordination with a metal cation. As proof of concept, poly(phenylacetylene)s (PPAs) that bear one and two chiral amino acid units of different sizes and configuration combinations (l/d-alanine and l/d-phenylalanine) as pendants were evaluated. In total, ten polymers were studied. This constitutes the first

  研究了带有两个手性中心的侧基的螺旋聚合物的动力学行为。靠近或远离主链的手性单元的受控构象变化促进了不同的螺旋结构。尽管第一个残基通常负责确定特定的螺旋度（P或M），但我们现在发现，第二个手性中心在空间上更靠近主链时，也能够诱导出较好的螺旋感，从而消除了从第一个手性部分的顺序。该结果是通过与金属阳离子的适当配位而实现的。作为概念证明，评估了带有一个和两个不同大小和构型组合（l / d-丙氨酸和l / d-苯丙氨酸）的手性氨基酸单元的聚苯乙炔（PPA）作为侧基。总共，研究了十种聚合物。这是第一个从遥远的立体中心对带有复杂手性悬垂物的聚合物进行轴向控制的报道。
• Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides
  作者：Noriaki. Funasaki、Sakae. Hada、Saburo. Neya

  DOI：10.1021/ac00062a010

  日期：1993.7.15

  The capacity factors, k', of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k' values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k'LL is larger than k'LD, and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k'LL is smaller than k'DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k' values of larger peptides and the hydrophobicity and related properties of peptides.