hercynine | 507-29-9

• 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: hercynine
• 英文别名: Herzynin；Hercymin；3-(1H-imidazol-5-yl)-2-(trimethylazaniumyl)propanoate
• CAS: 507-29-9
• 化学式: C₉H₁₅N₃O₂
• 分子量: 197.237
• InChiKey: GPPYTCRVKHULJH-UHFFFAOYSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  237-238°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  hercynine 在 calcium hypochlorite 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  基于化学衍生氧化产物海西宁和进一步分解产物的麦角硫因抗氧化机制。

  摘要：

  麦角硫因 (ERGO) 是一种硫代组氨酸甜菜碱，存在于各种真菌、植物和动物中。人类从饮食中摄取 ERGO。ERGO 是一种强生物抗氧化剂，但关于其氧化还原机制的报道数量有限。本研究的目的是阐明 ERGO 的氧化机制。进行 ERGO 与化学氧化剂的反应。ERGO 的氧化产物通过核磁共振和液相色谱-质谱 (LC-MS) 进行分析。在生理条件下过氧化氢氧化 ERGO 的主要产物被鉴定为海西宁（组氨酸甜菜碱）。1 分子 ERGO 能够还原 2 分子过氧化氢。Hercynine 被发现与更有效的氧化剂次氯酸盐反应。LC-MS 检测到一种不稳定的分解产物。因此，

  DOI：

  10.1093/bbb/zbab006
• 作为产物：
  描述：

  3,3'-(2,2'-diselanediylbis(1H-imidazol-5,2-diyl))bis(2-(trimethylammonio)propanoate) 在 DL-dithiothreitol 、 双氧水 作用下， 以 aq. phosphate buffer 为溶剂， 反应 4.08h， 生成 hercynine
  参考文献：
  名称：

  硒烯酮的全合成和功能表征。

  摘要：

  N-α-三甲基2-硒代组氨酸硒酮是天然抗氧化剂麦角硫氨酸的硒同系物。已知硫到硒的取代赋予蛋白质和核酸特殊的活性。相比之下，利用硒特异性化学物质的次生代谢物则很少。因此，硒烯酮提供了一个独特的机会来研究天然有机硒酸酯如何与细胞过程相互作用。在本报告中，我们描述了硒酮和其他2-硒代咪唑的化学合成。有了合成硒代丙氨酸，我们发现了一套将硒代丙氨酸与麦角硫因分开的反应活性，表明这两种化合物可以填补不同的功能壁ni。

  DOI：

  10.1002/anie.201908967

文献信息

• Synthesis of N-methyl urocanates of hydroxyderivatives of isocembrol
  作者：F. A. Valeev、Sh. M. Salikhov、O. Yu. Krasnoslobodtseva、B. T. Sharipov、L. V. Spirikhin、G. A. Tolstikov

  DOI：10.1007/s10600-007-0065-6

  日期：2007.3

  Alcohols were prepared by stereospecific hydroxylation of isocembrol and were esterified into N-methylurocanates, proposed biomimetics of taxol.

  醇类是通过异槲皮素的立体选择性羟基化制备的，并酯化为N-甲基乌洛卡酸酯，这是拟仿生紫杉醇的生物仿制品。
• Ergothioneine production through metabolic engineering
  申请人：Liu Pinghua

  公开号：US10167490B2

  公开（公告）日：2019-01-01

  The present disclosure relates to the production of ergothioneine through either in vitro enzymatic transformations or fermentations using microbials created by metabolic engineering. Also disclosed are transformed cells useful in such methods and ergothioneine produced by such methods. Transformed cells of the disclosure are capable of converting histidine and cysteine or hercynine and cysteine into ergothioneine in greater efficiency than the untransformed wild-type cells.

  本公开涉及通过体外酶转化或利用代谢工程微生物发酵生产麦角硫因。还公开了用于这种方法的转化细胞和用这种方法生产的麦角硫因。与未转化的野生型细胞相比，本发明公开的转化细胞能够以更高的效率将组氨酸和半胱氨酸或 hercynine 和半胱氨酸转化为麦角硫因。
• An uncommon redox behavior sheds light on the cellular antioxidant properties of ergothioneine
  作者：Luigi Servillo、Domenico Castaldo、Rosario Casale、Nunzia D’Onofrio、Alfonso Giovane、Domenico Cautela、Maria Luisa Balestrieri

  DOI：10.1016/j.freeradbiomed.2014.11.017

  日期：2015.2

  Ergothioneine (ESH), an aromatic thiol occurring in the human diet and which accumulates in particular cells, is believed to act as an antioxidant. However, its redox mechanism remains unclear and it does not seem to provide any advantage compared to other antioxidants, such as alkylthiols, which are better reducing agents and generally present in cells at higher levels. Here, we investigated by ESI-MS the products of ESH oxidation produced by neutrophils during oxidative burst and, to further elucidate ESH redox behavior, we also analyzed the oxidation products of the reaction of ESH with hypochlorite in cell-free solutions. Indeed, neutrophils are the main source of hypochlorite in humans. Furthermore, we also tested other biologically relevant oxidants, such as peroxynitrite and hydrogen peroxide. Our results indicate that treatment of human neutrophils with phorbol 12-myristate 13-acetate in the presence of ESH leads to a remarkable production of the sulfonated form (ESO3H), a compound never described before, and hercynine (EH), the desulfurated form of ESH. Similar results were obtained when ESH was subjected to cell-free oxidation in the presence of hypochlorite, as well as hydrogen peroxide or peroxynitrite. Furthermore, when the disulfide of ESH was reacted with those oxidants, we found that it was also oxidized, with production of EH and ESO3H, whose amount was dependent on the oxidant strength. These data reveal a unique ESH redox behavior, entirely different from that of alkylthiols, and suggest a mechanism, so far overlooked, through which ESH performs its antioxidant action in cells. (C) 2015 Published by Elsevier Inc.
• Barger; Ewins, Journal of the Chemical Society, 1911, vol. 99, p. 2340
  作者：Barger、Ewins

  DOI：——

  日期：——
• Engeland; Kutscher, Chemisches Zentralblatt, 1913, vol. 84, # I, p. 28
  作者：Engeland、Kutscher

  DOI：——

  日期：——