(S)-2-amino-N^α-(tert-butyloxycarbonyl)-6-(7',8'-dimethylisoalloxazin-10'-yl)hexanoic acid | 195812-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: (S)-2-amino-N^α-(tert-butyloxycarbonyl)-6-(7',8'-dimethylisoalloxazin-10'-yl)hexanoic acid
• 英文别名: (2S)-6-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 195812-22-7
• 化学式: C₂₃H₂₉N₅O₆
• 分子量: 471.513
• InChiKey: UHEHWAUERYDKJD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N^α-(tert-butyloxycarbonyl)-6-(7',8'-dimethylisoalloxazin-10'-yl)hexanoic acid 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以95%的产率得到(R)-2-amino-6-(7',8'-dimethylisoalloxazin-10'-yl)hexanoic acid
  参考文献：
  名称：

  Efficient Syntheses of a Flavin and an 8-Hydroxy-5-deazaflavin Amino Acid and Their Incorporation into Oligopeptides

  摘要：

  We report a convenient synthesis for the cofactor amino acids (S)-3 and (S)-4 in which the C-5-ribose chain of the original riboflavin and ribo-5-deazaflavin cofactors is replaced by a C-5-amino acid side chain. Both cofactor amino acids are available in enantiomerically pure form in gram quantities and can be incorporated into oligopeptides using a standard Fmoc-based solid-phase peptide synthesis protocol. The benzyl-protecting group of the 8-hydroxy-5-deazaflavin can be cleaved by hydrogenolysis directly on the peptide. This allows the investigation of the properties of the peptide bound redox active OH- and the deprotonated O--form of the deazaflavin. Due to the electron- and energy-transfer properties of both cofactors, applications of both amino acid in the preparation of peptide- and protein-based biosensors, of catalytically active peptides, or as chemical rulers for distance measurements in biopolymers based on the fluorescence resonance energy-transfer technology can be envisaged.

  DOI：

  10.1021/jo980643l
• 作为产物：
  描述：

  4，5-二甲-2-硝基苯胺 在 palladium on activated charcoal 过氧单硫酸 、 氢气 、 双氧水 、 硝酸 、 potassium acetate 、 硼酸 作用下， 以 乙醇 、 溶剂黄146 、 正丁醇 为溶剂， 反应 72.0h， 生成 (S)-2-amino-N^α-(tert-butyloxycarbonyl)-6-(7',8'-dimethylisoalloxazin-10'-yl)hexanoic acid
  参考文献：
  名称：

  Towards Artificial DNA-Repair Enzymes: Incorporation of a Flavin Amino Acid into DNA-Binding Oligopeptides

  摘要：

  DOI：

  10.1002/anie.199714611