(3R,6S)-1,6-3,4-bis(propylidene)-1,4-piperazine-2,5-dione | 36588-48-4

• 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: (3R,6S)-1,6-3,4-bis(propylidene)-1,4-piperazine-2,5-dione
• 英文别名: (3S,6R)-1,6-3,4-bis(propylidene)-1,4-piperazine-2,5-dione；octahydropyrrolo[1,2-a:1',2'-d]pyrazin-5,10-dione；cyclo(-L-Pro-D-Pro-)；c(D-Pro–L-Pro)；cyclo(D-Pro-L-Pro)；cyclo[D-Pro-L-Pro]；(3R,9S)-1,7-diazatricyclo[7.3.0.03,7]dodecane-2,8-dione
• CAS: 36588-48-4；53990-72-0
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: BKASXWPLSXFART-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 在 钯 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 114.0h， 生成 (3R,6S)-1,6-3,4-bis(propylidene)-1,4-piperazine-2,5-dione
  参考文献：
  名称：

  Facile Synthesis of Cyclic Dipeptides and Detection of Racemization

  摘要：

  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。

  DOI：

  10.1246/bcsj.56.568

文献信息

• Synthesis of Optically Active <b><i>C</i></b>-Allylglycine Derivatives and Conversion into Isoquinolones
  作者：Udo Nubbemeyer、Nong Zhang

  DOI：10.1055/s-2002-19804

  日期：——

  synthesized via an auxiliary controlled diastereoselective aza-Claisen rearrangement. The stereodirecting unit is placed on an auxiliary derived from commercially available (S)-proline. After N-allylation. the obtained optically active allylamines were reacted with various N-protected glycyl fluorides to give the (2R)-C-allylglycyl amides in good yields. The diastereoselectivity of the asymmetric allylation

  C-烯丙基甘氨酰胺可以通过辅助控制的非对映选择性氮杂-克莱森重排有效合成。立体定向单元放置在衍生自市售 (S)-脯氨酸的辅助物上。N-烯丙基化后。获得的光学活性烯丙胺与各种N-保护的甘氨酰氟反应以良好的收率得到(2R)-C-烯丙基甘氨酰胺。不对称烯丙基化的非对映选择性在 1:1 和 >1:15 之间变化，具体取决于 N-保护基团、助剂和反应温度。同样，C-烯丙基甘氨酸衍生物可用作肽合成中的单体以合成(R)-脯氨酸衍生物或手性异喹诺酮类；后者应作为生物碱总合成的组成部分。
• Molecular Capture and Conformational Change of Diketopiperazines Containing Proline Residues by Epigallocatechin-3-&lt;i&gt;O&lt;/i&gt;-gallate in Water
  作者：Takashi Ishizu、Miku Tokunaga、Moeka Fukuda、Mana Matsumoto、Takeshi Goromaru、Soushi Takemoto

  DOI：10.1248/cpb.c21-00047

  日期：2021.6.1

  hydrophobicity of the side chain of the amino acid residue of cyclo(Pro-Xxx) led to a higher molecular capture ability. Furthermore, the molecular capture ability decreased when the side chain of the amino acid residue had a hydrophilic hydroxyl group. When diketopiperazine cyclo(Pro-Xxx), excluding cyclo(D-Pro-L-Ala), was taken into the hydrophobic space formed by the three aromatic A, B, and B′ rings of EGCg

  将二酮哌嗪环（Pro-Xxx）（Xxx：氨基酸残基）的水溶液添加到（-）-表没食子儿茶素-3- O的水溶液中-gallate (EGCg) 导致 EGCg 和环 (Pro-Xxx) 的复合物沉淀。使用 EGCg 的环 (Pro-Xxx) 的分子捕获能力通过与 EGCg 复合物的沉淀物中包含的环 (Pro-Xxx) 的量与所用的总环 (Pro-Xxx) 的量之比来评估。cyclo(Pro-Xxx) 氨基酸残基侧链的更强疏水性导致更高的分子捕获能力。此外，当氨基酸残基的侧链具有亲水性羟基时，分子捕获能力降低。当不包括环(D-Pro-L-Ala)的二酮哌嗪环(Pro-Xxx)被带入EGCg的三个芳香A、B和B'环形成的疏水空间中，形成复合物时，它们的构象保持在疏水空间中。基于核奥弗豪泽效应 (NOE) 测量，2 O 是轴向的，而环（L-Pro-L-Ala）是赤道的。当环(D-Pro-L-Ala)
• 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].
• Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens
  作者：Gaëlle Simon、Christopher Bérubé、Normand Voyer、Daniel Grenier

  DOI：10.1016/j.bmc.2018.11.042

  日期：2019.6

  Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure-activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.
• 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。