Sodium;3-amino-6-azaniumylidene-9-[2-carboxy-4-[5-[3-[2-(methylaminooxymethyl)indol-1-yl]propylamino]pentylcarbamoyl]phenyl]xanthene-4,5-disulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Sodium;3-amino-6-azaniumylidene-9-[2-carboxy-4-[5-[3-[2-(methylaminooxymethyl)indol-1-yl]propylamino]pentylcarbamoyl]phenyl]xanthene-4,5-disulfonate
• 英文别名: sodium;3-amino-6-azaniumylidene-9-[2-carboxy-4-[5-[3-[2-(methylaminooxymethyl)indol-1-yl]propylamino]pentylcarbamoyl]phenyl]xanthene-4,5-disulfonate
• 化学式: C39H41N6NaO11S2
• 分子量: 856.9
• InChiKey: LUEGHZYOHWQJFD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.86
• 重原子数：
  59
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  297
• 氢给体数：
  6
• 氢受体数：
  14

文献信息

• PICTET-SPENGLER LIGATION FOR PROTEIN CHEMICAL MODIFICATION
  申请人：The Regents of the University of California

  公开号：EP2920148A1

  公开（公告）日：2015-09-23
• [EN] PICTET-SPENGLER LIGATION FOR PROTEIN CHEMICAL MODIFICATION<br/>[FR] LIGATURE PICTET-SPENGLER POUR LA MODIFICATION CHIMIQUE DE PROTÉINES
  申请人：UNIV CALIFORNIA

  公开号：WO2014078733A1

  公开（公告）日：2014-05-22

  Aldehyde- and ketone-functionalized proteins are promising new substrates for the development of chemically modified biotherapeutics and protein-based materials. Their reactive carbonyl groups are typically conjugated with a-effect nucleophiles, such as substituted hydrazines and alkoxyamines, to generate hydrazones and oximes, respectively. However, the resulting C=N linkages are susceptible to hydrolysis under physiologically relevant conditions, which limits their utility in biological systems. Here we introduce a Pictet-Spengler ligation that is based on the classic Pictet-Spengler reaction of aldehydes and tryptamine nucleophiles. The ligation exploits the bioorthogonal reaction of aldehydes and alkoxyamines to form an intermediate oxyiminium ion; this intermediate undergoes intramolecular C-C bond formation with an indole nucleophile to form an oxacarboline product that is hydrolytically stable. The reaction was utilized for site-specific chemical modification of glyoxal- and formylglycine-functionalized proteins, including an aldehyde-tagged variant of the therapeutic monoclonal antibody Herceptin. In conjunction with techniques for site-specific introduction of aldehydes into proteins, the Pictet-Spengler ligation offers a new means to generate stable bioconjugates for medical and materials applications.