selenocystine dimethyl ester | 739301-12-3

• 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: selenocystine dimethyl ester
• 英文别名: methyl (2R)-2-amino-3-[[(2R)-2-amino-3-methoxy-3-oxopropyl]diselanyl]propanoate
• CAS: 739301-12-3
• 化学式: C₈H₁₆N₂O₄Se₂
• 分子量: 362.146
• InChiKey: GUIIRGADLZRAGD-WDSKDSINSA-N

物化性质

• 沸点：
  432.9±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.85
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  selenocystine dimethyl ester 在 sodium tetrahydroborate 作用下， 生成 selenocysteine methyl ester
  参考文献：
  名称：

  Kinetics of reaction of peroxynitrite with selenium- and sulfur-containing compounds: Absolute rate constants and assessment of biological significance

  摘要：

  Peroxynitrite (the physiological mixture of ONOOH and its anion, ONOO-) is a powerful biologically-relevant oxidant capable of oxidizing and damaging a range of important targets including sulfides, thiols, lipids, proteins, carbohydrates and nucleic acids. Excessive production of peroxynitrite is associated with several human pathologies including cardiovascular disease, ischemic-reperfusion injury, circulatory shock, inflammation and neurodegeneration. This study demonstrates that low-molecularmass selenols (RSeH), selenides (RSeR') and to a lesser extent diselenides (RSeSeR') react with peroxynitrite with high rate constants. Low molecular mass selenols react particularly rapidly with peroxynitrite, with second order rate constants k(2) in the range 5.1 x 10(5)-1.9 x 10(6) M-1 s(-1), and 250-830 fold faster than the corresponding thiols (RSH) and many other endogenous biological targets. Reactions of peroxynitrite with selenides, including selenosugars are approximately 15-fold faster than their sulfur homologs with k(2) approximately 2.5 x 10(3) M-1 s(-1). The rate constants for diselenides and sulfides were slower with k(2) 0.72-1.3 x 10(3) M-1 s(-1) and approximately 2.1 x 10(2) M-1 s(-1) respectively. These studies demonstrate that both endogenous and exogenous selenium-containing compounds may modulate peroxynitrite-mediated damage at sites of acute and chronic inflammation, with this being of particular relevance at extracellular sites where the thiol pool is limited. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2015.10.424
• 作为产物：
  描述：

  N-Boc-L-硒代胱氨酸甲酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 selenocystine dimethyl ester
  参考文献：
  名称：

  SLAP试剂，用于光催化合成C3 / C5取代的N-未保护的硒代吗啉和1,4-硒代庚烷。

  摘要：

  在这里，我们公开了第一组独特的含硒SLAP（硅胺协议）试剂，用于在温和的光催化条件下，由多种（杂）醛直接合成C3 / C5取代的硒代吗啉和1,4-硒代庚烷。还合成了这些杂环的对映体纯的1,2-氨基醇/α-氨基酸。此外，我们已经显示了使用开发的硒代SLAP试剂对某些生物活性剂的后期修饰。

  DOI：

  10.1039/d0cc04471g

文献信息

• Selenols are resistant to irreversible modification by HNO
  作者：Christopher L. Bianco、Cathy D. Moore、Jon M. Fukuto、John P. Toscano

  DOI：10.1016/j.freeradbiomed.2016.07.008

  日期：2016.10

  to be additional potential targets of HNO. Indeed, as determined in the current work, selenols are targeted by HNO. Such reactions appear to result only in formation of diselenide products, which can be easily reverted back to the free selenol. This characteristic is distinct from the reaction of HNO with thiols/thiolproteins. These findings suggest that, unlike thiolproteins, selenoproteins are resistant

  一氧化氮（NO）作为哺乳动物细胞内源性产生的信号传导物种的发现，引起了对氮氧化物化学生物学研究的巨大兴趣。其中，硝酰氧基（氮杂酮，HNO）作为心血管疾病的治疗剂具有潜在的作用。HNO的已知靶标包括血红素/血红素蛋白和含硫醇/含硫醇的蛋白。最近，由于它们在氧化还原信号传导和细胞防御中的作用，硒醇和硒蛋白也被认为是HNO的其他潜在靶标。确实，如当前工作所确定，硒醇是HNO的目标。这样的反应似乎仅导致二硒化物产物的形成，其可以容易地还原成游离硒醇。该特征不同于HNO与硫醇/硫醇蛋白的反应。
• Stocking, Emily M.; Schwarz, Jessie N.; Senn, Hans, Journal of the Chemical Society. Perkin transactions I, 1997, # 16, p. 2443 - 2447
  作者：Stocking, Emily M.、Schwarz, Jessie N.、Senn, Hans、Salzmann, Michael、Silks, Louis A.

  DOI：——

  日期：——
• Kinetics of reaction of peroxynitrite with selenium- and sulfur-containing compounds: Absolute rate constants and assessment of biological significance
  作者：Corin Storkey、David I. Pattison、Marta T. Ignasiak、Carl H. Schiesser、Michael J. Davies

  DOI：10.1016/j.freeradbiomed.2015.10.424

  日期：2015.12

  Peroxynitrite (the physiological mixture of ONOOH and its anion, ONOO-) is a powerful biologically-relevant oxidant capable of oxidizing and damaging a range of important targets including sulfides, thiols, lipids, proteins, carbohydrates and nucleic acids. Excessive production of peroxynitrite is associated with several human pathologies including cardiovascular disease, ischemic-reperfusion injury, circulatory shock, inflammation and neurodegeneration. This study demonstrates that low-molecularmass selenols (RSeH), selenides (RSeR') and to a lesser extent diselenides (RSeSeR') react with peroxynitrite with high rate constants. Low molecular mass selenols react particularly rapidly with peroxynitrite, with second order rate constants k(2) in the range 5.1 x 10(5)-1.9 x 10(6) M-1 s(-1), and 250-830 fold faster than the corresponding thiols (RSH) and many other endogenous biological targets. Reactions of peroxynitrite with selenides, including selenosugars are approximately 15-fold faster than their sulfur homologs with k(2) approximately 2.5 x 10(3) M-1 s(-1). The rate constants for diselenides and sulfides were slower with k(2) 0.72-1.3 x 10(3) M-1 s(-1) and approximately 2.1 x 10(2) M-1 s(-1) respectively. These studies demonstrate that both endogenous and exogenous selenium-containing compounds may modulate peroxynitrite-mediated damage at sites of acute and chronic inflammation, with this being of particular relevance at extracellular sites where the thiol pool is limited. (C) 2015 Elsevier Inc. All rights reserved.
• SLAP reagents for the photocatalytic synthesis of C3/C5-substituted, N-unprotected selenomorpholines and 1,4-selenazepanes
  作者：Guan Zhou、Xingwang Deng、Chenyu Pan、Eunice Tze Leng Goh、Rajamani Lakshminarayanan、Rajavel Srinivasan

  DOI：10.1039/d0cc04471g

  日期：——

  Herein, we disclose the first set of unique selenium-containing SLAP (SiLicon Amine Protocol) reagents for the direct synthesis of C3/C5-substituted selenomorpholines and 1,4-selenazepanes from diverse (hetero)aldehydes under mild photocatalytic conditions. Enantiomerically pure 1,2-amino alcohol/α-amino acid versions of these heterocycles were also synthesized. Further, we have shown the late-stage

  在这里，我们公开了第一组独特的含硒SLAP（硅胺协议）试剂，用于在温和的光催化条件下，由多种（杂）醛直接合成C3 / C5取代的硒代吗啉和1,4-硒代庚烷。还合成了这些杂环的对映体纯的1,2-氨基醇/α-氨基酸。此外，我们已经显示了使用开发的硒代SLAP试剂对某些生物活性剂的后期修饰。