3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate | 1238388-56-1

• 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: 3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate
• 英文别名: selenoneine；2-selenyl-Nα,Nα,Nα-trimethyl-L-histidine；5-[(2S)-2-carboxy-2-(trimethylazaniumyl)ethyl]-1H-imidazole-2-selenolate
• CAS: 1238388-56-1
• 化学式: C₉H₁₅N₃O₂Se
• 分子量: 276.197
• InChiKey: MTIQLELFQVCRSW-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.09
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 selenoneine dimer
  参考文献：
  名称：

  Identification of a Novel Selenium-containing Compound, Selenoneine, as the Predominant Chemical Form of Organic Selenium in the Blood of Bluefin Tuna

  摘要：

  A novel selenium-containing compound having a selenium atom in the imidazole ring, 2-selenyl-N-alpha,N-alpha,N-alpha-trimethyl-L-histidine, 3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate, was identified from the blood and other tissues of the bluefin tuna, Thunnus orientalis. The seleniumcontaining compound was purified from the tuna blood in several chromatographic steps. High resolution mass spectrometry and nuclear magnetic resonance spectroscopy showed that the exact mass of the [M + H](+) ion of the compound was 533.0562 and the molecular formula was C18H29N6O4Se2. Its gross structure was assigned as the oxidized dimeric form of an ergothioneine selenium analog in which the sulfur of ergothioneine is replaced by selenium. Therefore, we named this novel seleniumcontaining compound "selenoneine." By speciation analysis of organic selenium compounds using liquid chromatography inductively coupled plasma mass spectrometry, selenoneine was found widely distributed in various tissues of the tuna, with the highest concentration in blood; mackerel blood contained similar levels. Selenoneine was measurable at 2-4 orders of magnitude lower concentration in a limited set of tissues from squid, tilapia, pig, and chicken. Quantitatively, selenoneine is the predominant form of organic selenium in tuna tissues.

  DOI：

  10.1074/jbc.c110.106377
• 作为产物：
  描述：

  selenoneine dimer 在 Cleland's reagent 作用下， 以 水 为溶剂， 反应 0.5h， 生成 3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate
  参考文献：
  名称：

  Identification of a Novel Selenium-containing Compound, Selenoneine, as the Predominant Chemical Form of Organic Selenium in the Blood of Bluefin Tuna

  摘要：

  A novel selenium-containing compound having a selenium atom in the imidazole ring, 2-selenyl-N-alpha,N-alpha,N-alpha-trimethyl-L-histidine, 3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate, was identified from the blood and other tissues of the bluefin tuna, Thunnus orientalis. The seleniumcontaining compound was purified from the tuna blood in several chromatographic steps. High resolution mass spectrometry and nuclear magnetic resonance spectroscopy showed that the exact mass of the [M + H](+) ion of the compound was 533.0562 and the molecular formula was C18H29N6O4Se2. Its gross structure was assigned as the oxidized dimeric form of an ergothioneine selenium analog in which the sulfur of ergothioneine is replaced by selenium. Therefore, we named this novel seleniumcontaining compound "selenoneine." By speciation analysis of organic selenium compounds using liquid chromatography inductively coupled plasma mass spectrometry, selenoneine was found widely distributed in various tissues of the tuna, with the highest concentration in blood; mackerel blood contained similar levels. Selenoneine was measurable at 2-4 orders of magnitude lower concentration in a limited set of tissues from squid, tilapia, pig, and chicken. Quantitatively, selenoneine is the predominant form of organic selenium in tuna tissues.

  DOI：

  10.1074/jbc.c110.106377

文献信息

• Genetic and Metabolomic Dissection of the Ergothioneine and Selenoneine Biosynthetic Pathway in the Fission Yeast, S. pombe, and Construction of an Overproduction System
  作者：Tomáš Pluskal、Masaru Ueno、Mitsuhiro Yanagida

  DOI：10.1371/journal.pone.0097774

  日期：——

  metabolomic analysis, that the Δegt1 deletion mutant completely lacked ergothioneine and its precursors (trimethyl histidine/hercynine and hercynylcysteine sulfoxide). Since the second step of ergothioneine biosynthesis has not been characterized in eukaryotes, we examined four putative homologs (Nfs1/SPBC21D10.11c, SPAC11D3.10, SPCC777.03c, and SPBC660.12c) of the corresponding mycobacterial enzyme

  麦角硫因是由各种细菌和真菌合成的一种小的含硫代谢物 (229 Da)，可在高等真核生物的组织或细胞（例如红细胞）中积累至毫摩尔水平。由于其提出的保护和抗氧化功能，它通常作为膳食补充剂销售。在这项研究中，我们报告了在裂殖酵母粟酒裂殖酵母中形成两步麦角硫因生物合成途径的基因。我们通过与先前发表的粗糙脉孢菌和耻垢分枝杆菌基因的序列同源性鉴定了第一个基因 egt1+ (SPBC1604.01)。我们使用代谢组学分析表明，Δegt1 缺失突变体完全缺乏麦角硫因及其前体（三甲基组氨酸/海西氨酸和海西半胱氨酸亚砜）。由于麦角硫因生物合成的第二步尚未在真核生物中表征，因此我们检测了相应分枝杆菌酶 EgtE 的四种推定同源物（Nfs1/SPBC21D10.11c、SPAC11D3.10、SPCC777.03c 和 SPBC660.12c）。在这些基因的缺失突变体中，只有一个（ΔSPBC660.12c，指定为
• WO2023/155006
  申请人：——

  公开号：——

  公开（公告）日：——