N-Boc-Adt-Phe-OMe | 406199-57-3

• 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: N-Boc-Adt-Phe-OMe
• CAS: 406199-57-3
• 化学式: C₁₉H₂₆N₂O₅S₂
• 分子量: 426.558
• InChiKey: YLEJVBZUIWVSAV-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-Boc-Adt-Phe-OMe 在 甲酸 、 氯化亚砜 、 TEA 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 HCO-Met-Adt-Phe-OMe
  参考文献：
  名称：

  Exploring the interest of 1,2-Dithiolane ring system in peptide chemistry. Synthesis of a chemotactic tripeptide and x-ray crystal structure of a 4-amino-1,2-dithiolane-4-carboxylic acid derivative

  摘要：

  Due to their relevant biological functions and specific chemical reactivity 1,2-dithiolanes (five-membered cyclic disulfides) represent an emerging class of heterocyclic compounds. However, despite the extensive research centered on lipoic acid and its analogues, only very few data are at the present available on peptides containing this ring system. We report here synthesis, conformation and bioactivity of a fMLF-OMe analogue, namely For-Met-Adt-Phe-OMe (7), in which the residue of the 4-amino-1,2-dithiolane-4-carboxylic acid (Adt) (4) replaces the central L-leucine. The crystal conformation of the synthetic intermediate Boc-Adt-OMe (5) is also described and compared to that of lipoic acid (R-1,2-dithiolane-3-pentanoic acid) (3) and asparagusic acid (1,2-dithiolane-4-carboxylic acid) (2). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00256-5
• 作为产物：
  描述：

  N-tert-butyloxycarbonyl-2,2-bis(benzylthiomethyl)glycine methyl ester 在 sodium hydroxide 、 TEA 、 氨 、 sodium 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 生成 N-Boc-Adt-Phe-OMe
  参考文献：
  名称：

  Exploring the interest of 1,2-Dithiolane ring system in peptide chemistry. Synthesis of a chemotactic tripeptide and x-ray crystal structure of a 4-amino-1,2-dithiolane-4-carboxylic acid derivative

  摘要：

  Due to their relevant biological functions and specific chemical reactivity 1,2-dithiolanes (five-membered cyclic disulfides) represent an emerging class of heterocyclic compounds. However, despite the extensive research centered on lipoic acid and its analogues, only very few data are at the present available on peptides containing this ring system. We report here synthesis, conformation and bioactivity of a fMLF-OMe analogue, namely For-Met-Adt-Phe-OMe (7), in which the residue of the 4-amino-1,2-dithiolane-4-carboxylic acid (Adt) (4) replaces the central L-leucine. The crystal conformation of the synthetic intermediate Boc-Adt-OMe (5) is also described and compared to that of lipoic acid (R-1,2-dithiolane-3-pentanoic acid) (3) and asparagusic acid (1,2-dithiolane-4-carboxylic acid) (2). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00256-5

文献信息

• Synthetic and Electrochemical Studies of [2Fe2S] Complexes Containing a 4‐Amino‐1,2‐dithiolane‐4‐carboxylic Acid Moiety
  作者：Ulf‐Peter Apfel、Christian R. Kowol、Enrico Morera、Helmar Görls、Gino Lucente、Bernhard K. Keppler、Wolfgang Weigand

  DOI：10.1002/ejic.201000619

  日期：2010.11

  In the search for novel [FeFe] hydrogenase model systems several di- and tripeptides containing an 4-amino-1,2-dithiolane-4-carboxylic acid (Adt) moiety or N-phenylsulfonyl-Adt-OMe were treated with Fe 3 (CO)1 2. The resulting [FeFe] complexes were characterized by 1 H and 13 C NMR spectroscopy, mass spectrometry and elemental analysis. All complexes were investigated by cyclic voltammetry, and their

  在寻找新的 [FeFe] 氢化酶模型系统时，一些含有 4-氨基-1,2-二硫戊环-4-羧酸 (Adt) 部分或 N-苯磺酰基-Adt-OMe 的二肽和三肽用 Fe 3 ( CO)1 2. 所得的 [FeFe] 配合物通过 1 H 和 13 C NMR 光谱、质谱和元素分析进行​​表征。通过循环伏安法研究了所有配合物，并在不同溶剂中研究了它们催化质子还原为二氢的能力，作为酸浓度的函数。