L-hydroxyprolyl-L-proline anhydride | 36099-80-6

• 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: L-hydroxyprolyl-L-proline anhydride
• 英文别名: Cyclic-prolyl-hydroxyproline；(3S,5R,9S)-5-hydroxy-1,7-diazatricyclo[7.3.0.03,7]dodecane-2,8-dione
• CAS: 36099-80-6
• 化学式: C₁₀H₁₄N₂O₃
• 分子量: 210.233
• InChiKey: NUWIAVSANIAUAA-CSMHCCOUSA-N

物化性质

• 沸点：
  481.1±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  15
• 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：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-hydroxyprolyl-L-proline anhydride 在 碘 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.83h， 生成 (3S,6S)-1-acetoxymethyl-6-(2-morpholinoethyl)-3,4-(trimethylene) piperazine-2,5-dione
  参考文献：
  名称：

  通过定制化单元的选择性修饰合成具有定制N和α链的二酮哌嗪支架

  摘要：

  在DKP基板中对Hyp可定制单元的选择性操作允许生成具有四个空间定向的量身定制链的刚性支架。关键步骤是多米诺骨牌断裂-氧化过程，该过程允许生成N取代的DKP。本文描述了这种方法的通用性，其以高光学纯度生产用于材料和药物发现的支架。

  DOI：

  10.1002/adsc.202000470
• 作为产物：
  描述：

  Boc-Pro-Hyp-OMe 在 乙酰氯 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.0h， 以87%的产率得到L-hydroxyprolyl-L-proline anhydride
  参考文献：
  名称：

  通过定制化单元的选择性修饰合成具有定制N和α链的二酮哌嗪支架

  摘要：

  在DKP基板中对Hyp可定制单元的选择性操作允许生成具有四个空间定向的量身定制链的刚性支架。关键步骤是多米诺骨牌断裂-氧化过程，该过程允许生成N取代的DKP。本文描述了这种方法的通用性，其以高光学纯度生产用于材料和药物发现的支架。

  DOI：

  10.1002/adsc.202000470

文献信息

• Acaricidal Activity of Cyclodipeptides from <i>Bacillus amyloliquefaciens</i> W1 against <i>Tetranychus urticae</i>
  作者：Xing-Yu Li、Yue-Hu Wang、Jun Yang、Wen-Yan Cui、Peng-Jie He、Shahzad Munir、Peng-Fei He、Yi-Xin Wu、Yue-Qiu He

  DOI：10.1021/acs.jafc.8b03806

  日期：2018.10.3

  Bioassay-guided fractionation of the supernatant of the biocontrol strain Bacillus amyloliquefaciens W1 led to the isolation of eight acaricidal cyclodipeptides from the active fractions by column chromatography separation and HPLC purification. The chemical structures of these compounds were identified as cyclo-(Gly-L-Phe), 2, cyclo-(L-Phe-trans-4-OH-L-Pro), 3, cyclo-(Gly-L-Tyr), 4, cyclo-(L-Ala-L-Pro), 5, cyclo-(L-Pro-trans-4-OH-L-Pro), 6, cyclo-(Gly-L-Pro), 7, cyclo-(L-Pro-L-Pro), 8, and cyclo-(L-Tyr-trans-4-OH-L-Pro), 9. Those cyclodipeptides displayed significant acaricidal activities with LC50 values of 13.85-98.24 mu M. Cyclo-(L-Tyr-trans-4-OH-L-Pro) (LC50 13.85 mu M) was five times more effective than the positive control abamectin (LC50 72.06 mu M). The results indicated that the hydroxyl group is an important component. This is the first report on the acaricidal capabilities of cyclodipeptides against Tetranychus urticae. The results revealed that the acaricidal activity of the biocontrol strain B. amyloliquefaciens W1 was dependent on its constituent cyclodipeptides, which have the potential to be safe and environmentally friendly acaricides.
• Highly Diastereoselective Desymmetrizations of Cyclo(Pro,Pro):  An Enantioselective Strategy toward Phakellstatin and Phakellin
  作者：Karine G. Poullennec、Anna T. Kelly、Daniel Romo

  DOI：10.1021/ol026140q

  日期：2002.8.1

  [GRAPHICS]Monoenolates of C-2-symmetric, proline-derived piperazine-2,5-diones were generated and trapped with a variety of electrophiles to produce, in a highly diastereoselective fashion, functionalized diketopiperazines (DKPs). These reactions provide the basis for an asymmetric, desymmetrization strategy toward the marine alkaloids phakellstatin and phakellin, The relative stereochemistry of the functionalized DKPs was confirmed by single-crystal X-ray analysis and/or NOE experiments. Bis-functionalization of the DKPs was also found to proceed with high levels of diastereoselectivity.
• Bioactive compounds produced in animal tissues (I); two diketopiperadine plant growth regulators containing hydroxyproline isolated from rabbit skin tissue extract
  作者：Kazuharu Ienaga、Ko Nakamura、Toshio Goto

  DOI：10.1016/s0040-4039(00)95347-4

  日期：1987.1
• Hydroxyproline-containing diketopiperazines inducing drought resistance in rice
  作者：Kazuharu Ienaga、Ko Nakamura、Masaharu Kurohashi、Tetsu Nakanishi、Takao Ichii

  DOI：10.1016/0031-9422(90)89005-t

  日期：1990.1
• UEHNAGA, KADZUXARU;NAKAMURA, TSUTOMU
  作者：UEHNAGA, KADZUXARU、NAKAMURA, TSUTOMU

  DOI：——

  日期：——