(3R,6R)-3,6-diisobutylpiperazine-2,5-dione | 952-43-2

• 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,6R)-3,6-diisobutylpiperazine-2,5-dione
• 英文别名: cyclo-D-Leu-D-Leu；cyclo(D-L-D-L)；cyclo[D-Leu-D-Leu]；(3R)-cis-3,6-diisobutyl-piperazine-2,5-dione；(3R)-cis-3,6-Diisobutyl-piperazin-2,5-dion；(R)-cis-3,6-Diisobutyl-piperazin-2,5-dion；cyclo(Leu-Leu)；(3R,6R)-3,6-bis(2-methylpropyl)piperazine-2,5-dione
• CAS: 952-43-2
• 化学式: C₁₂H₂₂N₂O₂
• 分子量: 226.319
• InChiKey: XWYXUMDVQIOAPR-NXEZZACHSA-N

物化性质

• 沸点：
  445.2±38.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (3R,6R)-3,6-diisobutylpiperazine-2,5-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,5R)-2,5-diisobutylpiperazine
  参考文献：
  名称：

  Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities

  摘要：

  With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.051
• 作为产物：
  描述：

  2,5-Dichloro-3,6-diisobutylpyrazine 在 platinum(IV) oxide 、 镍 盐酸 、 dipotassium peroxodisulfate 、 硫酸 、 氢气 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 25.0~110.0 ℃ 、392.24 kPa 条件下， 反应 52.0h， 生成 (3R,6R)-3,6-diisobutylpiperazine-2,5-dione
  参考文献：
  名称：

  Ohta, Akihiro; Yamamoto, Fusako; Arimura, Yasuhiko, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 781 - 784

  摘要：

  DOI：
• 作为试剂：
  描述：

  反式-查耳酮 在 (3R,6R)-3,6-diisobutylpiperazine-2,5-dione 、 双氧水 、 sodium hydroxide 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以70%的产率得到
  参考文献：
  名称：

  Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides

  摘要：

  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].

  DOI：

  10.1080/10610278.2016.1236197

文献信息

• Peptide bond formation by aminolysin-A catalysis: A simple approach to enzymatic synthesis of diverse short oligopeptides and biologically active puromycins
  作者：Hirokazu Usuki、Yukihiro Yamamoto、Jiro Arima、Masaki Iwabuchi、Shozo Miyoshi、Teruhiko Nitoda、Tadashi Hatanaka

  DOI：10.1039/c0ob00403k

  日期：——

  peptide bonds to give linear homo-oligopeptides, hetero-dipeptides, and cyclic dipeptides using cost-effective substrates in a one-pot reaction. Aminolysin-A can recognize several C-terminal-modified amino acids, including the L- and D-forms, as acyl donors as well as free amines, including amino acids and puromycin aminonucleoside, as acyl acceptors. The absence of amino acid esters prevents the formation

  新S9系列的氨肽酶从嗜热放线菌衍生Acidothermus了解纤维素被催化丝氨酸的定点突变克隆和工程化到transaminopeptidase 491到半胱氨酸。经过工程改造的生物催化剂，称为氨基溶素A，可以在一锅反应中使用经济高效的底物来催化肽键的形成，从而生成线性同型寡肽，杂二肽和环状二肽。氨基溶素A可以识别多个C末端修饰的氨基酸（包括L-和D-形式）作为酰基供体，以及游离胺（包括氨基酸和嘌呤霉素氨基核苷）作为酰基受体。氨基酸酯的缺乏阻止了肽的形成。因此，反应机理涉及氨解而不是水解的逆反应。氨基溶素系统将是通过简单方法制备结构多样的肽模拟物的有益工具。
• Engineered transaminopeptidase, aminolysin-S for catalysis of peptide bond formation to give linear and cyclic dipeptides by one-pot reaction
  作者：Hirokazu Usuki、Yoshiko Uesugi、Jiro Arima、Yukihiro Yamamoto、Masaki Iwabuchi、Tadashi Hatanaka

  DOI：10.1039/b914320c

  日期：——

  Aminopeptidase from Streptomyces thermocyaneoviolaceus NBRC14271 was engineered into transaminopeptidase and used to catalyze an aminolysis reaction to give linear and cyclic dipeptides from cost-effective substrates such as the ester derivatives of amino acids.

  将来自热链霉菌NBRC14271的氨肽酶工程化为转氨肽酶，并用于催化氨解反应，以从成本有效的底物（例如氨基酸的酯衍生物）得到线性和环状的二肽。
• 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.
• Fischer,E.; Koelker, Justus Liebigs Annalen der Chemie, 1907, vol. 354, p. 40,44, 46
  作者：Fischer,E.、Koelker

  DOI：——

  日期：——
• Biomimetic epoxidation in aqueous media catalyzed by cyclic dipeptides
  作者：Christopher Bérubé、Normand Voyer

  DOI：10.1080/00397911.2016.1141428

  日期：2016.3.3

  We have developed a practical epoxidation of electron-deficient enones in aqueous media using cyclic dipeptides as bioinspired green catalyst. Optimizing the reaction conditions in a triphasic system led to efficient conditions providing epoxides with good enantioselectivities. Depending on the catalyst substituent chirality, both enantiomers are obtained. The cyclic rigidity impacts significantly the enantioselectivity.