cystargolide B

• 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: cystargolide B
• 英文别名: Cystargolide B；(2S)-3-methyl-2-[[(2S)-3-methyl-2-[(4-oxo-3-propan-2-yloxetane-2-carbonyl)amino]butanoyl]amino]butanoic acid
• 化学式: C₁₇H₂₈N₂O₆
• 分子量: 356.419
• InChiKey: PDPYJYDVMZXUKQ-ZFQMDJOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cystargolide B 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 L-缬氨酸
  参考文献：
  名称：

  Cystargolides, 20S Proteasome Inhibitors Isolated from Kitasatospora cystarginea

  摘要：

  Two novel beta-lactone-containing natural products, cystargolides A (1) and B (2), were isolated from the actinomycete Kitasatospora cystarginea. The production of these two natural products was highlighted using a methodology associating liquid chromatography-high-resolution mass spectrometry (LC-HRMS) analysis and the statistical analysis tool principal component analysis (PCA). Their structures were elucidated by interpretation of NMR experiments and tandem mass spectrometry. The absolute configurations of the amino acid residues were determined using Marfeys method, and the relative configurations of the beta-lactone substituents were determined on the basis of the vicinal (3)J(HH) coupling value. Due to the presence of the beta-lactone, 1 and 2 were evaluated for their ability to inhibit the human 20S proteasome. 1 and 2 both inhibited the 20S proteasome in vitro with IC50 values of 0.35 and 0.93 mu M, respectively.

  DOI：

  10.1021/np501060k

文献信息

• [EN] CYSTARGOLIDE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE CYSTARGOLIDE ET LEURS UTILISATIONS
  申请人：UNIV PRINCE EDWARD ISLAND

  公开号：WO2016123699A1

  公开（公告）日：2016-08-11

  There is provided herein compounds of formula I, wherein R1 is H or linear or branched C1-C6 lower alkyl; R2 is H, linear or branched C1-C6 lower alkyl, or a proteinogenic amino acid side chain; R3 is H, linear or branched C1-C6 lower alkyl, or a proteinogenic amino acid side chain; R4 is -OH or -O-R5 wherein R5 is linear or branched C1-C6 lower alkyl; and each R6 is independently H or -CH3; or a pharmaceutically acceptable prodrug, salt, or ester thereof. Compositions containing said compounds, and uses thereof, are also provided. (I)
• Cystargolides, 20S Proteasome Inhibitors Isolated from <i>Kitasatospora cystarginea</i>
  作者：Krista A. Gill、Fabrice Berrué、Jennifer C. Arens、Gavin Carr、Russell G. Kerr

  DOI：10.1021/np501060k

  日期：2015.4.24

  Two novel beta-lactone-containing natural products, cystargolides A (1) and B (2), were isolated from the actinomycete Kitasatospora cystarginea. The production of these two natural products was highlighted using a methodology associating liquid chromatography-high-resolution mass spectrometry (LC-HRMS) analysis and the statistical analysis tool principal component analysis (PCA). Their structures were elucidated by interpretation of NMR experiments and tandem mass spectrometry. The absolute configurations of the amino acid residues were determined using Marfeys method, and the relative configurations of the beta-lactone substituents were determined on the basis of the vicinal (3)J(HH) coupling value. Due to the presence of the beta-lactone, 1 and 2 were evaluated for their ability to inhibit the human 20S proteasome. 1 and 2 both inhibited the 20S proteasome in vitro with IC50 values of 0.35 and 0.93 mu M, respectively.