cyclo-(D-Ala-L-Ala) | 35590-65-9

• 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: cyclo-(D-Ala-L-Ala)
• 英文别名: (3R,6S)-3,6-dimethylpiperazine-2,5-dione
• CAS: 35590-65-9
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: WWISPHBAYBECQZ-ZXZARUISSA-N

物化性质

• 熔点：
  291 °C
• 沸点：
  453.0±38.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclo-(D-Ala-L-Ala) 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2,5-dimethyl-piperazine
  参考文献：
  名称：

  WO2024054901A1

  摘要：

  公开号：
• 作为产物：
  描述：

  Boc-Ala-Ala-O-pentachlorphenylester 在 sodium ethanolate 、 三氟乙酸 、 N,N-二乙基苯胺 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 2.5h， 生成 cyclo-(D-Ala-L-Ala)
  参考文献：
  名称：

  15N NMR spectroscopy. 19—spectroscopic characterization of cyclodipeptides (2,5-dioxopiperazines)

  摘要：

  AbstractVarious cyclodipeptides containing glycine, alanine, leucine, valine, phenylalanine, phenylglycine and sarcosine units were synthesized by cyclization of dipeptide pentachlorophenyl esters. The 13C and natural abundance 15N NMR spectra of these heterocycles were measured in trifluoroacetic acid and compared with the spectra of the corresponding amino acids and polypeptides. The 13C NMR carbonyl signals of all cyclodipeptides show a 1.5–4.0 ppm upfield shift relative to the corresponding polypeptides. The 15N NMR signals show no such consistent relationship. The substituent effects and the neighbouring residue effects observed in the 15N NMR spectra of the cyclodipeptides are different from those of polypeptides, while the one bond NH coupling constant of cis and trans amide groups was almost identical. The nitrogen and the carbonyl signal of the Gly units in cyclo‐Gly‐Phe show an extraordinary downfield shift, reflecting the interaction of the phenyl group with the 2,5‐dioxopiperazine ring.

  DOI：

  10.1002/mrc.1270130111

文献信息

• Epimerization of Cyclic Alanyl-Alanine in Basic Solutions
  作者：Toratane Munegumi、Takeshi Fujimoto、Michio Takada、Nozomi Nagashima

  DOI：10.13005/ojc/300103

  日期：2014.3.30

  Alanine anhydrides (Cyclo-(Ala-Ala)) are the simplest dipeptides that have two chiral centers and three diastereomers: Cyclo-(L-Ala-L-Ala), Cyclo-(D-Ala-D-Ala), and Cyclo-(L-Ala-D-Ala).Analysis of the epimerization of these peptides may throw light on the development of homochirality in proteins. We show that the epimerization rate of Cyclo-(L-Ala-L-Ala) and Cyclo-(D-Ala-D-Ala) is higher than that of Cyclo-(L-Ala-D-Ala), while the ring-opening rates of Cyclo-(L-Ala-L-Ala) and Cyclo-(D-Ala-D-Ala) arelower than that of Cyclo-(L-Ala-D-Ala) in basic aqueous solutions. The total reaction resulted in the preferred stability of Cyclo-(L-Ala-L-Ala) and Cyclo-(D-Ala-D-Ala) to Cyclo-(D-Ala-L-Ala).

  丙氨酸酐（环-(丙-丙)）是最简单的二肽，具有两个手性中心和三种非对映异构体：环-(L-丙-L-丙)、环-(D-丙-D-丙)和环-(L-丙-D-丙)。分析这些肽的差向异构化可能有助于揭示蛋白质中同手性的发展。我们表明，环-(L-丙-L-丙)和环-(D-丙-D-丙)的差向异构化速率高于环-(L-丙-D-丙)，而在碱性水溶液中，环-(L-丙-L-丙)和环-(D-丙-D-丙)的环开裂速率低于环-(L-丙-D-丙)。总反应导致了环-(L-丙-L-丙)和环-(D-丙-D-丙)相对于环-(D-丙-L-丙)的优先稳定性。
• Facile Synthesis of Cyclic Dipeptides and Detection of Racemization
  作者：Toshihisa Ueda、Morinobu Saito、Tetsuo Kato、Nobuo Izumiya

  DOI：10.1246/bcsj.56.568

  日期：1983.2

  Several cyclic dipeptides were synthesized by refluxing methanolic solution of dipeptide methyl esters in high yield and purity. Cyclic dipeptides prepared by the Fischer method, the Nitecki method, and the present methanol-reflux method were compared with respect to yield and optical purity. The methanol-reflux method usually gave good results. High-performance liquid chromatography was effectively applied to detect racemization.

  通过回流二肽甲酯的甲醇溶液，合成了几个高产率和高纯度的环状二肽。通过Fischer法、Nitecki法和当前的甲醇回流法准备的环状二肽，在产率和光学纯度方面进行了比较。甲醇回流法通常能得到良好的结果。高效液相色谱法有效地应用于检测外消旋化。
• Efficient Transformation of Azides to Primary Amines Using the Mild and Easily Accessible CeCl₃·7H₂O/NaI System
  作者：Giuseppe Bartoli、Giustino Di Antonio、Riccardo Giovannini、Sandra Giuli、Silvia Lanari、Melissa Paoletti、Enrico Marcantoni

  DOI：10.1021/jo7024288

  日期：2008.3.1

  have highlighted the capability of NaI as a useful reagent for this transformation when it is used in combination with a Lewis acid promoter. However, these methods often suffer from harsh reaction conditions; for this reason, the development of a simple and efficient protocol using NaI in presence of inexpensive and readily available cerium salts Lewis acids would extend the scope of this organic transformation

  由于氮的功能，叠氮基在胺的合成中起重要作用，并且报道了许多将叠氮化物还原为伯胺的方法。最近的报道强调了当与路易斯酸促进剂结合使用时，NaI作为用于这种转化的有用试剂的能力。然而，这些方法经常遭受苛刻的反应条件。由于这个原因，在廉价和易于获得的铈盐路易斯酸存在下使用NaI的简单有效的方法的开发将扩展这种有机转化的范围。为了继续关注CeCl 3 ·7H 2 O / NaI系统的使用，在本文中，我们报告了存在CeCl 3时叠氮化物如何被NaI还原·在中性条件下，在回流的乙腈中·7H 2 O生成相应的伯胺。通过采用这种微波辅助的方法，反应的速率和产率得到了显着提高，这对于制备具有生物学和药学活性的高密度官能化分子可能是有价值的。
• RhCl3-catalysed amide bond formation under mild conditions
  作者：Yoshinori Yamamoto、Hidetaka Yatagai、Kazuhiro Maruyama

  DOI：10.1039/c39800000835

  日期：——

  The reaction of carboxylic acid esters with amines is accelerated in the presence of catalytic amounts of RhCl3.3H2O at a reasonably low temperature; optically active 2,5-dioxopiperazines can be synthesized in high yield from the corresponding amino-acid esters using this procedure.

  在适量的低温下，在催化量的RhCl 3 .3H 2 O的存在下，羧酸酯与胺的反应得以加速。可以使用该方法由相应的氨基酸酯高产率地合成旋光的2，5-二氧杂哌嗪。
• Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides
  作者：Christopher Bérubé、Xavier Barbeau、Sébastien Cardinal、Pierre-Luc Boudreault、Corinne Bouchard、Nicolas Delcey、Patrick Lagüe、Normand Voyer

  DOI：10.1080/10610278.2016.1236197

  日期：2017.5.4

  We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.[GRAPHICS].