BOC-(L)-Glu(OiPr)-OH | 233692-13-2

• 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-(L)-Glu(OiPr)-OH
• 英文别名: (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-propan-2-yloxypentanoic acid
• CAS: 233692-13-2
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: ZDEMANHKGAZAOG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  BOC-(L)-Glu(OiPr)-OH 在 palladium on activated charcoal 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 3-[(S)-2-(3-{(S)-2-[3-((S)-2-Amino-4-isopropoxycarbonyl-butyrylamino)-benzoylamino]-4-isopropoxycarbonyl-butyrylamino}-benzoylamino)-4-isopropoxycarbonyl-butyrylamino]-benzoic acid
  参考文献：
  名称：

  Large Increase in Cation Binding Affinity of Artificial Cyclopeptide Receptors by an Allosteric Effect

  摘要：

  The receptor properties of a cyclopeptide composed of L-glutamic acid and 3-aminobenzoic acid in an alternating sequence are described. H-1 NMR, NOESY Nh LR. and FT-IR spectroscopic investigations show that this cyclic peptide is relatively flexible in solution. Still, it is able to bind cations by cation-pi interactions. For the n-butyltrimethylammonium iodide complex, for example, an association constant of 300 M-1 has been determined in chloroform Besides cations, the cyclopeptide is also able to bind certain anions, such as sulfonates or phosphonates, at a second binding site. Nh IR and FT-IR spectroscopic investigations show that these anions are hydrogen bonded to the peptidic NH groups. Anion complexation results in an increase of the cyclic peptide's cation affinity by a factor of 10(3)-10(4). The cyclopeptide-tosylate complex structure in solution was assigned by FT-IR, H-1 NMR, and NOESY NMR spectroscopic methods as well as molecular modeling, This structure shows that the drastic increase in cation binding affinity can be correlated with a preorganization of the cyclic peptide by the anion as well as electrostatic interactions between anion and cationic substrates in the final complex. Therefore, the influence of the anions on the complexing behavior of the cyclopeptide can be regarded as an allosteric effect. Association constants of the K+-18-crown-6, Na+-15-crown-5, and n-butyltrimethylammonium cation complexes have been determined by dilution and competitive NMR titrations.

  DOI：

  10.1021/ja983970j
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 L-glutamic acid 5-isopropyl ester 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以98%的产率得到BOC-(L)-Glu(OiPr)-OH
  参考文献：
  名称：

  Large Increase in Cation Binding Affinity of Artificial Cyclopeptide Receptors by an Allosteric Effect

  摘要：

  The receptor properties of a cyclopeptide composed of L-glutamic acid and 3-aminobenzoic acid in an alternating sequence are described. H-1 NMR, NOESY Nh LR. and FT-IR spectroscopic investigations show that this cyclic peptide is relatively flexible in solution. Still, it is able to bind cations by cation-pi interactions. For the n-butyltrimethylammonium iodide complex, for example, an association constant of 300 M-1 has been determined in chloroform Besides cations, the cyclopeptide is also able to bind certain anions, such as sulfonates or phosphonates, at a second binding site. Nh IR and FT-IR spectroscopic investigations show that these anions are hydrogen bonded to the peptidic NH groups. Anion complexation results in an increase of the cyclic peptide's cation affinity by a factor of 10(3)-10(4). The cyclopeptide-tosylate complex structure in solution was assigned by FT-IR, H-1 NMR, and NOESY NMR spectroscopic methods as well as molecular modeling, This structure shows that the drastic increase in cation binding affinity can be correlated with a preorganization of the cyclic peptide by the anion as well as electrostatic interactions between anion and cationic substrates in the final complex. Therefore, the influence of the anions on the complexing behavior of the cyclopeptide can be regarded as an allosteric effect. Association constants of the K+-18-crown-6, Na+-15-crown-5, and n-butyltrimethylammonium cation complexes have been determined by dilution and competitive NMR titrations.

  DOI：

  10.1021/ja983970j

文献信息

• Cyclic Hexapeptides with Free Carboxylate Groups as New Receptors for Monosaccharides
  作者：Joachim Bitta、Stefan Kubik

  DOI：10.1021/ol016158l

  日期：2001.8.1

  [GRAPHICS]Cyclic hexapeptides composed of alternating L-proline and 3-aminobenzoic acid subunits with substituents on the aromatic subunits that contain free carboxylate groups are able to bind monosaccharides in 4% CD3OD/CDCl3. The binding selectivity of these peptides depends on the structure of the substituents on the aromatic subunits.