(3R,8S)-3-((carboxymethyl)carbamoyl)-5-oxo-3,4,5,6,7,8-hexahydro-2H-[1,3,8]thiadiazecino[2,3-a]isoindole-8-carboxylic acid | 121321-76-4

• 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: (3R,8S)-3-((carboxymethyl)carbamoyl)-5-oxo-3,4,5,6,7,8-hexahydro-2H-[1,3,8]thiadiazecino[2,3-a]isoindole-8-carboxylic acid
• CAS: 121321-76-4
• 化学式: C₁₈H₁₉N₃O₆S
• 分子量: 405.431
• InChiKey: KQNCJEVDTYUNCW-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  137.73
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  L-谷胱甘肽 (氧化型) 、 邻苯二甲醛 在 盐酸 、 硼酸 、 2-巯基乙醇 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.03h， 生成 (3R,8S)-3-((carboxymethyl)carbamoyl)-5-oxo-3,4,5,6,7,8-hexahydro-2H-[1,3,8]thiadiazecino[2,3-a]isoindole-8-carboxylic acid
  参考文献：
  名称：

  Drought stress increases the production of 5-hydroxynorvaline in two C4 grasses

  摘要：

  Plants produce various compounds in response to water deficit. Here, the presence and identification of a drought-inducible non-protein amino acid in the leaves of two C-4 grasses is first reported. The soluble amino acids extracted from the leaves of three different species were measured by high-performance liquid chromatography of derivatives formed with o-phthaldialdehyde and beta-mercaptoethanol. One amino acid that increased in amount with drought stress had a retention time not corresponding to any common amino acid. Its identity was determined by metabolite profiling, using H-1 NMR and GC-MS. This unusual amino acid was present in the dehydrated leaves of Cynodon dactylon (L) Pets. and Zoysia japonica Steudel, but was absent from Paspalum dilatatum Poir. Its identity as 2-amino-5-hydroxypentanoic acid (5-hydroxynorvaline, 5-HNV) was confirmed by synthesis and co-chromatography of synthetic and naturally occurring compounds. The amount of 5-HNV in leaves of the more drought tolerant C-4 grasses, C. dactylon and Z. japonica, increased with increasing water deficit; therefore, any benefits from this unusual non-protein amino acid for drought resistance should be further explored. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.03.001

文献信息

• HPLC study of the host–guest complexation between fluorescent glutathione derivatives and β-cyclodextrin
  作者：Stéphanie Marchand、Aldona Guzek、Pierre Leroy

  DOI：10.1007/s10847-009-9619-5

  日期：2010.4

  RP-HPLC and the van’t Hoff law were used to study the association in which β-cyclodextrin forms inclusion complexes with aminothiol–phthaldialdehyde derivatives prepared from either glutathione (GSH) or γ-glutamylcysteine (γ-glucys) and either naphthalene-2,3-dicarboxaldehyde (NDA) or o-phthaldialdehyde (OPA). Elution was carried out at pH 8.5, the derivatization pH which gave the highest fluorescence signal during batch experiments. The variation of the retention factor (k) was monitored as a function of column temperature (10–35 °C) and β-cyclodextrin concentration (0–5 mM) in the mobile phase. Apparent binding constants, enthalpy and entropy were calculated from van’t Hoff plots for the complexation reaction. These data lay the groundwork for the improvement of high throughput GSH quantification methods using fluorimetry in biological and vegetal samples.

  采用反相高效液相色谱法（RP-HPLC）和范特霍夫定律研究了β-环糊精与谷胱甘肽（GSH）或γ-谷氨酰半胱氨酸（γ-glucys）与萘-2,3-二甲醛（NDA）或邻苯二甲醛（OPA）的氨基硫醇-酞醛衍生物形成的包合物。洗脱在pH 8.5下进行，这是批量实验中获得最高荧光信号的衍生化pH值。监测保留因子（k）随柱温（10–35°C）和流动相中β-环糊精浓度（0–5 mM）的变化。从包合物反应的范特霍夫图中计算出表观结合常数、焓和熵。这些数据为进一步改进利用荧光法在生物和植物样品中高通量定量谷胱甘肽的方法奠定了基础。