(+)-L-[S-(4-hydroxybenzyl)]cysteinylglycine

• 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: (+)-L-[S-(4-hydroxybenzyl)]cysteinylglycine
• 化学式: C₁₂H₁₆N₂O₄S
• 分子量: 284.336
• InChiKey: XYPPAROUTXMOQS-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112.65
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  H-半胱氨酸-甘氨酸-OH 、 对羟基苯甲醇 在 盐酸 作用下， 以 水 为溶剂， 反应 0.33h， 生成 (+)-L-[S-(4-hydroxybenzyl)]cysteinylglycine
  参考文献：
  名称：

  4-Hydroxybenzyl-substituted glutathione derivatives fromGastrodia elata

  摘要：

  Seven new 4-hydroxybenzyl-substituted glutathione derivatives (2-8), together with a known analogue (1), were isolated from the aqueous extract of Gastrodia elata Blume rhizomes. Their structures were determined by using spectroscopic and chemical methods. The absolute configurations of 1-8 were assigned by using Marfey's method, combined with comparing the NMR and CD spectroscopic data of sulfoxide moieties in 3-6 with those of S-(4-hydroxybenzyl)cysteine sulfoxide stereoisomers (9-12) synthesized as authentic samples. The configurations of 9-12 were confirmed by electronic CD calculations based on the quantum-mechanical time-dependent density functional theory. Furthermore, the structures of 1, 3, 5, 7, and 8 were verified by synthesis. Compound 3 was active against serum deprivation-induced PC12 cell damage and synthetic 9-14 exhibited activity against Fe2+-cysteine induced rat liver microsomal lipid peroxidation.

  DOI：

  10.1080/10286020.2015.1040000

文献信息

• 4-Hydroxybenzyl-substituted glutathione derivatives from<i>Gastrodia elata</i>
  作者：Qing-Lan Guo、Ya-Nan Wang、Cheng-Gen Zhu、Ming-Hua Chen、Zhi-Bo Jiang、Nai-Hong Chen、Xiu-Yun Song、Mei-Jin Zhang、Jian-Gong Shi

  DOI：10.1080/10286020.2015.1040000

  日期：2015.5.4

  Seven new 4-hydroxybenzyl-substituted glutathione derivatives (2-8), together with a known analogue (1), were isolated from the aqueous extract of Gastrodia elata Blume rhizomes. Their structures were determined by using spectroscopic and chemical methods. The absolute configurations of 1-8 were assigned by using Marfey's method, combined with comparing the NMR and CD spectroscopic data of sulfoxide moieties in 3-6 with those of S-(4-hydroxybenzyl)cysteine sulfoxide stereoisomers (9-12) synthesized as authentic samples. The configurations of 9-12 were confirmed by electronic CD calculations based on the quantum-mechanical time-dependent density functional theory. Furthermore, the structures of 1, 3, 5, 7, and 8 were verified by synthesis. Compound 3 was active against serum deprivation-induced PC12 cell damage and synthetic 9-14 exhibited activity against Fe2+-cysteine induced rat liver microsomal lipid peroxidation.