Ergothionein | 162240-56-4

• 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: Ergothionein
• 英文别名: ergothioneine；5-[2-carboxy-2-(trimethylazaniumyl)ethyl]-1H-imidazole-2-thiolate
• CAS: 162240-56-4
• 化学式: C₉H₁₅N₃O₂S
• 分子量: 229.303
• InChiKey: SSISHJJTAXXQAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 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：
  96.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ergothionein 在 双氧水 作用下， 以 水 为溶剂， 生成 hercynine
  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：

  l-histidine methyl ester dihydrochloride 在 palladium on activated charcoal TEA 、 氢气 、 碳酸氢钠 、 三乙胺 、 硫代氯甲酸苯酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 10.0~60.0 ℃ 、506.62 kPa 条件下， 反应 97.5h， 生成 Ergothionein
  参考文献：
  名称：

  Synthesis of L-(+)-Ergothioneine

  摘要：

  The first synthesis of L-(+)-ergothioneine (1), a rare natural amino acid, is described. The key step is the direct transformation of the imidazole derivative 11 into imidazole-2-thione 12. This reaction consists of the cleavage and the re-formation of imidazole ring (ANRORC) with phenyl chlorothionoformate via a Bamberger-type intermediate. The conditions used are mild enough to preserve the asymmetric center at the a-carbon. The release of enantiomerically pure L-ergothioneine (1) from the ammonium derivative 15 was performed under acidic conditions to avoid the very easy racemization of the betaine function. An efficient and high-yield synthesis of 2-mercapto-L-histidine (2) which uses the new imidazole-2-thione formation reaction is also described.

  DOI：

  10.1021/jo00125a014

文献信息

• NOVEL SELENIUM-CONTAINING COMPOUNDS
  申请人：YAMASHITA Yumiko

  公开号：US20110178018A1

  公开（公告）日：2011-07-21

  A novel selenium-containing compound, a method of producing the selenium-containing compound, an analysis method using the selenium-containing compound, and use of the selenium-containing compound as an antioxidant, are disclosed. A novel selenium-containing compound shown by any of chemical formulas 1 to 4 is obtained by extracting a selenium-containing compound from a sample using an organic solvent or water, and purifying the selenium-containing compound. The novel selenium-containing compound may be used for a novel analysis method, or may be used as an antioxidant.

  揭示了一种新的含硒化合物，生产该含硒化合物的方法，使用该含硒化合物的分析方法，以及将该含硒化合物用作抗氧化剂的用途。通过使用有机溶剂或水从样品中提取含硒化合物，并纯化含硒化合物，可以获得任何化学式1至4所示的一种新的含硒化合物。这种新的含硒化合物可以用于一种新的分析方法，也可以用作抗氧化剂。
• PROCESS FOR THE SYNTHESIS OF L-(+)-ERGOTHIONEINE
  申请人：Trampota Miroslav

  公开号：US20090093642A1

  公开（公告）日：2009-04-09

  This invention relates to a novel process for the preparation of optically pure L-(+)-ergothioneine. The process for the chemical synthesis of L-ergothioneine comprises steps which consist of reacting L-histidine alkyl ester with an acid halide, chloroformate or pyrocarbonate in the presence of a base, hydrolysis of the alkyl-(S,Z)-2,4,5-triamidopent-4-enoate to obtain a (S)-alkyl 2,5-diamido-4-oxopentanoate, acid catalyzed hydrolysis of the (S)-alkyl 2,5-diamido-4-oxopentanoate followed by reaction with a metal thiocyanate to obtain the thiohistidine, protection of the sulfur of thiohistidine as the tert-butyl thioether, dialkylation of the primary amine to obtain a tertiary amine, quaternization of the tertiary amine, and removal of the protecting group to obtain the desired (S)-3-(2-mercapto-1H-imidazol-5-yl)-2-(trialkylammonio)propanoate (I). This process affords a better yield and is capable of practical application at large scale.

  这项发明涉及一种制备光学纯L-(+)-麦角硫胺的新工艺。L-麦角硫胺的化学合成过程包括以下步骤：将L-组氨酸烷基酯与酸卤、氯甲酸酯或吡碳酸酯在碱的存在下反应，水解烷基-(S,Z)-2,4,5-三氨基戊-4-烯酸酯以获得(S)-烷基2,5-二氨基-4-氧代戊酸酯，酸催化水解(S)-烷基2,5-二氨基-4-氧代戊酸酯，然后与金属硫氰酸盐反应以获得硫组氨酸，将硫组氨酸的硫保护为叔丁基硫醚，对一级胺进行二烷基化以获得三级胺，对三级胺进行季铵化，去除保护基以获得所需的(S)-3-(2-巯基-1H-咪唑-5-基)-2-(三烷基铵)丙酸酯(I)。这个工艺提供了更好的产率，并且适用于大规模实际应用。
• [EN] PROCESS FOR THE SYNTHESIS OF L-(+)-ERGOTHIONEINE<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE LA L-(+)-ERGOTHIONÉINE
  申请人：PHARMATECH INTERNATIONAL INC

  公开号：WO2009045413A1

  公开（公告）日：2009-04-09

  This invention relates to a novel process for the preparation of optically pure L- (+)-ergothioneine. The process for the chemical synthesis of L-ergothioneine comprises steps which consist of reacting L-histidine alkyl ester with an acid halide, chloroformate or pyrocarbonate in the presence of a base, hydrolysis of the alkyl-(S,Z)-2,4,5- triamidopent-4-enoate to obtain a (S)-alkyl 2,5-diamido-4-oxopentanoate, acid catalyzed hydrolysis of the (S)-alkyl 2,5-diamido-4-oxopentanoate followed by reaction with a metal thiocyanate to obtain the thiohistidine, protection of the sulfur of ttiiohistidine as the te/f-butyl thioether, dialkylation of the primary amine to obtain a tertiary amine.quaternization of the tertiary amine, and removal of the protecting group to obtain the desired (S)-3-(2-mercapto-1 H-imidazol-5-yl)-2-(trialkylammonio)propanoate (l). This process affords a better yield and is capable of practical application at large scale.

  本发明涉及一种制备光学纯L-(+)-麦角硫氨酸的新工艺。该化学合成L-麦角硫氨酸的过程包括以下步骤：在碱的存在下，将L-组氨酸烷基酯与酸卤、氯甲酸酯或者吡碳酸酯反应，水解烷基-(S,Z)-2,4,5-三酰基戊-4-烯酸酯以获得(S)-烷基2,5-二氨基-4-氧代戊酸酯，酸催化水解(S)-烷基2,5-二氨基-4-氧代戊酸酯，然后与金属硫氰酸盐反应以获得硫麦角氨酸，将硫麦角氨酸的硫保护为对叔丁基硫醚，将一级胺进行二烷基化以获得三级胺，对三级胺进行季铵化，去除保护基以获得所需的(S)-3-(2-巯基-1 H-咪唑-5-基)-2-(三烷基铵)丙酸盐(l)。该工艺具有更好的产量，并且可以在大规模实际应用中使用。
• Methods for Sterilizing Tissue
  申请人：Burgess Wilson

  公开号：US20110091353A1

  公开（公告）日：2011-04-21

  Methods are disclosed for sterilizing tissue to reduce the level of one or more active biological contaminants or pathogens therein, such as viruses, bacteria, (including inter- and intracellular bacteria, such as mycoplasmas, ureaplasmas, nanobacteria, chlamydia, rickettsias), yeasts, molds, fungi, prions or similar agents responsible, alone or in combination, for TSEs and/or single or multicellular parasites. The methods involve sterilizing one or more tissues with irradiation.

  本发明揭示了用于灭菌组织以减少其中一个或多个活性生物污染物或病原体水平的方法，例如病毒、细菌（包括细胞内和细胞外细菌，例如支原体、尿道支原体、纳米细菌、沙眼衣原体、立克次体）、酵母菌、霉菌、真菌、朊病毒或类似的单独或组合的代理人，对于TSEs和/或单个或多细胞寄生虫负责。该方法涉及使用辐照灭菌一个或多个组织。
• 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。