1-methyl-5-thiol-L-histidine | 62982-24-5

• 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: 1-methyl-5-thiol-L-histidine
• 英文别名: L-5-sulfanyl-1-methylhistidine；1-Methyl-5-sulfanyl-L-histidine；(2S)-2-amino-3-(1-methyl-5-sulfanylimidazol-4-yl)propanoic acid
• CAS: 62982-24-5
• 化学式: C₇H₁₁N₃O₂S
• 分子量: 201.249
• InChiKey: WBKFBEXRADDJIW-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  82.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methyl-5-thiol-L-histidine 在 air 、 氢碘酸 作用下， 以 水 为溶剂， 反应 24.0h， 生成 (S)-2-Amino-3-{5-[5-((S)-2-amino-2-carboxy-ethyl)-3-methyl-3H-imidazol-4-yldisulfanyl]-1-methyl-1H-imidazol-4-yl}-propionic acid
  参考文献：
  名称：

  Isolation and structure of a new sulphur-containing aminoacid from sea urchin eggs

  摘要：

  DOI：

  10.1016/s0040-4039(00)88597-4
• 作为产物：
  描述：

  (S)-2-Amino-3-{5-[5-((S)-2-amino-2-carboxy-ethyl)-3-methyl-3H-imidazol-4-yldisulfanyl]-1-methyl-1H-imidazol-4-yl}-propionic acid 在 1,4-二巯基-2,3-丁二醇 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以69%的产率得到1-methyl-5-thiol-L-histidine
  参考文献：
  名称：

  NOVEL 5-ACYLSULFANYL-HISTIDINE COMPOUNDS AS PRECURSORS OF THE CORRESPONDING 5-SULFANYLHISTIDINES AND THEIR DISULFIDES

  摘要：

  本发明涉及一种5-酰基硫酰基组氨酸类化合物及其衍生物，通式（I）如下：其中R1至R3为H、烷基，特别是CH3；R4为H、烷基，特别是CH3，烷基（C═O）取代基烷基（C═O）、芳基（C═O）；β-丙氨酸基（H2NCH2CH2（C═O））；α-氨基酰基；R5为烷基，特别是甲基、苯基。本发明还涉及使用该化合物制备5-硫酰基组氨酸类化合物及其衍生物，以及相应的二硫化物；以及其制备的各种方法。

  公开号：

  US20170190691A1

文献信息

• NOVEL 5-ACYLSULFANYL-HISTIDINE COMPOUNDS AS PRECURSORS OF THE CORRESPONDING 5-SULFANYLHISTIDINES AND THEIR DISULFIDES
  申请人：TETRAGEDRON

  公开号：US20170190691A1

  公开（公告）日：2017-07-06

  The invention relates to a compound of the 5-acylsulfanyl-histidine type and the derivatives thereof, of general formula (I), wherein R1 to R3=H, alkyl, especially CH3; R4=H, alkyl, especially CH3, alkyle(C═O), substituted alkyl (C═O), aryl (C═O); β-alanyl (H2NCH2CH2 (C═O); α-amino-acyl; R5=alkyl, especially methyl, phenyl. The invention also relates to the use of said compound for producing compounds of the 5-sulfanyl-histidine type and the derivatives thereof, in addition to corresponding disulfides; and to the various methods for the production thereof.

  本发明涉及一种5-酰基硫酰基组氨酸类化合物及其衍生物，通式（I）如下：其中R1至R3为H、烷基，特别是CH3；R4为H、烷基，特别是CH3，烷基（C═O）取代基烷基（C═O）、芳基（C═O）；β-丙氨酸基（H2NCH2CH2（C═O））；α-氨基酰基；R5为烷基，特别是甲基、苯基。本发明还涉及使用该化合物制备5-硫酰基组氨酸类化合物及其衍生物，以及相应的二硫化物；以及其制备的各种方法。
• NOUVEAUX COMPOSES DE TYPE 5-ACYLSULFANYL-HISTIDINE EN TANT QUE PRECURSEURS DES 5-SULFANYLHISTIDINES CORRESPONDANTES ET DE LEURS DISULFURES
  申请人：Tetrahedron

  公开号：EP3148973A1

  公开（公告）日：2017-04-05
• Ergothioneine Production Through Metabolic Engineering
  申请人：LIU Pinghua

  公开号：US20150225755A1

  公开（公告）日：2015-08-13

  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.
• 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).
• 5-SULFANYLHISTIDINES AND THEIR DISULFIDES AND METHOD OF PREPARATION THEREOF
  申请人：TETRAHEDRON

  公开号：US20180258077A1

  公开（公告）日：2018-09-13

  The invention relates to a compound of the 5-acylsulfanyl-histidine type and the derivatives thereof, of general formula (I), wherein R1 to R3=H, alkyl, especially CH3; R4=H, alkyl, especially CH3, alkyle(C=0), substituted alkyl (C═O), aryl (C═O); β-alanyl (H2NCH2CH2 (C═O); α-amino-acyl; R5=alkyl, especially methyl, phenyl. The invention also relates to the use of said compound for producing compounds of the 5-sulfanyl-histidine type and the derivatives thereof, in addition to corresponding disulfides; and to the various methods for the production thereof.