Heme ligand mimic and synthesis method thereof

Abstract

The invention discloses a heme ligand mimic and a synthesis method thereof. A compound name of the heme ligand mimic provided by the invention is 5,10,15,20-tetra-(5-phenyl phosphate)-5,10-15,20-dibundled porphyrin, and a structural formula of the heme ligand mimic is as shown in a formula (1)(the formula is shown in the description). The synthesis method of the heme ligand mimic mainly comprisesthe following steps of dialdehyde bridging, namely the synthesis of an intermediate product bridged bromodialdehyde; ring formation, namely the synthesis of an intermediate product tetrabromo dibundled porphyrin; C-P bond formation, namely the synthesis of an intermediate product tetraphosphate dibundled porphyrin, and hydrolysis of phosphate, namely the synthesis of a target product tetraphosphoric acid dibundled porphyrin. Porphyrin provided by the invention has a saddle-type nonplanar feature, further, is excellent in water solubility, and is a better model compound for simulating a structure and a function of a heme ligand; further, the synthesis method of the heme ligand mimic is mild in condition and less in synthesis steps; raw materials are easily obtained; a product is easily purified; a yield in each step is relatively high, and due to the introduction of a phosphate radical, the heme ligand mimic is not only enabled to become good in water solubility and be widened in pH (potential of hydrogen) value scope of application, but also has better biological applicability.

Description

technical field [0001] The invention belongs to the research field of bioenzyme structure and function simulation, and relates to the construction of tension-containing molecules and a method for water-soluble modification of fat-soluble compounds under mild conditions, in particular to a kind of hemoglobin of a kind of bundled non-planar water-soluble porphyrin Ligand mimics and methods for their synthesis. Background technique [0002] Heme is a class of compounds that play an important role in the living body, responsible for O 2 The adsorption, storage, transportation and transformation of organic matter are closely related to life sciences. Because of the complex structure of natural heme, low content in the body, unstable configuration, and extremely high separation cost, porphyrins that conform to the structural characteristics of heme are selected or developed as ligands to simulate the structure of heme in more cases. The heme ligand model compounds are also widel...

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Problems solved by technology

[0004] One of the objectives of the present invention is to solve the deficiency that the existing heme ligand model compound macrocycle distortion and water-soluble modification cannot be satisfied at the same time, to realize the distortion of the porphyrin ring by means of bundling, and to realize the water solubility of porphyrin with the help of phosphate. To provide a non-planar water-soluble porphyrin with definite structure and configuration and excellent water solubility as a heme ligand mimic

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