(2S)-3-[2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1H-imidazol-5-yl]-2-(trimethylazaniumyl)propanoate | 1587622-54-5

• 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: (2S)-3-[2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1H-imidazol-5-yl]-2-(trimethylazaniumyl)propanoate
• CAS: 1587622-54-5
• 化学式: C₁₂H₂₀N₄O₄S
• 分子量: 316.381
• InChiKey: XZNPNXSZABHULP-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-半胱氨酸 、 hercynine 在 溴 作用下， 生成 (2S)-3-[2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1H-imidazol-5-yl]-2-(trimethylazaniumyl)propanoate
  参考文献：
  名称：

  Cysteine Oxidation Reactions Catalyzed by a Mononuclear Non-heme Iron Enzyme (OvoA) in Ovothiol Biosynthesis

  摘要：

  OvoA in ovothiol biosynthesis is a mononuclear non-heme iron enzyme catalyzing the oxidative coupling between histidine and cysteine. It can also catalyze the oxidative coupling between hercynine and cysteine, yet with a different regio-selectivity. Due to the potential application of this reaction for industrial ergothioneine production, in this study, we systematically characterized OvoA by a combination of three different assays. Our studies revealed that OvoA can also catalyze the oxidation of cysteine to either cysteine sulfinic acid or cystine. Remarkably, these OvoA-catalyzed reactions can be systematically modulated by a slight modification of one of its substrates, histidine.

  DOI：

  10.1021/ol5005438

文献信息

• PROCESS FOR SYNTHESIZING ERGOTHIONEINE AND RELATED COMPOUNDS
  申请人：University of Cape Town

  公开号：US20170305865A1

  公开（公告）日：2017-10-26

  The invention provides a process for synthesising a compound of formula V wherein: n is 0, 1 or 2; and R is H or or a physiologically acceptable salt, tautomer, stereoisomer or mixture of stereoisomers thereof. The process utilizes a N-benzyl protected histidine rather than the unprotected form of histidine. The process of the invention comprises the steps of: (a) deprotecting a N-benzyl protected histidine of formula 11 to form N-benzyl histidine of formula 12; (b) converting compound 12 to (S)-3-(1-benzyl-1H-imidazol-4-yl)-2-(dimethylamino)propanoic acid of formula 13; (c) converting compound 13 to (2S)-N,N,N-2-trimethylethanaminium-3-(1-benzyl-1H-imidazol-4-yl)propanoic acid of formula 14; (d) brominating the imidazole ring of the compound of formula 14 to form 5-bromohercynine lactone (reactive intermediate); and (e) converting the 5-bromohercynine lactone of step (d) to (6-amino-6-carboxyethyl)ergothioneine sulfide of formula 15. The process optionally further includes one of steps (f) to (h): (f) converting the compound of formula 15 to a sulfoxide; (g) converting the compound of formula 15 to a sulfone; or (h) converting the compound of formula 15 to ergothioneine (ESH).
• US9908854B2
  申请人：——

  公开号：US9908854B2

  公开（公告）日：2018-03-06
• Cysteine Oxidation Reactions Catalyzed by a Mononuclear Non-heme Iron Enzyme (OvoA) in Ovothiol Biosynthesis
  作者：Heng Song、Ampon Sae Her、Fiona Raso、Zhibin Zhen、Yuda Huo、Pinghua Liu

  DOI：10.1021/ol5005438

  日期：2014.4.18

  OvoA in ovothiol biosynthesis is a mononuclear non-heme iron enzyme catalyzing the oxidative coupling between histidine and cysteine. It can also catalyze the oxidative coupling between hercynine and cysteine, yet with a different regio-selectivity. Due to the potential application of this reaction for industrial ergothioneine production, in this study, we systematically characterized OvoA by a combination of three different assays. Our studies revealed that OvoA can also catalyze the oxidation of cysteine to either cysteine sulfinic acid or cystine. Remarkably, these OvoA-catalyzed reactions can be systematically modulated by a slight modification of one of its substrates, histidine.