methyl (2R)-2-acetamido-3-(1,3-benzothiazol-2-yldisulfanyl)propanoate | 1262406-54-1

• 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: methyl (2R)-2-acetamido-3-(1,3-benzothiazol-2-yldisulfanyl)propanoate
• CAS: 1262406-54-1
• 化学式: C₁₃H₁₄N₂O₃S₃
• 分子量: 342.464
• InChiKey: FFBUCBRZDJFQLF-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-acetamido-3-(1,3-benzothiazol-2-yldisulfanyl)propanoate 、 氰乙酸甲酯 以 四氢呋喃 、 aq. phosphate buffer 为溶剂， 反应 0.33h， 以93%的产率得到methyl (2S)-2-acetamido-3-(1-cyano-2-methoxy-2-oxoethyl)sulfanylpropanoate
  参考文献：
  名称：

  Detection of Protein S-Sulfhydration by a Tag-Switch Technique

  摘要：

  AbstractProtein S‐sulfhydration (forming ‐S‐SH adducts from cysteine residues) is a newly defined oxidative posttranslational modification and plays an important role in H2S‐mediated signaling pathways. In this study we report the first selective, “tag‐switch” method which can directly label protein S‐sulfhydrated residues by forming stable thioether conjugates. Furthermore we demonstrate that H2S alone cannot lead to S‐sulfhydration and that the two possible physiological mechanisms include reaction with protein sulfenic acids (P‐SOH) or the involvement of metal centers which would facilitate the oxidation of H2S to HS..

  DOI：

  10.1002/anie.201305876
• 作为产物：
  描述：

  (R)-methyl 2-acetamido-3-(nitrosothio)propanoate 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 methyl (2R)-2-acetamido-3-(1,3-benzothiazol-2-yldisulfanyl)propanoate
  参考文献：
  名称：

  Disulfide formation via sulfenamides

  摘要：

  我们开发了一种由磷化氢介导的一步法 S-亚硝硫醇二硫化物形成反应。该反应可在非常温和的条件下将不稳定的 S-亚硝硫醇转化为稳定的二硫化物-亚硫酰胺中间体。它具有用于检测 S-亚硝硫醇的潜力。

  DOI：

  10.1039/c0cc02076a

文献信息

• DETECTION OF PROTEIN S-SULFHYDRATION VIA A TAG-SWITCH TECHNIQUE
  申请人：Washington State University

  公开号：US20150099305A1

  公开（公告）日：2015-04-09

  Methods and assays for detecting S-sulfhydration of amino acids in proteins, polypeptides and peptides are provided. The method is a two-step “tag-switch” method employing two reagents consecutively to specifically label, with a detectable label, persulfide (—S—SH) linkages in proteins, polypeptides and peptides.
• US9453844B2
  申请人：——

  公开号：US9453844B2

  公开（公告）日：2016-09-27
• Detection of Protein S-Sulfhydration by a Tag-Switch Technique
  作者：Dehui Zhang、Igor Macinkovic、Nelmi O. Devarie-Baez、Jia Pan、Chung-Min Park、Kate S. Carroll、Milos R. Filipovic、Ming Xian

  DOI：10.1002/anie.201305876

  日期：2014.1.7

  AbstractProtein S‐sulfhydration (forming ‐S‐SH adducts from cysteine residues) is a newly defined oxidative posttranslational modification and plays an important role in H2S‐mediated signaling pathways. In this study we report the first selective, “tag‐switch” method which can directly label protein S‐sulfhydrated residues by forming stable thioether conjugates. Furthermore we demonstrate that H2S alone cannot lead to S‐sulfhydration and that the two possible physiological mechanisms include reaction with protein sulfenic acids (P‐SOH) or the involvement of metal centers which would facilitate the oxidation of H2S to HS..
• Disulfide formation via sulfenamides
  作者：Jia Pan、Ming Xian

  DOI：10.1039/c0cc02076a

  日期：——

  A phosphine-mediated one-step disulfide formation from S-nitrosothiols has been developed. This reaction can convert unstable S-nitrosothiols to stable disulfidesviasulfenamide intermediates under very mild conditions. It has the potential to be used for the detection ofS-nitrosothiols.

  我们开发了一种由磷化氢介导的一步法 S-亚硝硫醇二硫化物形成反应。该反应可在非常温和的条件下将不稳定的 S-亚硝硫醇转化为稳定的二硫化物-亚硫酰胺中间体。它具有用于检测 S-亚硝硫醇的潜力。