(2S)-2-acetamido-3-[3-(3,5-dioxo-4-phenyl-1,2,4-triazolidin-1-yl)-4-hydroxyphenyl]-N-methylpropanamide | 1207170-29-3

• 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: (2S)-2-acetamido-3-[3-(3,5-dioxo-4-phenyl-1,2,4-triazolidin-1-yl)-4-hydroxyphenyl]-N-methylpropanamide
• CAS: 1207170-29-3
• 化学式: C₂₀H₂₁N₅O₅
• 分子量: 411.417
• InChiKey: HJNZEHXDISUOFK-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-苯基-1,2,4-三唑啉-3,5-二酮 、 (alphaS)-alpha-(乙酰氨基)-4-羟基-N-甲基-苯丙酰胺 以 乙腈 为溶剂， 以65%的产率得到(2S)-2-acetamido-3-[3-(3,5-dioxo-4-phenyl-1,2,4-triazolidin-1-yl)-4-hydroxyphenyl]-N-methylpropanamide
  参考文献：
  名称：

  Tyrosine Bioconjugation through Aqueous Ene-Type Reactions: A Click-Like Reaction for Tyrosine

  摘要：

  A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in a buffered aqueous Solution. This reaction provides a novel synthetic approach to bispecific antibodies. We believe this reaction will find broad utility in peptide and protein chemistry and in the chemistry of phenol-containing compounds.

  DOI：

  10.1021/ja909062q

文献信息

• Tyrosine Bioconjugation through Aqueous Ene-Like Reactions
  申请人：Barbas, III Carlos F.

  公开号：US20120289682A1

  公开（公告）日：2012-11-15

  A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an Ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in buffered aqueous solution. This reaction provides a novel synthetic approach to bispecific antibodies. This reaction will find broad utility in peptide and protein chemistry and in the chemistry of phenol-containing compounds.

  报道了一种新型多功能环状二氮基二羧酰胺类化合物，通过Ene反应与苯酚和酪氨酸的苯基侧链高效选择性反应。这种温和的水相酪氨酸连接反应适用于广泛的pH范围，并扩展了小分子、肽和蛋白质修饰的水相化学反应库。该酪氨酸连接反应可与缓冲水溶液中的天然酶和抗体标记兼容。该反应提供了一种新的双特异性抗体合成方法。该反应将在肽和蛋白质化学以及含酚化合物的化学中发挥广泛的实用价值。
• US8765920B2
  申请人：——

  公开号：US8765920B2

  公开（公告）日：2014-07-01
• [EN] TYROSINE BIOCONJUGATION THROUGH AQUEOUS ENE-LIKE REACTIONS<br/>[FR] BIOCONJUGAISON DE LA TYROSINE PAR DES RÉACTIONS DE TYPE ÈNE EN MILIEU AQUEUX
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2011079315A1

  公开（公告）日：2011-06-30

  A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an Ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in buffered aqueous solution. This reaction provides a novel synthetic approach to bispecific antibodies. This reaction will find broad utility in peptide and protein chemistry and in the chemistry of phenol-containing compounds.