stictamide B | 1301133-26-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: stictamide B
• 英文别名: (2S)-2-[[(3S,4S)-4-[[(2R)-5-(diaminomethylideneamino)-2-[4-(4-hydroxyphenyl)butanoylamino]pentanoyl]amino]-3-hydroxy-5-phenylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
• CAS: 1301133-26-5
• 化学式: C₃₆H₄₆N₆O₈
• 分子量: 690.797
• InChiKey: ORWSPLPFCCECQV-BHSUFKTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  250
• 氢给体数：
  9
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  stictamide B 、 NAlpha-(5-氟-2,4-二硝基苯基)-L-亮氨酰胺 在 盐酸 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 10.05h， 生成 L-Tyr-N-L-FDLA 、 L-Tyr-O-L-FDLA 、 (3S,4S)-Ahppa-L-FDLA 、 D-Arg-L-FDLA
  参考文献：
  名称：

  Stictamides A−C, MMP12 Inhibitors Containing 4-Amino-3-hydroxy-5-phenylpentanoic Acid Subunits

  摘要：

  An extensive study of the secondary metabolites produced by a new Sticta sp. of lichen has led to the isolation of three new compounds containing the 4-amino-3-hydroxy-5-phenylpentanoic acid residue (Ahppa). The structures of stictamides A-C (1-3) were assigned by 2D NMR spectroscopic and chemical methods. Due to extensive epimerization of the Ahppa residue observed after acid hydrolysis, the configuration of this unit was deduced through conversion of 1 to an appropriate derivative and application of our recently developed statine NMR database. Evaluation of stictamide A against a panel of disease-relevant proteases showed that it inhibited MMP12 at 2.3 mu M and significantly reduced invasion in the human glioma cell line U87MG. Docking studies suggest that stictamide A inhibits MMP12 by a non-zinc-binding mechanism.

  DOI：

  10.1021/jo200241h

文献信息

• Stictamides A−C, MMP12 Inhibitors Containing 4-Amino-3-hydroxy-5-phenylpentanoic Acid Subunits
  作者：Zhibin Liang、Analia Sorribas、Florian J. Sulzmaier、Jorge I. Jiménez、Xin Wang、Thomas Sauvage、Wesley Y. Yoshida、Guangyi Wang、Joe W. Ramos、Philip G. Williams

  DOI：10.1021/jo200241h

  日期：2011.5.20

  An extensive study of the secondary metabolites produced by a new Sticta sp. of lichen has led to the isolation of three new compounds containing the 4-amino-3-hydroxy-5-phenylpentanoic acid residue (Ahppa). The structures of stictamides A-C (1-3) were assigned by 2D NMR spectroscopic and chemical methods. Due to extensive epimerization of the Ahppa residue observed after acid hydrolysis, the configuration of this unit was deduced through conversion of 1 to an appropriate derivative and application of our recently developed statine NMR database. Evaluation of stictamide A against a panel of disease-relevant proteases showed that it inhibited MMP12 at 2.3 mu M and significantly reduced invasion in the human glioma cell line U87MG. Docking studies suggest that stictamide A inhibits MMP12 by a non-zinc-binding mechanism.