(2R)-2-amino-3-selanylpropanoate | 1148111-64-1

• 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: (2R)-2-amino-3-selanylpropanoate
• CAS: 1148111-64-1
• 化学式: C₃H₆NO₂Se
• 分子量: 167.046
• InChiKey: ZKZBPNGNEQAJSX-REOHCLBHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.62
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-胱氨酸 、 (2R)-2-amino-3-selanylpropanoate 生成 hemiselenocystine
  参考文献：
  名称：

  Selenium and Sulfur in Exchange Reactions: A Comparative Study

  摘要：

  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.

  DOI：

  10.1021/jo1011569
• 作为产物：
  描述：

  L-硒代胱胺基乙酸 在 sodium hydroxide 、 1,4-二巯基-2,3-丁二醇 作用下， 以 water-d2 为溶剂， 生成 (2R)-2-amino-3-selanylpropanoate
  参考文献：
  名称：

  Role of Substrate Reactivity in the Glutathione Peroxidase (GPx) Activity of Selenocystine

  摘要：

  硒半胱氨酸（CysSeSeCys）是一种双硒化合物，表现出谷胱甘肽过氧化物酶（GPx）活性，它催化使用硫醇辅因子的过氧化氢还原反应。为了理解两种底物的相对反应性，采用Dalziel动力学法在氢过氧化物（H2O2）、t-丁基过氧化物或α-茴香醇过氧化物以及谷胱甘肽或二硫苏糖醇（DTTred）的存在下，确定了酶动力学参数，即转化数（kcat）以及对硫醇（φG）和过氧化氢（φH）的相对反应性参数。通过77Se NMR光谱对CysSeSeCys与H2O2和DTTred反应过程中形成的中间体进行了表征。HF/6-31G(d)的从头计算表明，与H2O2的反应是放热的，而与DTTred的反应是吸热的。基于这些研究，CysSeSeCys的GPx活性可能是通过与过氧化氢的反应启动的，在催化循环中，硫醇的反应是速率决定环节。

  DOI：

  10.1246/bcsj.20090348

文献信息

• Correlating the GPx Activity of Selenocystine Derivatives with One-Electron Redox Reactions
  作者：Beena Mishra、Atanu Barik、Amit Kunwar、Liladhar B. Kumbhare、K. Indira Priyadarsini、Vimal K. Jain

  DOI：10.1080/10426500801901046

  日期：2008.4.1

  With an aim to develop water soluble, less toxic glutathione peroxidase (GPx) mimics, three selenocystine (SeCys) derivatives, viz., selenocystamine (SeA), diselenodipropionic acid (SeP), and methyl ester of diselenodipropionic acid (MeSeP) have been synthesized and examined for GPx activity along with SeCys. The GPx activity of the compounds was found to be in the order SeCys congruent to SeA > MeSeP > SeP. The relative affinity of these GPx mimics towards the substrates thiol and hydroperoxide were determined by Lineweaver-Burk (L-B) plots. Since the enzyme activity involves several steps of reduction and oxidation reactions, attempts have been made to understand the role of such processes in deciding the efficacy of diselenides as GPx mimics. For this, one-electron redox chemistry of these compounds was studied in aqueous solutions at pH 7 using nanosecond pulse radiolysis technique. From these studies, it was concluded that SeCys and SeA, which can undergo easy one-electron reduction, exhibit high GPx activity.
• Role of Substrate Reactivity in the Glutathione Peroxidase (GPx) Activity of Selenocystine
  作者：Beena G. Singh、Partha P. Bag、Fumio Kumakura、Michio Iwaoka、K. Indira. Priyadarsini

  DOI：10.1246/bcsj.20090348

  日期：2010.6.15

  Selenocystine (CysSeSeCys), a diselenide, exhibits glutathione peroxidase (GPx) activity, where it catalyses the reduction of hydroperoxides using a thiol co-factor. To understand the relative reactivity of the two substrates, enzyme kinetic parameters, i.e., the turnover number (kcat) and the relative reactivity parameters toward thiol (φG) and hydroperoxide (φH), were determined by applying Dalziel kinetics for a bi-substrate model in the presence of hydrogen peroxide (H2O2), t-butyl hydroperoxide, or α-cumyl hydroperoxide and glutathione or dithiothreitol (DTTred). The intermediates formed during the reaction of CysSeSeCys with H2O2 and DTTred were characterized by 77Se NMR spectroscopy. Ab initio calculation at HF/6-31G(d) indicated that the reactions with H2O2 are exothermic, while those with DTTred are endothermic. Based on these studies, the GPx activity of CysSeSeCys is likely to be initiated by the reaction with hydroperoxide and in the catalytic cycle, the reaction with thiol is the rate-determining step.

  硒半胱氨酸（CysSeSeCys）是一种双硒化合物，表现出谷胱甘肽过氧化物酶（GPx）活性，它催化使用硫醇辅因子的过氧化氢还原反应。为了理解两种底物的相对反应性，采用Dalziel动力学法在氢过氧化物（H2O2）、t-丁基过氧化物或α-茴香醇过氧化物以及谷胱甘肽或二硫苏糖醇（DTTred）的存在下，确定了酶动力学参数，即转化数（kcat）以及对硫醇（φG）和过氧化氢（φH）的相对反应性参数。通过77Se NMR光谱对CysSeSeCys与H2O2和DTTred反应过程中形成的中间体进行了表征。HF/6-31G(d)的从头计算表明，与H2O2的反应是放热的，而与DTTred的反应是吸热的。基于这些研究，CysSeSeCys的GPx活性可能是通过与过氧化氢的反应启动的，在催化循环中，硫醇的反应是速率决定环节。
• 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.