(2R)-2-氨基-3-甲基二硫基丙酸 | 33784-54-2

• 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: (2R)-2-氨基-3-甲基二硫基丙酸
• 英文名称: S-(methylthio)-L-cysteine
• 英文别名: S-methylmercapto-L-cysteine；S-(Methylmercapto)cystein；S-Methylthiocysteine；(2R)-2-amino-3-(methyldisulfanyl)propanoic acid
• CAS: 33784-54-2
• 化学式: C₄H₉NO₂S₂
• 分子量: 167.253
• InChiKey: PYFNLWPQPNXHCS-VKHMYHEASA-N

物化性质

• 熔点：
  205-206 °C
• 沸点：
  309.6±37.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2930909090

反应信息

• 作为产物：
  描述：

  氯硫基甲烷 、 L-半胱氨酸盐酸盐无水物 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 以69%的产率得到(2R)-2-氨基-3-甲基二硫基丙酸
  参考文献：
  名称：

  保护基团在以半胱氨酸为模型制备锝-99 m 硫醇盐配合物中的作用

  摘要：

  已经尝试为具有这种功能的 99mTc 结合配体的硫醇盐功能开发合适的保护基团，并且可以在 99mTc 螯合期间自动脱保护，而无需使用任何额外的试剂。选择像 L-半胱氨酸这样的简单分子作为模型配体。合成了该氨基酸的七个 S 保护衍生物，在各种实验条件下用锝 99 m 进行放射性标记，并通过 HPLC 将所需螯合物的产率与 99mTc-L-半胱氨酸（真正的标准螯合物）的产率进行比较。还制备了来自L-胱氨酸和S-硫甲基L-半胱氨酸的相应半胱氨酸的99Tc螯合物。发现 99Tc 螯合物在反相 HPLC 中表现出与相应 99mTc 螯合物相似的保留曲线。99mTc 螯合后的生物分布研究结果同样与 99mTc-L-半胱氨酸的结果进行比较。丙磺舒对肾排泄的影响仅在 S-硫代甲基-L-半胱氨酸的 99mTc 螯合物上进行研究，以确定是否涉及肾小管排泄。结果表明，S-硫代甲基可用作理想的保护基团，以掩盖与不同

  DOI：

  10.1002/jlcr.1084

文献信息

• PdCl₂/DMSO-Catalyzed Thiol–Disulfide Exchange: Synthesis of Unsymmetrical Disulfide
  作者：Jimin Guo、Jianjian Zha、Tao Zhang、Chang-Hua Ding、Qitao Tan、Bin Xu

  DOI：10.1021/acs.orglett.1c00858

  日期：2021.4.16

  Unsymmetrical disulfides have been effectively prepared through thiol exchange with symmetrical disulfides employing a simple PdCl2/DMSO catalytic system. The given method features excellent functional group tolerance, a broad substrate scope, and operational simplicity. This reaction is especially useful for late-stage functionalization of bioactive scaffolds such as peptides and pharmaceuticals.

  通过使用简单的PdCl 2 / DMSO催化系统与对称的二硫化物进行硫醇交换，可以有效地制备不对称的二硫化物。给定的方法具有出色的官能团耐受性，广泛的底物范围和操作简便性。该反应对于诸如肽和药物之类的生物活性支架的后期功能化特别有用。还已经制备了含二硫化物的有机染料。这种转化可以扩展到硫醇-二硒化物或硫醇-二碲化物交换，从而提供RS-SeR'或RS-TeR'。
• Characterisation of the<scp>l</scp>-Cystine β-Lyase PatB from<i>Phaeobacter inhibens</i>: An Enzyme Involved in the Biosynthesis of the Marine Antibiotic Tropodithietic Acid
  作者：Jeroen S. Dickschat、Jan Rinkel、Tim Klapschinski、Jörn Petersen

  DOI：10.1002/cbic.201700358

  日期：2017.11.16

  β‐lyase from P. inhibens is biochemically characterised in terms of the identification of products from the natural substrate, its substrate scope and enzyme kinetics, and by site‐directed mutagenesis. The obtained results, together with feeding experiments with 34S‐labelled substrates, corroborate a previously suggested mechanism for sulfur incorporation into the antibiotic tropodithietic acid.

  黏附在硫中：来自Inhibens的l-胱氨酸β-裂合酶的生化特征在于可鉴定天然底物的产物，其底物范围和酶动力学，以及通过定点诱变。获得的结果，再加上用34 S标记底物进行的进料实验，证实了以前提出的将硫掺入抗生素对二硫代乙酸的机理。
• 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).
• Yurugi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 514,517
  作者：Yurugi

  DOI：——

  日期：——
• Cysteine and Glutathione Mixed-Disulfide Conjugates of Thiosulfinates: Chemical Synthesis and Biological Activities
  作者：Guodong Zhang、Bin Li、Chen-Hsien Lee、Kirk L. Parkin

  DOI：10.1021/jf9029354

  日期：2010.2.10

  The chemical syntheses of cysteine (CYS) and glutathione (GSH) mixed -disulfide conjugates (CySSR, GSSR, respectively) of mercapto residues representing most of the R groups of thiosulfinates (R = methyl, ethyl, propyl, and allyl) are described. Gram-scale conjugates were prepared as >98% pure preparations, with 80% reaction yield for each of the two seminal synthesis steps, with structures confirmed by H-1 NMR and high-resolution MS analyses. These conjugates are derivatives of thiosulfinates that may be evolved in processed foods, in the digestive tract, and through in vivo metabolism. The prepared conjugates were found to be able to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7), indicating they have potential cancer preventive and anti-inflammatory activities. Among the prepared conjugates, the allyl conjugates of CYS and GSH, S-allylmercaptocysteine (CySSA) and S-allylmercaptoglutathione (GSSA), showed the most potent activity regarding QR induction and NO production inhibition. The conjugates with saturated R groups were also active and conferred biological activity as cystine and oxidized glutathione exhibited no effects in these cellular assays.