丙基半胱氨酸-磺基氧化 | 17795-25-4

• 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
• 中文名称: 丙基半胱氨酸-磺基氧化
• 英文名称: PCSO
• 英文别名: (+/-)-n-Propyl-L-cysteinsulfoxid；2-Azaniumyl-3-propylsulfinylpropanoate
• CAS: 17795-25-4
• 化学式: C₆H₁₃NO₃S
• 分子量: 179.24
• InChiKey: JZKMSAGUCSIIAH-UHFFFAOYSA-N

物化性质

• 沸点：
  412.7±40.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  161-162°C

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  99.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙基半胱氨酸-磺基氧化 在 water extract of garlic 作用下， 以 水 为溶剂， 以65%的产率得到S-丙基丙烷-1-硫代亚磺酸盐
  参考文献：
  名称：

  A Tissue Homogenate Method To Prepare Gram-Scale Allium Thiosulfinates and Their Disulfide Conjugates with Cysteine and Glutathione

  摘要：

  The health benefits of Allium vegetables are widely attributed to the enzyme-derived organosulfur compounds called thiosulfinates (TS). However, the lack of a suitable method to prepare TS in good yields has hampered the evaluation of their biological activities. This paper describe a simple enzymatic method using Allium tissue homogenates as a reaction system to prepare gram-scale TS, including those enriched in 1-propenyl groups, which are particularly difficult to obtain. This method is simple, easy to scale up, and requires no column purification step, making it suitable for practical large-scale production of Allium TS. The prepared TS were further utilized to prepare the disulfide conjugates with cysteine and glutathione (CySSR and GSSR, R = methyl, ethyl, propyl, 1-propenyl, and allyl), which are the presumptive metabolites of TS. Among all of the Allium CySSR and GSSR conjugates, the newly prepared glutathione conjugate with 1-propenyl TS, GSSPe, showed the most potent effect to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7).

  DOI：

  10.1021/jf4003818

文献信息

• IMPROVEMENTS IN OR RELATING TO ALLIUM EXTRACTS
  申请人：LEPTREX LTD.

  公开号：US20160151324A1

  公开（公告）日：2016-06-02

  Improvements in or relating to Allium extracts. In particular, improvements in or relating to extending the therapeutic half-life or duration of Allium extracts. The invention further relates to the synthesis of methyl methyl thiosulfinate in a mixture with varying molar or mass ratios depending on the reaction conditions, in particular from either methiin or alliin alone or a mixture of both. Methods of treatment methicillin-resistant Staphylococcus aureus are also provided. Also provided is a kit comprising methiin in a first container and alliin in a second container.

  与Allium提取物相关的改进。特别是，改进或与延长Allium提取物的治疗半衰期或持续时间有关。该发明还涉及在混合物中合成甲基甲基硫酸酯，其摩尔或质量比取决于反应条件，特别是仅从甜菜碱或大蒜素中或两者的混合物中合成。还提供了治疗甲氧西林耐药金黄色葡萄球菌的方法。还提供了一个工具包，其中包括第一容器中的甜菜碱和第二容器中的大蒜素。
• US9707201B2
  申请人：——

  公开号：US9707201B2

  公开（公告）日：2017-07-18
• A Tissue Homogenate Method To Prepare Gram-Scale Allium Thiosulfinates and Their Disulfide Conjugates with Cysteine and Glutathione
  作者：Guodong Zhang、Kirk L. Parkin

  DOI：10.1021/jf4003818

  日期：2013.3.27

  The health benefits of Allium vegetables are widely attributed to the enzyme-derived organosulfur compounds called thiosulfinates (TS). However, the lack of a suitable method to prepare TS in good yields has hampered the evaluation of their biological activities. This paper describe a simple enzymatic method using Allium tissue homogenates as a reaction system to prepare gram-scale TS, including those enriched in 1-propenyl groups, which are particularly difficult to obtain. This method is simple, easy to scale up, and requires no column purification step, making it suitable for practical large-scale production of Allium TS. The prepared TS were further utilized to prepare the disulfide conjugates with cysteine and glutathione (CySSR and GSSR, R = methyl, ethyl, propyl, 1-propenyl, and allyl), which are the presumptive metabolites of TS. Among all of the Allium CySSR and GSSR conjugates, the newly prepared glutathione conjugate with 1-propenyl TS, GSSPe, showed the most potent effect to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7).