D-phenylalanine p-nitrophenyl ester | 58848-63-8

• 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: D-phenylalanine p-nitrophenyl ester
• 英文别名: D-Phenylalanin-p-nitrophenylester；(4-nitrophenyl) (2R)-2-amino-3-phenylpropanoate
• CAS: 58848-63-8
• 化学式: C₁₅H₁₄N₂O₄
• 分子量: 286.287
• InChiKey: MHDRDPLGSXVGGV-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-phenylalanine p-nitrophenyl ester 在 Enterobacter cloacae P99 β-lactamase 作用下， 生成 对硝基苯酚 、 D-苯丙氨酸
  参考文献：
  名称：

  Serendipitous Discovery of α-Hydroxyalkyl Esters as β-Lactamase Substrates

  摘要：

  O-(1-Carboxy-1-alkyloxycarbonyl) hydroxamates were found to spontaneously decarboxylate in aqueous neutral buffer to form O-(2-hydroxyalkylcarbonyl) hydroxamates, While the former molecules do not react rapidly with serine beta-lactamases, the latter are quite good substrates of representative class A and C, but not D, enzymes, and particularly of a class C enzyme. The enzymes catalyze hydrolysis of these compounds to a mixture of the alpha-hydroxy acid and hydroxamate. Analogous compounds containing aryloxy leaving groups rather that hydroxamates are also substrates. Structure-activity experiments showed that the alpha-hydroxyl group was required for any substantial substrate activity. Although both D- and L-alpha-hydroxy acid derivatives were substrates, the former were preferred. The response of the class C activity to pH and to alternative nucleophiles (methanol and D-phenylalanine) suggested that the same active site functional groups participated in catalysis as for classical substrates. Molecular modeling was employed to explore how the alpha-hydroxy group might interact with the class C beta-lactamase active site. Incorporation of the alpha-hydroxyalkyl moiety into novel inhibitors will be of considerable interest.

  DOI：

  10.1021/bi101071r
• 作为产物：
  描述：

  (4-nitrophenyl) 3-phenyl-2-(tetradecanoylamino)propanoate 在 Tris buffer 、 potassium chloride 、 N-(N-dodecanoyl-L-histidyl)-L-leucine 、 (R)-(+)-N-α-methylbenzyl-NN-dimethyloctadecylammonium bromide 作用下， 以 水 、 乙腈 为溶剂， 生成 L-phenylalanine p-nitrophenyl ester 、 D-phenylalanine p-nitrophenyl ester
  参考文献：
  名称：

  N-（N-十二烷酰基-L-组氨酸基）-L-亮氨酸和阳离子手性表面活性剂对长链对硝基苯基N-酰基苯基丙氨酸的对映选择性脱酰基

  摘要：

  增强的对映选择性（ķ猫大号/ ķ猫d 5·5-5·7）的H [CH脱酰观察2 ] Ñ - 1 -CONHCH（CH 2 PH）CO 2 C ^ 6 ħ 4 NO 2 - p具有长酰基链（N 10-16）通过的comicelles ñ - （ñ -dodecanoyl-大号-组氨酰） -大号-亮氨酸和（- [R ）- （+） - ñ - α -methylbenzyl- NN -dimethyloctadecylammonium溴化物。

  DOI：

  10.1039/c39800000637

文献信息

• Salami; Jira; Otto, Hans-Hartwig, Pharmazie, 2005, vol. 60, # 3, p. 181 - 185
  作者：Salami、Jira、Otto, Hans-Hartwig

  DOI：——

  日期：——
• SASAKI, SHIGEKI;KOGA, KENJI, J. INCL. PHENOM., 7,(1989) N, C. 267-276
  作者：SASAKI, SHIGEKI、KOGA, KENJI

  DOI：——

  日期：——
• FORNASIER, ROBERTO;SCRIMIN, PAOLO;TONELLATO, UMBERTO;ZANTA, NICOLA, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 11, 88
  作者：FORNASIER, ROBERTO、SCRIMIN, PAOLO、TONELLATO, UMBERTO、ZANTA, NICOLA

  DOI：——

  日期：——
• Serendipitous Discovery of α-Hydroxyalkyl Esters as β-Lactamase Substrates
  作者：Ryan B. Pelto、R. F. Pratt

  DOI：10.1021/bi101071r

  日期：2010.12.14

  O-(1-Carboxy-1-alkyloxycarbonyl) hydroxamates were found to spontaneously decarboxylate in aqueous neutral buffer to form O-(2-hydroxyalkylcarbonyl) hydroxamates, While the former molecules do not react rapidly with serine beta-lactamases, the latter are quite good substrates of representative class A and C, but not D, enzymes, and particularly of a class C enzyme. The enzymes catalyze hydrolysis of these compounds to a mixture of the alpha-hydroxy acid and hydroxamate. Analogous compounds containing aryloxy leaving groups rather that hydroxamates are also substrates. Structure-activity experiments showed that the alpha-hydroxyl group was required for any substantial substrate activity. Although both D- and L-alpha-hydroxy acid derivatives were substrates, the former were preferred. The response of the class C activity to pH and to alternative nucleophiles (methanol and D-phenylalanine) suggested that the same active site functional groups participated in catalysis as for classical substrates. Molecular modeling was employed to explore how the alpha-hydroxy group might interact with the class C beta-lactamase active site. Incorporation of the alpha-hydroxyalkyl moiety into novel inhibitors will be of considerable interest.
• Enantioselective deacylation of long chain p-nitrophenyl N-acylphenyl-alanates by N-(N-dodecanoyl-L-histidyl)-L-leucine and a cationic chiral surfactant
  作者：Katsutoshi Ohkubo、Kiyoshi Sugahara、Kohji Yoshinaga、Ryuichi Ueoka

  DOI：10.1039/c39800000637

  日期：——

  Enhanced enantioselectivity (kcatL/kcatD 5·5–5·7) was observed in the deacylation of H[CH2]n– 1—CONHCH(CH2Ph)CO2C6H4NO2-p possessing long acyl chains (n 10–16) by comicelles of N-(N-dodecanoyl-L-histidyl)-L-leucine and (R)-(+)-N-α-methylbenzyl-NN-dimethyloctadecylammonium bromide.

  增强的对映选择性（ķ猫大号/ ķ猫d 5·5-5·7）的H [CH脱酰观察2 ] Ñ - 1 -CONHCH（CH 2 PH）CO 2 C ^ 6 ħ 4 NO 2 - p具有长酰基链（N 10-16）通过的comicelles ñ - （ñ -dodecanoyl-大号-组氨酰） -大号-亮氨酸和（- [R ）- （+） - ñ - α -methylbenzyl- NN -dimethyloctadecylammonium溴化物。