(1-Amino-propyl)-phosphonic acid diphenyl ester | 847780-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1-Amino-propyl)-phosphonic acid diphenyl ester
• 英文别名: 1-diphenoxyphosphorylpropan-1-amine
• CAS: 847780-93-2
• 化学式: C₁₅H₁₈NO₃P
• 分子量: 291.287
• InChiKey: YGXWWVSBOVFIGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1-Amino-propyl)-phosphonic acid diphenyl ester 在 三乙胺 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 2.0h， 生成 O,O-diphenyl [1-(2-selenomorpholin-4-yl-acetylamino)]propyl phosphonate
  参考文献：
  名称：

  SYNTHESIS OF O,O-DIPHENYL [SUBSTITUTED (2-SELENOMORPHOLIN-4-YL-ACETYL AMINO)] ALKYL PHOSPHONATES

  摘要：

  A series of O,O-diphenyl [substituted (2-selenomorpholin-4-yl-acetyl amino)] alkyl phosphonates were synthesized by the reactions of selenomorpholine with O,O-diphenyl 2-chloro- acetylamino alkyl phosphonates. The structures of all new compounds have been confirmed by H-1 NMR, P-31 NMR, IR spectroscopy, Mass spectroscopy and elemental analyses.

  DOI：

  10.1080/10426500490459687
• 作为产物：
  描述：

  亚磷酸三苯酯 在 氢溴酸 、 溶剂黄146 作用下， 反应 5.5h， 生成 (1-Amino-propyl)-phosphonic acid diphenyl ester
  参考文献：
  名称：

  Remote Binding Energy in Antibody Catalysis:  Studies of a Catalytically Unoptimized Specificity Pocket

  摘要：

  Binding interactions remote from the hydrolytic reaction center have been probed with substrate and phosphonate transition state analogues to understand how these types of interactions are used to promote catalysis in the 17E8 system, We find that the hapten-generated recogniton pocket in 17E8 has properties that are analogous to those of specificity pockets in enzymes, pie have also found that there are specific requirements to form catalytically productive interactions between the side chain and the recognition pocket including conformation, size, and geometry. An additional requirement includes Favorable simultaneous interactions between the side chain and binding packet along with favorable interactions with the oxyanion hole. The 17E8 side chain recognition pocket seems to be less catalytically efficient than analogous pockets in enzymatic systems. The apparent binding energy gained from the methylene-packet interactions in the 17E8 system is significantly smaller than those observed in natural enzymes. Furthermore, 17E8 does not use specific interactions in the recognition pocket to significantly affect catalytic turnover (k(cat)) which is thought to be a trait of an unoptimized catalyst. Analysis of the crystal structure of the 17E8,hapten complex has allowed for the identification of differences between the active sites of 17E8; and several proteases, The identified differences give insight to the sources of the inefficient use of binding energy.

  DOI：

  10.1021/ja983017e

文献信息

• N-(Phosphonoacetyl)amino phosphonates. Phosphonate analogs of N-(phosphonoacetyl)-L-aspartic acid (PALA)
  作者：Pawel Kafarski、Barbara Lejczak、Przemyslaw Mastalerz、Danuta Dus、Czeslaw Radzikowski

  DOI：10.1021/jm00149a002

  日期：1985.11

  Michaelis-Arbuzov reaction of N-(chloroacetyl)amino phosphonic acids or their esters, followed by acidolysis, gives moderate yields of N-(phosphonoacetyl) derivatives of a variety of (aminoalkyl)phosphonic acids, including analogues of the cytostatic agent PALA, in which the alpha- or beta-carboxylic groups in the aspartate moiety are replaced by a PO3H2 function. Assay of cytostatic activity with

  N-（氯乙酰基）氨基膦酸或其酯的Michaelis-Arbuzov反应，然后酸解，可得到中等收率的各种（氨基烷基）膦酸的N-（膦酰基乙酰基）衍生物，包括细胞抑制剂PALA的类似物。天冬氨酸部分中的α-或β-羧基被PO3H2取代。用人KB细胞系的细胞抑制活性的测定表明，用PO 3 H 2取代PALA中的任何COOH基团会导致细胞抑制活性的完全丧失。在该报告中描述的其他[N-（膦酰基乙酰基）氨基]烷基膦酸的情况下也未观察到活性。
• Multiplexed Probing of Proteolytic Enzymes Using Mass Cytometry-Compatible Activity-Based Probes
  作者：Marcin Poreba、Katarzyna M. Groborz、Wioletta Rut、Milind Pore、Scott J. Snipas、Matej Vizovisek、Boris Turk、Peter Kuhn、Marcin Drag、Guy S. Salvesen

  DOI：10.1021/jacs.0c06762

  日期：2020.9.30

  activity-based probes, small inhibitors equipped with a detectable tag, commonly a fluorophore. Due to the spectral overlap of these commonly used fluorophores, multiplex analysis becomes limited. To overcome this, we developed a series of protease-selective lanthanide-labeled probes compatible with mass cytometry giving us the ability to monitor the activity of multiple proteases in parallel. Using these

  含有催化活性形式的酶的蛋白质组子集可以通过使用针对单个特定酶的探针进行询问。此类酶的一个子集是经常使用基于活性的探针、配备有可检测标签（通常是荧光团）的小型抑制剂进行研究的蛋白酶。由于这些常用荧光团的光谱重叠，多重分析变得有限。为了克服这个问题，我们开发了一系列与质谱流式细胞仪兼容的蛋白酶选择性镧系元素标记探针，使我们能够并行监测多种蛋白酶的活性。使用这些探针，我们能够识别具有不同活性位点几何形状的四种蛋白酶在三种细胞系和外周血单核细胞中的分布。这为使用质谱流式细胞仪进行多重酶活性检测提供了框架。