Boc-PGG-OCH2Ph | 31953-81-8

• 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: Boc-PGG-OCH2Ph
• 英文别名: tert-butyl (2S)-2-[[2-oxo-2-[(2-oxo-2-phenylmethoxyethyl)amino]ethyl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 31953-81-8
• 化学式: C₂₁H₂₉N₃O₆
• 分子量: 419.478
• InChiKey: JDRKNLFAGGHYHQ-INIZCTEOSA-N

物化性质

• 沸点：
  641.6±55.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Boc-PGG-OCH2Ph 在 盐酸 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 {2-[(1-{2-[2-(2-dioctadecylcarbamoylmethoxyacetylamino)acetylamino]acetyl}pyrrolidine-2-carbonyl)amino]acetylamino}acetic acid benzyl ester
  参考文献：
  名称：

  Cation Dependence of Chloride Ion Complexation by Open-Chained Receptor Molecules in Chloroform Solution

  摘要：

  Seventeen peptides, most having the sequence GGGPGGG, but differing in the C- and N-terminal ends, have been studied as anion-complexing agents. These relatively simple, open-chained peptide systems interact with both chloride and the associated cation. Changes, in the N- and C-terminal side chains appear to make little difference in the efficacy of binding. NMR studies suggest that the primary interactions involve amide NH contacts with the chloride anion, and CD spectral analyses suggest a concomitant conformational change upon binding. Changes in binding constants, which are expected in different solvents, also suggest selective solvent interactions with the unbound host that helps to preorganize the open-chained peptide system. Significant differences are apparent in complexation strengths when the heptapeptide chain is shortened or lengthened or when the relative position of proline within the heptapeptide is varied.

  DOI：

  10.1021/ja0558894
• 作为产物：
  描述：

  苯甲醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 57.0h， 生成 Boc-PGG-OCH2Ph
  参考文献：
  名称：

  Cation Dependence of Chloride Ion Complexation by Open-Chained Receptor Molecules in Chloroform Solution

  摘要：

  Seventeen peptides, most having the sequence GGGPGGG, but differing in the C- and N-terminal ends, have been studied as anion-complexing agents. These relatively simple, open-chained peptide systems interact with both chloride and the associated cation. Changes, in the N- and C-terminal side chains appear to make little difference in the efficacy of binding. NMR studies suggest that the primary interactions involve amide NH contacts with the chloride anion, and CD spectral analyses suggest a concomitant conformational change upon binding. Changes in binding constants, which are expected in different solvents, also suggest selective solvent interactions with the unbound host that helps to preorganize the open-chained peptide system. Significant differences are apparent in complexation strengths when the heptapeptide chain is shortened or lengthened or when the relative position of proline within the heptapeptide is varied.

  DOI：

  10.1021/ja0558894

文献信息

• Fluorescent, Synthetic Amphiphilic Heptapeptide Anion Transporters: Evidence for Self‐Assembly and Membrane Localization in Liposomes
  作者：Lei You、George W. Gokel

  DOI：10.1002/chem.200800147

  日期：2008.6.27

  Synthetic anion transporters (SATs) of the general type (n-C18H37)2N-COCH2OCH2CO-(Gly)3-Pro-(Gly)3-O-n-C7H15, 1, are amphiphilic peptides that form anion-conducting pores in bilayer membranes. To better understand membrane insertion, assembly and aggregation dynamics, and membrane penetration, four novel fluorescent structures were prepared for use in both aqueous buffer and phospholipid bilayers.

  一般类型 (n-C18H37)2N-COCH2OCH2CO-(Gly)3-Pro-(Gly)3-On-C7H15, 1 的合成阴离子转运蛋白 (SAT) 是两亲性肽，在双层膜中形成阴离子传导孔。为了更好地了解膜插入、组装和聚集动力学以及膜渗透，制备了四种新型荧光结构，用于水性缓冲液和磷脂双层。将荧光残基芘、吲哚、丹酰基和NBD掺入1中，分别得到2、3、4和5。通过监测 2 观察到的芘单体/准分子峰的变化，证实了缓冲液中肽两亲物的组装。双层中吲哚 (3) 和丹磺酰 (4) 侧链 SAT 观察到的溶剂依赖性荧光变化表明，这些残基经历了极性介于 epsilon=9 (CH2Cl2) 和 epsilon=24 (EtOH) 之间的环境。 2 和 3 之间的荧光共振能量转移 (FRET) 表明 SAT 单体在双层内聚集。这种自组装导致孔的形成，这被检测为 Cl(-) 从脂质体中释放。荧光 SAT 的丙烯酰胺猝灭结果支持膜插入。
• Anokhina, V. V.; Sorochinskaya, E. I.; Golubovich, V. P., Journal of general chemistry of the USSR, 1990, vol. 60, # 1.2, p. 178 - 184
  作者：Anokhina, V. V.、Sorochinskaya, E. I.、Golubovich, V. P.、Kinarskii, L. I.、Martynov, V. F.

  DOI：——

  日期：——
• ANOXINA, V. V.;SOROCHINSKAYA, E. I.;GOLUBOVICH, V. P.;KIRNARSKIJ, L. I.;M+, ZH. OBSHCH. XIMII, 60,(1990) N, S. 203-211
  作者：ANOXINA, V. V.、SOROCHINSKAYA, E. I.、GOLUBOVICH, V. P.、KIRNARSKIJ, L. I.、M+

  DOI：——

  日期：——