glycine p-nitrophenyl ester hydrobromide | 7413-60-7

• 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: glycine p-nitrophenyl ester hydrobromide
• 英文别名: 4-nitrophenyl glycinate hydrobromide；HBr*H-Gly-ONp；glycine-(4-nitro-phenyl ester); hydrobromide；Glycin-(4-nitro-phenylester); Hydrobromid；(4-nitrophenyl) 2-aminoacetate;hydrobromide
• CAS: 7413-60-7
• 化学式: BrH*C₈H₈N₂O₄
• 分子量: 277.074
• InChiKey: JERUTMRCCUPUKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  98.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  glycine p-nitrophenyl ester hydrobromide 在 palladium on activated charcoal 盐酸 作用下， 以 甲醇 为溶剂， 生成 ((S)-2-Amino-3-phenyl-propionylamino)-acetic acid 4-nitro-phenyl ester
  参考文献：
  名称：

  Selective reduction of the carbobenzoxy group in carbobenzoxyamino acid and peptide p-nitrophenyl esters

  摘要：

  DOI：

  10.1021/jo01270a055
• 作为产物：
  描述：

  对硝基苯酚 在 氢溴酸 、 溶剂黄146 作用下， 生成 glycine p-nitrophenyl ester hydrobromide
  参考文献：
  名称：

  Wieland; Heinke, Justus Liebigs Annalen der Chemie, 1958, vol. 615, p. 184,195

  摘要：

  DOI：

文献信息

• <b>On Cysteine and Cystein Peptides. II. S-Acylcysteines in Peptide Synthesis</b>
  作者：Leonidas. Zervas、Iphigenia. Photaki、Nicolaos. Ghelis

  DOI：10.1021/ja00892a027

  日期：1963.5

  molecular models reveals very low, if any, strain in the planar arrangements shown for the three donor groups of the ligan’d. Since resonance between the imine and aromatic ring would tend to keep the bonds adjacent to the imine nitrogens in the same plane, the planar arrangement for the ligands shown in B and C is favored over other possible structures. Additional evidence for the proposed chelate

  分子模型显示，配体的三个供体组显示的平面排列中的应变非常低（如果有的话）。由于亚胺和芳环之间的共振倾向于将与亚胺氮相邻的键保持在同一平面上，因此 B 和 C 中所示配体的平面排列优于其他可能的结构。可以通过比较图 1 中的红外光谱获得所提出的螯合物结构的其他证据。在 2500-2600 cm 附近是否存在宽带。-l 表示 Cu(I1) 螯合物没有分子间氢键，而 Fe(II1) 和 Ni(I1) 螯合物的这种键合量增加。这些带的强度与无、一、和两个能够形成分子间氢键的吡啶鎓质子，分别如结构 A、B 和 C 所示。根据红外证据，对于 Fe(II1) 和 Ni(I1)，不能排除水与金属配位且 3-吡啶醇基团参与分子间氢键的替代结构。另一方面，根据已知的金属离子与有机配体中各种类型的供体基团之间的亲和力，这种替代结构被认为是不可能的。
• Amino acids and peptides. IX Synthesis and physicochemical properties of cyclic peptides.
  作者：KAZUTAKA TANIZAWA、KUNIO OKUMURA、HIROMI ITOH、YASUMARU HATANAKA、YUICHI KANAOKA

  DOI：10.1248/cpb.34.4001

  日期：——

  A series of cyclic peptides varying in ring size and in amino acid constituents was synthesized. Cyclization reactions of linear peptides were carried out by the azide, p-nitrophenyl ester, N-hydroxysuccinimide ester and diethyl phosphorocyanidate methods. Intermolecular cyclodimerization was also applied for the preparation of a cyclic hexapeptide. The reaction yield in each cyclization method was found to be sufficient for preparative purposes. Conformational analysis of the cyclic peptides was carried out by using proton nuclear magnetic resonance. The temperature dependency of peptide NH signals revealed that hexapeptides with the cyclo(-Gly-Xxx-Gly-)2 sequence are stabilized by intramolecular hydrogen bonding and are resistant to temperatureinduced conformational change.

  合成了一系列环状肽，具有不同的环大小和氨基酸成分。通过叠氮化物、对硝基苯基酯、N-羟基琥珀酰亚胺酯和二乙基磷氰酸盐法对线性肽进行环化反应。还应用了分子间环二聚化法制备环状六肽。每种环化方法的反应产率均被发现足够用于制备目的。使用质子核磁共振对环状肽进行了构象分析。肽NH信号的温度依赖性表明，具有环状(-Gly-Xxx-Gly-)2序列的六肽通过分子内氢键得到稳定，并且对温度诱导的构象变化具有抗性。
• Novel bicyclic chiral crown ethers having a p-xylenedioxy unit with improved complex stability and rate-enhancement in the intra-complex thiolysis of .ALPHA.-amino acid ester salts.
  作者：Tatsuro YASUKATA、Shigeki SASAKI、Kenji KOGA

  DOI：10.1248/cpb.39.530

  日期：——

  Novel bicyclic chiral crown ethers having an α, α'-p-xylenedioxy unit were synthesized. Crown dithiol 1 with a p-xylenedioxy bridge-structure perfomed intra-complex thiolysis with α-amino acid p-nitrophenyl ester HBr salts much faster than the corresponding dithiol 3 without the bridge-structure. A 1H-NMR study suggested that the increased rate of intracomplex thiolysis is due to increased stability of the intermediary complex during the reaction.

  合成了具有 α, α'-p-xylenedioxy 单元的新型双环手性冠醚。具有对二亚甲氧基桥结构的冠醚 1 与α-氨基酸对硝基苯酯 HBr 盐进行络合物内硫解的速度比相应的无桥结构的二硫醇 3 快得多。1H-NMR 研究表明，络合物内硫解速度的提高是由于中间络合物在反应过程中稳定性的提高。
• The uncatalysed and copper(II) promoted hydrolysis of 4-nitrophenyl glycinate
  作者：Robert W. Hay、Arup K. Basak

  DOI：10.1039/dt9860000039

  日期：——

  mol–1 s–1 at 35 °C. The hydrolysis of the ester is strongly promoted by copper(II), and under the experimental conditions employed, it has been shown that the metal-ion promotion involves the steps (ii) and (iii) with KM= 2.7 × 102 dm3 mol–1 and kOH= 6.6 × 106 Cu2++ L[graphic omitted][CuL]2+(ii), [CuL]2–+ OH– [graphic omitted] Products (iii) dm3 mol–1 s–1 at 35 °C. Base hydrolysis of [CuL]2+ is ca. 3 ×

  在I = 0.1 mol dm –3（KNO 3）和35°C的pH范围内，对4-硝基苯基甘氨酸的无催化水解进行了研究。4-硝基苯基甘氨酸的电离平衡可以表示为（i）中，其中所述p ķ是CA。7.1在25°C下。对于NH 3 CH 2 [省略图示] H 4 NO 2 -4 [省略图示] NH 2 C [省略图示] CO 2 C 6 H 4 NO 2 -4 + H +（i）和水和L和HL +的碱水解+。对于物质L，k OH = 2.3×10 2 dm 3 mol –1 s –1，k H 2 O = 6.1×10 –5 dm 3 mol –1 s –1，而对于HL +，k OH = 3.8×10 5 dm 3 mol –1 s –1和k H 2 O = 2.3×10 –6 dm 3 mol –1 s –1在35°C下。铜（II）强烈促进了酯的水解，在所采用的实验条件下，已证明金属离子的促进涉及步骤（ii）和（iii），K
• Inhibitory Effects of a Novel Water-Soluble Cyclophane on the Hydrolysis Reactions of Aromatic Esters.
  作者：Muneharu MIYAKE、Yasuo FUJIMOTO

  DOI：10.1248/cpb.42.1938

  日期：——

  The effects of a novel water-soluble cyclophane (TGCP 44, 1) on the hydrolysis reactions of aromatic esters have been studied. TGCP 44(1) was found to inhibit the hydrolysis of three aromatic esters, p-nitrophenyl chloroacetate (2), glycine p-nitrophenyl ester hydrobromide (3) and 1-nitro-2-naphthyl chloroacetate (4). The hydrolysis rates of the aromatic esters were retarded by 3.8-7.65 fold relative to the spontaneous rates.

  研究了一种新型水溶性环烷（TGCP 44，1）对芳香酯水解反应的影响。研究发现 TGCP 44(1) 可抑制三种芳香酯的水解，即对硝基苯基氯乙酸酯 (2)、甘氨酸对硝基苯基酯氢溴酸盐 (3) 和 1-硝基-2-萘基氯乙酸酯 (4)。与自发水解率相比，芳香族酯的水解率降低了 3.8-7.65 倍。