{[(2R)-2-azaniumyl-3-{[(1E)-N-hydroxy-2-(1H-indol-3-yl)ethanimidoyl]sulfanyl}propanoyl]amino}acetate

• 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: {[(2R)-2-azaniumyl-3-{[(1E)-N-hydroxy-2-(1H-indol-3-yl)ethanimidoyl]sulfanyl}propanoyl]amino}acetate
• 英文别名: 2-[[(2R)-2-azaniumyl-3-[(E)-N-hydroxy-C-(1H-indol-3-ylmethyl)carbonimidoyl]sulfanylpropanoyl]amino]acetate
• 化学式: C15H18N4O4S
• 分子量: 350.4
• InChiKey: PQEHILHGDWJAOT-YODGCNRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  166
• 氢给体数：
  5
• 氢受体数：
  7

文献信息

• Cytosolic γ-Glutamyl Peptidases Process Glutathione Conjugates in the Biosynthesis of Glucosinolates and Camalexin in <i>Arabidopsis</i>    
  作者：Fernando Geu-Flores、Morten Emil Møldrup、Christoph Böttcher、Carl Erik Olsen、Dierk Scheel、Barbara Ann Halkier

  DOI：10.1105/tpc.111.083998

  日期：2011.6.1

  The defense-related plant metabolites known as glucosinolates play important roles in agriculture, ecology, and human health. Despite an advanced biochemical understanding of the glucosinolate pathway, the source of the reduced sulfur atom in the core glucosinolate structure remains unknown. Recent evidence has pointed toward GSH, which would require further involvement of a GSH conjugate processing enzyme. In this article, we show that an Arabidopsis thaliana mutant impaired in the production of the γ-glutamyl peptidases GGP1 and GGP3 has altered glucosinolate levels and accumulates up to 10 related GSH conjugates. We also show that the double mutant is impaired in the production of camalexin and accumulates high amounts of the camalexin intermediate GS-IAN upon induction. In addition, we demonstrate that the cellular and subcellular localization of GGP1 and GGP3 matches that of known glucosinolate and camalexin enzymes. Finally, we show that the purified recombinant GGPs can metabolize at least nine of the 10 glucosinolate-related GSH conjugates as well as GS-IAN. Our results demonstrate that GSH is the sulfur donor in the biosynthesis of glucosinolates and establish an in vivo function for the only known cytosolic plant γ-glutamyl peptidases, namely, the processing of GSH conjugates in the glucosinolate and camalexin pathways.

  被称为葡萄糖硫醇苷的防御相关植物代谢物在农业、生态和人类健康中都扮演着重要角色。尽管对葡萄糖硫醇苷途径的生物化学理解已经很先进，但核心葡萄糖硫醇苷结构中还原硫原子的来源仍然未知。最近的证据指出了GSH，这将需要进一步涉及GSH结合物处理酶。在本文中，我们展示了一种Arabidopsis thaliana突变体，其生产γ-谷氨酰肽酶GGP1和GGP3受损，其葡萄糖硫醇苷水平发生改变，并积累了多达10个相关的GSH结合物。我们还展示了双突变体在产生卡马雷辛方面存在障碍，并在诱导后积累高量的卡马雷辛中间体GS-IAN。此外，我们证明了GGP1和GGP3的细胞和亚细胞定位与已知的葡萄糖硫醇苷和卡马雷辛酶相匹配。最后，我们展示了纯化的重组GGP能够代谢至少10个与葡萄糖硫醇苷相关的GSH结合物以及GS-IAN。我们的结果表明，GSH是葡萄糖硫醇苷生物合成中的硫供体，并为唯一已知的细胞质植物γ-谷氨酰肽酶建立了在体功能，即处理葡萄糖硫醇苷和卡马雷辛途径中的GSH结合物。