α,α,α,β-5,10,15,20-tetrakis(2-β-D-glucosylphenyl)porphyrin | 124200-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: α,α,α,β-5,10,15,20-tetrakis(2-β-D-glucosylphenyl)porphyrin
• 英文别名: α,α,β,β-5,10,15,20-tetrakis(2-β-D-glucosylphenyl)porphyrin；α,β,α,β-5,10,15,20-tetrakis(2-β-D-glucosylphenyl)porphyrin
• CAS: 124200-46-0；124264-40-0；124264-41-1
• 化学式: C₆₈H₇₀N₄O₂₄
• 分子量: 1327.32
• InChiKey: WKPINVMSOKOULW-BBKGZCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  96.0
• 可旋转键数：
  16.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  454.88
• 氢给体数：
  18.0
• 氢受体数：
  26.0

反应信息

• 作为产物：
  描述：

  α,β,α,β-5,10,15,20-tetrakis<2-(2,3,4,6-tetraacetyl-β-D-glucosyl)phenyl>porphyrin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以90%的产率得到α,α,α,β-5,10,15,20-tetrakis(2-β-D-glucosylphenyl)porphyrin
  参考文献：
  名称：

  Glycoconjugated porphyrins. 2. Synthesis of sterically constrained polyglycosylated compounds derived from tetraphenylporphyrins

  摘要：

  A variety of glycoconjugated porphyrins has been synthesized by Lindsey's method from pyrrole and o-acetylglycosylated benzaldehyde precursors. Deprotection of glucose and maltose moieties allows the production of derivatives which had a good solubility in neutral aqueous solution and covered a range of amphiphilic character. The structure in solution of these new compounds was studied by H-1 NMR analysis. A study of the complexation characteristics of their zinc derivatives shows low values of affinity constants which are dependent on the steric hindrance of both faces of the porphyrin macrocycle. The present strategy should prove applicable to the synthesis of other glycoconjugated tetrapyrrolic compounds.

  DOI：

  10.1021/jo00062a020

文献信息

• Synthesis and Characterization of New Style of Water-Soluble Glycosylated Porphyrins as a Spectrophotometric Reagent for Metal Ions
  作者：Katsunori Kohata、Hisao Higashio、Yuichi Yamaguchi、Mamoru Koketsu、Tsugikatsu Odashima

  DOI：10.1246/bcsj.67.668

  日期：1994.3

  Six new styles of water-soluble glycosylated porphyrins (5, 10, 15, 20-tetrakis[2-, 3- or 4-(β-D-glucopyranosyl)phenyl]porphine) were synthesized and studied concerning their structures by 1H and 13C NMR. Tetrakis (o-substituted phenyl)porphine, consisting of four atropisomers (αβαβ, ααββ, αααβ, and αααα), was clearly assigned based on the 13C NMR peak-splitting pattern. It was especially noteworthy

  合成了六种新型水溶性糖基化卟啉（5、10、15、20-四[2-、3-或4-（β-D-吡喃葡萄糖基）苯基]卟啉），并通过1H和13C研究了它们的结构核磁共振。Tetrakis（邻取代苯基）卟啉由四种阻转异构体（αβαβ、ααββ、αααβ 和 αααα）组成，根据 13C NMR 峰分裂模式明确指定。特别值得注意的是，获得了水溶性栅栏卟啉（αααα）。此外，研究了它们作为金属离子显色试剂的特性。高度水溶性葡萄糖的引入成功地改善了迄今为止制备的阴离子或阳离子卟啉的聚集和吸附特性，而其他重要的分析特性没有任何显着变化。
• Glycoconjugated tetrapyrrolic macrocycles
  作者：Philippe Maillard、Serge Gaspard、Jean Luc Guerquin-Kern、Michel Momenteau

  DOI：10.1021/ja00207a033

  日期：1989.12

  Preparation de porphyrine ou de phtalocyanine metalliques substituees par le glucose a partir de la condensation du tetraacetyl β-D-glucose-2 benzaldehyde avec le pyrrole

  制备卟啉或酞菁金属替代物与葡萄糖和四乙酰基 β-D-葡萄糖-2 苯甲醛 avec le 吡咯的缩合
• Porphyrin Synthesis in Surfactant Solution:  Multicomponent Assembly in Micelles
  作者：Richard P. Bonar-Law

  DOI：10.1021/jo9600161

  日期：1996.1.1

  A synthesis of meso-substituted porphyrins in anionic sodium dodecyl sulfate micelles has been developed. Polar, functionalized aromatic aldehydes condense reversibly with pyrrole in the micellar phase. Oxidation of the porphyrinogen then provides functionalized porphyrins in yields of 10-48%. Hydrophobic aldehydes condense irreversibly to give low yields at practical substrate concentrations. Synthesis in D2O solution results in per-beta-deuterated porphyrins. A two-phase model is used to rationalize the dependence of porphyrin yield on reactant and surfactant concentration. Micelles are viewed as potential wells which promote porphyrinogen assembly by binding products more tightly than reactants.