cyclo-(L-Val-L-Leu) | 35590-78-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: cyclo-(L-Val-L-Leu)
• 英文别名: Cyclo-(L-Val-L-Leu)；(3S,6R)-3-(2-methylpropyl)-6-propan-2-ylpiperazine-2,5-dione
• CAS: 35590-78-4
• 化学式: C₁₁H₂₀N₂O₂
• 分子量: 212.292
• InChiKey: UPOUGDHEEGKEGS-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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-(L-Val-L-Leu) 在 盐酸 、 水 作用下， 生成 L-缬氨酸 、 L-亮氨酸
  参考文献：
  名称：

  Secondary metabolites from the endophytic fungiPenicillium polonicumandAspergillus fumigatus

  摘要：

  Two new compounds, rhodostegone (1) from endophytic fungus Penicillium polonicum and cyclo-(l-Val-l-Leu) (2) from Aspergillus fumigatus, together with six known diketopiperazines (3-8), were isolated. The structures of these compounds were characterized through a combination of extensive IR, MS, NMR, and CD analysis.

  DOI：

  10.1080/10286020.2013.780349
• 作为产物：
  描述：

  BOC-L-亮氨酸 、 Boc-D-缬氨酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 cyclo-(L-Val-L-Leu)
  参考文献：
  名称：

  Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2018.11.042

文献信息

• 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.
• Secondary metabolites from the endophytic fungi<i>Penicillium polonicum</i>and<i>Aspergillus fumigatus</i>
  作者：Guang-Zhi Ding、Jing Liu、Jia-Ming Wang、Lei Fang、Shi-Shan Yu

  DOI：10.1080/10286020.2013.780349

  日期：2013.5

  Two new compounds, rhodostegone (1) from endophytic fungus Penicillium polonicum and cyclo-(l-Val-l-Leu) (2) from Aspergillus fumigatus, together with six known diketopiperazines (3-8), were isolated. The structures of these compounds were characterized through a combination of extensive IR, MS, NMR, and CD analysis.