2-aminoethaneselenol | 21681-94-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-aminoethaneselenol
• 英文别名: selenocysteamine；2-Amino-ethanselenol; Selenocysteamin；Selenocysteamin
• CAS: 21681-94-7
• 化学式: C₂H₇NSe
• 分子量: 124.044
• InChiKey: KBFHKFAUJGEUJT-UHFFFAOYSA-N

物化性质

• 沸点：
  254.2±32.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.74
• 重原子数：
  4
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-aminoethaneselenol 、 sodium glyoxylate 以61%的产率得到
  参考文献：
  名称：

  MARCO C. DE; CINI C.; COCCIA R.; BLARZINO C., ITAL. J. BIOCHEM., 1979, 28, NO 2, 104-110

  摘要：

  DOI：
• 作为产物：
  描述：

  硒代胱胺 在 sodium tetrahydroborate 作用下， 生成 2-aminoethaneselenol
  参考文献：
  名称：

  The Synthesis of Aminoethyl-Substituted Selenium Compounds

  摘要：

  DOI：

  10.1021/jo01018a504

文献信息

• 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.
• Selenols catalyze the interchange reactions of dithiols and disulfides in water
  作者：Rajeeva Singh、George M. Whitesides

  DOI：10.1021/jo00024a041

  日期：1991.11
• Selenium and Sulfur in Exchange Reactions: A Comparative Study
  作者：Daniel Steinmann、Thomas Nauser、Willem H. Koppenol

  DOI：10.1021/jo1011569

  日期：2010.10.1

  Cysteamine reduces selenocystamine to form hemiselenocystamine and then cystamine. The rate constants are k(1) = 1.3 x 10(5) M-1 s(-1); k(-1) = 2.6 x 10(7) M-1 s(-1); k(2) = 11 M-1 s(-1); and k(-2) = 1.4 x 10(3) M-1 s(-1), respectively. Rate constants for reactions of cysteine/selenocystine are similar. Reaction rates of selenium as a nucleophile and as an electrophile are 2-3 and 4 orders of magnitude higher, respectively, than those of sulfur. Sulfides and selenides are comparable as leaving groups.
• Methyltransferase-Directed Derivatization of 5-Hydroxymethylcytosine in DNA
  作者：Zita Liutkevičiūtė、Edita Kriukienė、Indrė Grigaitytė、Viktoras Masevičius、Saulius Klimašauskas

  DOI：10.1002/anie.201007169

  日期：2011.2.25

  Cytosine modification by AdoMet–dependent DNA methyltransferases is part of an epigenetic regulatory network in vertebrates. Here we show that, in the absence of AdoMet, bacterial cytosine-5 methyltransferases can catalyze condensation of aliphatic thiols and selenols to 5-hydroxymethylcytosine in DNA yielding 5-chalcogenomethyl derivatives. These new atypical reactions open new ways for sequence-specific derivatization and analysis of 5-hydroxymethylcytosine, a recently discovered nucleobase in mammalian DNA
• A comparative study of the kinetics of selenol/diselenide and thiol/disulfide exchange reactions
  作者：Joan C. Pleasants、Wei Guo、Dallas L. Rabenstein

  DOI：10.1021/ja00199a012

  日期：1989.8