(RS)-2-amino-5-mercaptopentanoic acid hydrochloride | 144072-93-5

• 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: (RS)-2-amino-5-mercaptopentanoic acid hydrochloride
• 英文别名: 1-carboxy-4-mercaptobutan-1-aminium chloride；thioornithine hydrochloride；2-amino-5-mercaptopentanoic acid hydrochloride；2-Amino-5-sulfanylpentanoic acid;hydrochloride
• CAS: 144072-93-5
• 化学式: C₅H₁₁NO₂S*ClH
• 分子量: 185.675
• InChiKey: QTHWFMOVTYVRTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.3
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (RS)-2-amino-5-mercaptopentanoic acid hydrochloride 在 盐酸 作用下， 反应 20.0h， 生成 甲基5-硫基-L-去甲缬氨酸酯 、
  参考文献：
  名称：

  Synthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids

  摘要：

  Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to alpha-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H). Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100%). The solvent used for the reaction is critical. Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems). The scope of the reaction includes alpha-substituted alpha-allylglycine and derivatives as well as beta-substituted beta-allyl-beta-ammo alcohols. In the case of optically active alpha-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H. The products are easily optically enriched by crystallization. Addition of sulfur-based radicals to alpha-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.

  DOI：

  10.1021/jo00049a041
• 作为产物：
  描述：

  ethyl 5-(acetylthio)-2-((diphenylmethylene)amino)pentanoate 在 盐酸 作用下， 以 水 为溶剂， 以77 %的产率得到(RS)-2-amino-5-mercaptopentanoic acid hydrochloride
  参考文献：
  名称：

  适合片段筛选的比色测定揭示了奥罗恩和查尔酮作为新的精氨酸酶抑制剂

  摘要：

  精氨酸酶是一种难以靶向的金属酶，与多种疾病有关，包括癌症、传染病和心血管疾病。尽管存在医学需求，但现有抑制剂的结构多样性有限，主要由氨基酸及其衍生物组成。对创新精氨酸酶抑制剂的探索现已扩展到筛选方法。由于精氨酸酶的活性位点小而窄，筛选必须满足基于片段的筛选标准。然而，片段的结合能力有限，需要在高浓度下工作，这增加了干扰和误报的风险。在这项研究中，我们研究了三种比色测定法，并根据干扰选择了一种在这些具有挑战性的条件下进行筛选。随后对金属螯合剂片段库的筛选进行调整和应用，鉴定出四种具有中等活性的化合物。对其中一个热门化合物的一系列化合物进行合成和评估，得到化合物21a ，其 IC 50值为 91.1 μM，接近参考化合物白皮杉醇。最后，分子模型支持金酮和查耳酮与精氨酸酶活性位点的潜在结合，表明它们是开发新型精氨酸酶抑制剂的新候选者。

  DOI：

  10.1039/d3md00713h

文献信息

• Synthesis of Thiol-Containing Amino Acids Through Alkylation of Glycinate Ketimine
  作者：Jian Zhi、Yuli Xiao、Aiguo Hu

  DOI：10.1080/00397911.2010.533803

  日期：2012.3.15

  Abstract A general synthetic route for the synthesis of thiol-containing amino acids through alkylation of glycinate ketimine followed by hydrolysis was developed in this work. The common problems associated with the instability of ketimines and thioesters were solved by optimization of both synthetic and purification conditions. A series of thiol-containing amino acids were obtained in good yields. This method

  摘要 本工作建立了一种通过甘氨酸酮亚胺烷基化和水解合成含硫醇氨基酸的通用合成路线。通过优化合成和纯化条件解决了与酮亚胺和硫酯的不稳定性相关的常见问题。以良好的收率获得了一系列含硫醇的氨基酸。这种方法可以很容易地扩展到其他含硫醇氨基酸的合成，这些氨基酸是药物研究和医学应用中的重要中间体。图形概要
• Synthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids
  作者：Quirinus B. Broxterman、Bernard Kaptein、Johan Kamphuis、Hans E. Schoemaker

  DOI：10.1021/jo00049a041

  日期：1992.11

  Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to alpha-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H). Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100%). The solvent used for the reaction is critical. Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems). The scope of the reaction includes alpha-substituted alpha-allylglycine and derivatives as well as beta-substituted beta-allyl-beta-ammo alcohols. In the case of optically active alpha-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H. The products are easily optically enriched by crystallization. Addition of sulfur-based radicals to alpha-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.
• A colorimetric assay adapted to fragment screening revealing aurones and chalcones as new arginase inhibitors
  作者：Jason Muller、Luca Marchisio、Rym Attia、Andy Zedet、Robin Maradan、Maxence Vallet、Alison Aebischer、Dominique Harakat、François Senejoux、Christophe Ramseyer、Sarah Foley、Bruno Cardey、Corine Girard、Marc Pudlo

  DOI：10.1039/d3md00713h

  日期：——

  However, the limited binding capacity of fragments requires working at high concentrations, which increases the risk of interference and false positives. In this study, we investigated three colorimetric assays and selected one based on interference for screening under these challenging conditions. The subsequent adaptation and application to the screening a library of metal chelator fragments resulted

  精氨酸酶是一种难以靶向的金属酶，与多种疾病有关，包括癌症、传染病和心血管疾病。尽管存在医学需求，但现有抑制剂的结构多样性有限，主要由氨基酸及其衍生物组成。对创新精氨酸酶抑制剂的探索现已扩展到筛选方法。由于精氨酸酶的活性位点小而窄，筛选必须满足基于片段的筛选标准。然而，片段的结合能力有限，需要在高浓度下工作，这增加了干扰和误报的风险。在这项研究中，我们研究了三种比色测定法，并根据干扰选择了一种在这些具有挑战性的条件下进行筛选。随后对金属螯合剂片段库的筛选进行调整和应用，鉴定出四种具有中等活性的化合物。对其中一个热门化合物的一系列化合物进行合成和评估，得到化合物21a ，其 IC 50值为 91.1 μM，接近参考化合物白皮杉醇。最后，分子模型支持金酮和查耳酮与精氨酸酶活性位点的潜在结合，表明它们是开发新型精氨酸酶抑制剂的新候选者。