PapAlaGluTrpAlaSerLysVal; Pap = p-azidophenylalanine | 1337529-91-5

• 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: PapAlaGluTrpAlaSerLysVal; Pap = p-azidophenylalanine
• CAS: 1337529-91-5
• 化学式: C₄₅H₆₃N₁₃O₁₂
• 分子量: 978.075
• InChiKey: LOHKYCODTBJSPZ-USXSCMIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  70.0
• 可旋转键数：
  29.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  415.12
• 氢给体数：
  13.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  dimethyl-4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenylphosphonite 、 PapAlaGluTrpAlaSerLysVal; Pap = p-azidophenylalanine 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Staudinger-Phosphonite Reactions for the Chemoselective Transformation of Azido-Containing Peptides and Proteins

  摘要：

  Site-specific functionalization of proteins by bloorthogonal modification offers a convenient pathway to create, modify, and study biologically active biopolymers. In this paper the Staudinger reaction of aryl-phosphonites for the chemoselective functionalization of azido-peptides and proteins was probed. Different water-soluble phosphonites with ollgoethylene substituents were synthesized and reacted with unprotected azido-containing peptides in aqueous systems at room temperature in high conversions. Finally, the Staudinger-phosphonite reaction was successfully applied to the site-specific modification of the protein calmodulin.

  DOI：

  10.1021/ol2020175

文献信息

• Chemoselective Bioconjugation of Triazole Phosphonites in Aqueous Media
  作者：M. Robert J. Vallée、Paul Majkut、Dagmar Krause、Michael Gerrits、Christian P. R. Hackenberger

  DOI：10.1002/chem.201404690

  日期：2015.1.12

  versatile phosphonite building blocks with improved stability against hydrolysis were used for the efficient metal‐free functionalization of peptides and proteins in aqueous buffers at low micromolar concentrations. The application of this protocol to the immobilization of a Rasa1‐SH2 domain revealed high binding affinity to the human T‐cell protein ADAP and supports the applicability of triazole phosphonites

  具有低水解稳定性的易于使用且用途广泛的亚膦酸酯构建基块可用于在低微摩尔浓度的水性缓冲液中对肽和蛋白质进行有效的无金属官能化。该协议在固定Rasa1-SH2结构域中的应用显示出对人T细胞蛋白质ADAP的高结合亲和力，并支持三唑亚膦酸酯用于蛋白质修饰而不损害其功能。