环(L-苯丙氨酰-反式-4-羟基-L-脯氨酸) | 118477-06-8

• 物质功能分类: 天然产物 - 生物碱
• 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
• 中文名称: 环(L-苯丙氨酰-反式-4-羟基-L-脯氨酸)
• 英文名称: (3S,7R,8aS)-hexahydro-7-hydroxy-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
• 英文别名: hexahydro-7-hydroxy-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione；cyclo-(L-phenylalanine-trans-4-hydroxy-L-proline)；cyclo(4-trans-hydroxy-L-proline-L-phenylalanine)；cyclo(trans-4-hydroxy-L-proline-L-phenylalanine)；cyclo(L-phenylalanyl-trans-4-hydroxy-L-proline)；cyclo(trans-4-hydroxy-L-prolyl-L-phenylalanine)；cyclo(L-Phe-trans-4-hydroxy-L-Pro)；(3S,7R,8aS)-3-benzyl-7-hydroxy-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 118477-06-8
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: PYQJYHACQOBZLF-WOPDTQHZSA-N

物化性质

• 沸点：
  568.2±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  环(L-苯丙氨酰-反式-4-羟基-L-脯氨酸) 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 盐酸 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 25.0h， 生成 L-Phe-L-FDAA 、
  参考文献：
  名称：

  Acaricidal Activity of Cyclodipeptides from Bacillus amyloliquefaciens W1 against Tetranychus urticae

  摘要：

  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.

  DOI：

  10.1021/acs.jafc.8b03806

文献信息

• ANTIFUNGAL COMPOSITIONS CONTAINING THE ENDOPHYTE FUNGUS ALTERNARIA ALTERNATA AND OR ITS METABOLITES, AS ANTAGONIST AGENTS OF PLASMOPARA VITICOLA
  申请人：Musetti Rita

  公开号：US20090257984A1

  公开（公告）日：2009-10-15

  The present invention relates to compositions containing the fungus Alternaria alternata and/or the secondary metabolites thereof, which belong to the family of the diketopiperazines (DKPs), for controlling the pathogen fungus Plasmopara viticola.
• 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.