S-methylcysteine sulfoxide | 3226-62-8

• 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: S-methylcysteine sulfoxide
• 英文别名: methionine sulfoxide；methiin；MCSO；(RS)-2-amino-3-(Ξ)-methanesulfinyl-propionic acid；3-(Ξ)-methanesulfinyl-DL-alanine；S-Methyl-L-cystein-SR-sulfoxid；2-Azaniumyl-3-methylsulfinylpropanoate
• CAS: 3226-62-8；4740-94-7；6853-87-8；23315-24-4；32726-14-0；56816-70-7
• 化学式: C₄H₉NO₃S
• 分子量: 151.186
• InChiKey: ZZLHPCSGGOGHFW-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  163°C

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  S-methylcysteine sulfoxide 在 water extract of garlic 作用下， 以 水 为溶剂， 以42%的产率得到甲基甲烷硫代亚磺酸酯
  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
• 作为产物：
  描述：

  S-甲基-半胱氨酸 在 二氧化氯 作用下， 以 水 为溶剂， 反应 1.0h， 以97%的产率得到S-methylcysteine sulfoxide
  参考文献：
  名称：

  Oxidation by chlorine dioxide of methionine and cysteine derivatives to sulfoxides

  摘要：

  甲硫氨酸和半胱氨酸衍生物被二氧化氯不对称氧化为亚磺酰衍生物。

  DOI：

  10.1007/s10600-009-9182-8
• 作为试剂：
  描述：

  S-甲基-L-半胱氨酸 、 双氧水 在 Acetone Acetic Acid H2O 、 S-methylcysteine sulfoxide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 S-methylcysteine sulfoxide
  参考文献：
  名称：

  IMPROVEMENTS IN OR RELATING TO ALLIUM EXTRACTS

  摘要：

  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。

  公开号：

  US20160151324A1

文献信息

• Oxidation reaction of amino acids in aqueous solution induced by argon arc plasma
  作者：Kaoru Harada、Michiaki Takasaki

  DOI：10.1016/s0040-4039(00)94021-8

  日期：1983.1

  It was found that Argon arc plasma induced a powerful and clean stepwise oxidation reaction in aqueous solution containing various amino acids without using any oxidizing agent.

  发现在不使用任何氧化剂的情况下，氩弧等离子体在包含多种氨基酸的水溶液中诱导了强大且清洁的逐步氧化反应。
• YAMADA, XIDEHAKI;KUMAGAI, XIDEHXIKO;OKISI, XARUYUKI
  作者：YAMADA, XIDEHAKI、KUMAGAI, XIDEHXIKO、OKISI, XARUYUKI

  DOI：——

  日期：——
• LARSEN, PEDER OLESEN;SUNDANL, MARIA;SZHUSTORENSEN, FINN TORVEN;WIESZORKOW+, BIOCHEM. SYST. AND ECOL., 15,(1987) N 5, 575-579
  作者：LARSEN, PEDER OLESEN、SUNDANL, MARIA、SZHUSTORENSEN, FINN TORVEN、WIESZORKOW+

  DOI：——

  日期：——
• 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).
• Oxidation by chlorine dioxide of methionine and cysteine derivatives to sulfoxides
  作者：I. V. Loginova、S. A. Rubtsova、A. V. Kuchin

  DOI：10.1007/s10600-009-9182-8

  日期：2008.11

  Methionine and cysteine derivatives were oxidized asymmetrically by chlorine dioxide to sulfinyl derivatives.

  甲硫氨酸和半胱氨酸衍生物被二氧化氯不对称氧化为亚磺酰衍生物。