3-nitrophenyl phosphate | 13388-91-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 3-nitrophenyl phosphate
• 英文别名: phosphoric acid mono-(3-nitro-phenyl ester)；Phosphorsaeure-mono-(3-nitro-phenylester)；3-nitrophenylphosphate；Phosphorsaeure-<3-nitro-phenylester>；<3-Nitro-phenyl>-dihydrogenphosphat；Mono-(m-nitrophenyl)-phosphat；3-Nitrophenyl dihydrogen phosphate；(3-nitrophenyl) dihydrogen phosphate
• CAS: 13388-91-5
• 化学式: C₆H₆NO₆P
• 分子量: 219.09
• InChiKey: XBUUVLVJXNRBPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-nitrophenyl phosphate 在 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 uridine-5'-(3-nitrophenyl)-tetraphosphate triethylammonium
  参考文献：
  名称：

  Pyrimidine Nucleotides with 4-Alkyloxyimino and Terminal Tetraphosphate δ-Ester Modifications as Selective Agonists of the P2Y₄ Receptor

  摘要：

  P2Y(2) and P2Y(4) receptors are G protein-coupled receptors, activated by UTP and dinudeoside tetraphosphates, which are difficult to distinguish pharmacologically for lack of potent and selective ligands. We structurally varied phosphate and uracil moieties in analogues of pyrimidine nucleoside 5'-triphosphates and 5'-tetraphosphate esters. P2Y(4) receptor potency in phospholipase C stimulation in transfected 1321N1 human astrocytoma cells was enhanced in N-4-alkyloxycytidine derivatives. OH groups on a terminal delta-glucose phosphoester of uridine 5'-tetraphosphate were inverted or substituted with H or F to probe H-bonding effects. N-4-(Phenylpropoxy)-CTP 16 (MRS4062), Up(4)-[1]3'-deoxy-3'-fluoroglucose 34 (MRS2927), and N-4-(phenylethoxy)-CTP 15 exhibit >= 10-fold selectivity for human P2Y(4) over P2Y(2) and P2Y(6) receptors (EC50 values 23, 62, and 73 nM, respectively). delta-3-Chlorophenyl phosphoester 21 of Up(4) activated P2Y(2) but not P2Y(4) receptor. Selected nucleotides tested for chemical and enzymatic stability were much more stable than UTP. Agonist docking at CXCR4-based P2Y(2) and P2Y(4) receptor models indicated greater steric tolerance of N-4-phenylpropoxy group at P2Y(4). Thus, distal structural changes modulate potency, selectivity, and stability of extended uridine tetraphosphate derivatives, and we report the first P2Y(4) receptor-selective agonists.

  DOI：

  10.1021/jm101591j
• 作为产物：
  描述：

  间硝基苯酚 生成 3-nitrophenyl phosphate
  参考文献：
  名称：

  底物磷酸化碱性磷酸酶中S N 2（P）机制的证据

  摘要：

  已经测量了一系列作为碱性磷酸酶底物的烷基磷酸，芳基磷酸和芳基酰胺磷酸的Michaelis-Menten参数。在pH范围内测量对-溴苯基酰胺基磷酸酯的动力学参数，结果包括无机磷酸盐的抑制表明酰胺是酶的正常底物。对于所有基材，参数k 0几乎没有变化；参数k 0 / K m是衡量游离酶被游离底物磷酸化的速率常数的度量，在烷基磷酸酯系列中显示出对空间因子的高选择性。酰胺基磷酸盐的含量是其的十倍以上少比在所述芳基磷酸酯反应ķ 0 / ķ米参数和分别计算为60000倍的过小小号Ñ 1（P）的机制。这两个结果以及从文献中得出的论点都表明，S N 2（P）的磷酸化机制涉及对磷的直接亲核攻击。取代的芳基氨基磷酸酯与吸电子取代基的反应性降低，表明酸催化。建议磷酸酶作用所必需的锌（II）促进S N通过与底物络合并中和氧上的负电荷，从而激活了磷的亲核攻击，从而形成了磷的2（P）机理。

  DOI：

  10.1039/j29710001973

文献信息

• Transition States and Control of Substrate Preference in the Promiscuous Phosphatase PP1
  作者：Yuan Chu、Nicholas H. Williams、Alvan C. Hengge

  DOI：10.1021/acs.biochem.7b00441

  日期：2017.8.1

  monoester substrate, PP1γ catalyzes the hydrolysis of aryl methylphosphonates, fluorophosphate esters, phosphorothioate esters, and phosphodiesters, with second-order rate accelerations that fall within the narrow range of 1011–1013. In contrast to the different transition states in the uncatalyzed hydrolysis reactions of these substrates, PP1γ catalyzes their hydrolysis through similar transition states

  催化混杂酶是生物化学的一个有吸引力的前沿领域，因为酶混杂不仅可以通过基因复制机制合理地解释酶的进化，而且可以通过模仿这种进化过程来提供改变蛋白质催化功能的有效途径。PP1γ是一种有效的混杂磷酸酶，可水解基于单阴离子和双阴离子磷酸酯的底物。除了其天然的磷酸单酯底物外，PP1γ还催化芳基甲基膦酸酯，氟代磷酸酯，硫代磷酸酯和磷酸二酯的水解，其二级速率加速范围在10 11 –10 13的狭窄范围内。。与这些底物的未催化水解反应中的不同过渡态相反，PP1γ通过相似的过渡态催化其水解。PP1γ不会催化硫酸酯的水解，这是出乎意料的。PP1γ活性位点可耐受结合的配体的几何形状变化，即使在初始酶-底物复合物和过渡态中，其空间要求可能会干扰转移基团定位的底物也可有效催化状态。精氨酸221向赖氨酸的保守突变导致突变体，其是对单阴离子底物更有效的催化剂。
• A Structural and Functional Model of Dinuclear Metallophosphatases
  作者：Nicholas H. Williams、Anne-Marie Lebuis、Jik Chin

  DOI：10.1021/ja9827797

  日期：1999.4.1

  Hydrolysis of four substituted phenyl phosphate monoesters, each coordinated to a dinuclear Co(III) complex, was studied ([Co2(tacn)2(OH)2O3P(OAr)}]2+; tacn = 1,4,7-triazacyclononane; substituent ...

  研究了四种取代的苯基磷酸单酯的水解，每种都配位到双核 Co(III) 复合物上 ([Co2(tacn)2(OH)2O3P(OAr)}]2+；tacn = 1,4,7-三氮杂环壬烷；取代基...
• Inhibiting undesirable taste in oral compositions
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0845217A1

  公开（公告）日：1998-06-03

  The present invention relates to a method for inhibiting an undesirable taste in oral compositions such as foods, beverages, dental compositions, and pharmaceuticals. The present invention also relates to oral and pharmaceutical compositions comprising undesirable tasting compounds wherein undesirable tastes are inhibited by the addition of an inhibitor of intracellular phosphatase enzymes of taste cells to said oral and pharmaceutical compositions. Said inhibitor is selected from phosphates, thiophosphates, phosphonates, vanadates, bisphosphates, bisphosphonates, phosphate-phosphonates, thiophosphate-phosphates, thiophosphate-phosphonates, their physiologically-relevant salts and esters, and mixtures thereof.

  本发明涉及一种抑制口服组合物（如食品、饮料、牙科组合物和药物）中不良味道的方法。本发明还涉及包含不良味道化合物的口服和药物组合物，其中通过在所述口服和药物组合物中添加味觉细胞内磷酸酶抑制剂来抑制不良味道。所述抑制剂选自磷酸盐、硫代磷酸盐、膦酸盐、钒酸盐、双磷酸盐、双膦酸盐、磷酸盐-膦酸盐、硫代磷酸盐-磷酸盐、硫代磷酸盐-膦酸盐、它们的生理相关盐和酯，以及它们的混合物。
• Method for producing meta type polyaniline
  申请人：Honda Giken Kogyo Kabushiki Kaisha

  公开号：EP1090944A2

  公开（公告）日：2001-04-11

  A novel method for producing a meta type polyaniline, comprising polymerizing aniline in at least one organic solvent selected from N-methyl-2-pyrrolidone, N,N-dimethyl sulfoxide, N,N-dimethylacetamide and N,N-dimethylformamide, in the presence of at least one oxidizing agent selected from ammonium peroxodisulfate, iron(III) chloride, manganese dioxide and hydrogen peroxide, at -20°C to 50°C.

  一种生产元型聚苯胺的新方法，包括在至少一种选自 N-甲基-2-吡咯烷酮、N,N-二甲基亚砜、N,N-二甲基乙酰胺和 N,N-二甲基甲酰胺的有机溶剂中，在至少一种选自过氧化二硫酸铵、氯化铁（III）、二氧化锰和过氧化氢的氧化剂存在下，于 -20°C 至 50°C 的温度下聚合苯胺。
• Proton conducting polymer, method for producing the same, solid polymer electrolyte and electrode
  申请人：Honda Giken Kogyo Kabushiki Kaisha

  公开号：EP1085034A1

  公开（公告）日：2001-03-21

  A proton conducting polymer obtained by blending an organic phosphoric acid compound solution with a meta type polyaniline solution; a solid polymer electrolyte for a fuel cell comprising the proton conducting polymer, which is excellent in proton conductivity, methanol barrier property and dopant stability in an aqueous solution of methanol; and an electrode comprising the proton conducting and fine catalyst particles carried on porous particles.

  一种质子传导聚合物，由有机磷酸化合物溶液与元型聚苯胺溶液混合而成；一种燃料电池用固体聚合物电解质，由质子传导聚合物组成，该聚合物在甲醇水溶液中具有优异的质子传导性、甲醇阻隔性和掺杂稳定性；以及一种电极，由质子传导聚合物和多孔颗粒上的细小催化剂颗粒组成。