N.N'-(N-benzyloxycarbonyl-L-glutamoyl)-bis-L-glutamic acid tetraethyl ester | 65148-67-6

• 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: N.N'-(N-benzyloxycarbonyl-L-glutamoyl)-bis-L-glutamic acid tetraethyl ester
• 英文别名: N.N'-(N-Benzyloxycarbonyl-L-glutamoyl)-bis-L-glutaminsaeure-tetraaethylester；Cbz-Glu(1)-Glu(OEt)-OEt.N(1)Glu(OEt)-OEt；diethyl (2S)-2-[[(4S)-5-[[(2S)-1,5-diethoxy-1,5-dioxopentan-2-yl]amino]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanedioate
• CAS: 65148-67-6
• 化学式: C₃₁H₄₅N₃O₁₂
• 分子量: 651.711
• InChiKey: WTQJXUOMVGIYFV-HJOGWXRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  46
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N.N'-(N-benzyloxycarbonyl-L-glutamoyl)-bis-L-glutamic acid tetraethyl ester 在 palladium on activated charcoal 氢气 、 ammonium formate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以88%的产率得到Tetraethyl-α,γ-bis-(L-Glutamyl-L-glutamat)
  参考文献：
  名称：

  The synthesis of immobilised chiral dendrimers

  摘要：

  对氨基酸手性树枝状聚合物的一锅合成方法表明，具有肽链的树枝状聚合物产量很高。利用这种合成策略，可以改变外围功能，也可以取代其他氨基酸，得到混合氨基酸树枝状聚合物。我们的树枝状聚合物是通过羧基衍生树枝状聚合物与氨基丙基改性二氧化硅的偶联方法实现固定化的。在一锅程序中使用 2-乙氧基-1-乙氧基-1,2-二氢喹啉可改善反应条件，从而获得含有大量树枝状聚合物的二氧化硅。固态核磁共振分析证实，树枝状聚合物与二氧化硅结合在一起，而且看起来结构完整。这些固定的手性树枝状聚合物构成了用于高效液相色谱的新型手性固定相。

  DOI：

  10.1039/b008597i
• 作为产物：
  描述：

  L-谷氨酸 在 4-二甲氨基吡啶 、 碳酸氢钠 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 N.N'-(N-benzyloxycarbonyl-L-glutamoyl)-bis-L-glutamic acid tetraethyl ester
  参考文献：
  名称：

  Twyman, L. J.; Beezer, A. E.; Esfand, R., Journal of Chemical Research, Miniprint, 1998, # 12, p. 3408 - 3460

  摘要：

  DOI：

文献信息

• The synthesis of immobilised chiral dendrimers
  作者：B. T. Mathews、A. E. Beezer、M. J. Snowden、M. J. Hardy、J. C. Mitchell

  DOI：10.1039/b008597i

  日期：——

  A one pot synthetic approach to amino acid based chiral dendrimers was shown to give good yields for dendrimers with peptide linkages. Using this synthetic strategy, modification of the peripheral functionality is possible, as is the substitution of other amino acids to give mixed amino acid based dendrimers. Immobilization of our dendrimers was accomplished using a coupling method involving the carboxy derivatised dendrimers with an aminopropyl modified silica. The use of 2-ethoxy-1-ethoxy-1,2-dihydroquinoline in a one pot protocol gave enhanced reaction conditions from which silicas bearing very high levels of dendrimer were obtained. Solid state NMR analysis substantiated that the dendrimers were bound to the silica and that they appeared to be structurally intact. These immobilised chiral dendrimers constitute a new class of chiral stationary phases for use in HPLC.

  对氨基酸手性树枝状聚合物的一锅合成方法表明，具有肽链的树枝状聚合物产量很高。利用这种合成策略，可以改变外围功能，也可以取代其他氨基酸，得到混合氨基酸树枝状聚合物。我们的树枝状聚合物是通过羧基衍生树枝状聚合物与氨基丙基改性二氧化硅的偶联方法实现固定化的。在一锅程序中使用 2-乙氧基-1-乙氧基-1,2-二氢喹啉可改善反应条件，从而获得含有大量树枝状聚合物的二氧化硅。固态核磁共振分析证实，树枝状聚合物与二氧化硅结合在一起，而且看起来结构完整。这些固定的手性树枝状聚合物构成了用于高效液相色谱的新型手性固定相。
• Methotrexate analogs. 10. Direct coupling of methotrexate and diethyl L-glutamate in the presence of peptide bond-forming reagents
  作者：Andre Rosowsky、Cheng-Sein Yu

  DOI：10.1021/jm00200a005

  日期：1978.2
• Dendrimers with tetrabenzoporphyrin cores: near infrared phosphors for in vivo oxygen imaging
  作者：Ivo B Rietveld、Evelyn Kim、Sergei A Vinogradov

  DOI：10.1016/s0040-4020(03)00432-0

  日期：2003.5

  Pd complexes of tetrabenzoporphyrins (PdTBPs) are strong near infra-red phosphors, suitable for tissue oxygen imaging by phosphorescence quenching. For in vivo use, PdTBP phosphors have to be water-soluble and protected from interactions with biomacromolecules in the blood. An approach to the construction of biologically compatible PdTBP-phosphors based on dendritic encapsulation is proposed. A series of polyglutamic PdTBP-dendrimers was synthesized and their optical and quenching properties were studied. While retaining the excellent optical characteristics (lambda(max) (Q)=630 nm, phi(phos)=12%) of basic PdTBPs and in addition being highly water soluble. PdTBP-dendrimers still exhibit excessively high oxygen quenching constants (2000-3000 mmHg(-1)s(-1)) and form complexes with lipophilic proteins, such as serum albumin. Modification of the dendrimer periphery with polyethyleneglycol chains somewhat reduces the quenching constants but does not prevent binding of the phosphors to albumin. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Porphyrin and Tetrabenzoporphyrin Dendrimers:  Tunable Membrane-Impermeable Fluorescent pH Nanosensors
  作者：Olga Finikova、Alexander Galkin、Vladimir Rozhkov、Maria Cordero、Cecilia Hägerhäll、Sergei Vinogradov

  DOI：10.1021/ja0341687

  日期：2003.4.1

  The pH dependencies of the UV-vis and fluorescent spectra of new water-soluble dendritic porphyrins and tetrabenzoporphyrins were studied. Because of extended pi-conjugation and nonplanar distortion, the absorption and the emission bands of tetraaryltetrabenzoporphyrins (Ar4TBP) are red-shifted and do not overlap with those of regular tetraarylporphyrins (Ar4P). When encapsulated inside dendrimers with hydrophilic outer layers, Ar(4)Ps and Ar(4)TBPs become water soluble and can serve as pH indicators, with pKs adjustable by the peripheral charges on the dendrimers. Two new dendritic porphyrins, Gen 4 polyglutamic porphyrin dendrimer H2P-Glu(4)OH (1) with 64 peripheral carboxylates and Gen 1 poly(ester amide) Newkome-type tetrabenzoporphyrin dendrimer H2TBP-Nw(1)OH (2) with 36 peripheral carboxylates, were synthesized and characterized. The pKs of the encapsulated porphyrins (pK(H2P-Glu)(OH)(4) = 6.2 and pK(H2TBP)-Nw(1)OH = 6.3) were found to be strongly influenced by the dendrimers, revealing significant electrostatic shielding of the cores by the peripheral charges. The titration curves obtained by differential excitation using the mixtures of the dendrimers were shown to be identical to those determined for the dendrimers individually. Due to their peripheral carboxylates and nanometric molecular size, porphyrin dendrimers cannot penetrate through phospholipid membranes. Dendrimer 1 was captured inside phospholipid liposomes, which were suspended in a solution containing dendrimer 2. No response from 1 was detected upon pH changes in the bulk solution, while the response from 2 was predictably strong. When proton channels were created in the liposome walls, both compounds responded equally to the bulk pH changes. These results suggest that porphyrin dendrimers can be used as fluorescent pH indicators for proton gradient measurements.
• Pteroic Acid Derivatives. I. Pteroyl-α-glutamylglutamic Acid and Pteroyl-α,γ-glutamyldiglutamic Acid
  作者：J. H. Mowat、B. L. Hutchings、R. B. Angier、E. L. R. Stokstad、J. H. Boothe、C. W. Waller、J. Semb、Y. Subba Row

  DOI：10.1021/ja01183a067

  日期：1948.3