A kind of heme ligand mimetic and its synthesis method

Abstract

The invention discloses a heme ligand mimic and a synthesis method thereof. The compound name of the heme ligand mimic of the present invention is 5,10,15,20-tetra-(5-phosphophenyl)-5,10-15,20-double bundled porphyrin, and its structural formula is as formula (1) shown. The synthesis method mainly includes the following steps: dialdehyde bridging, i.e. the synthesis of the intermediate product bromo-bridged dialdehyde; ring formation, i.e. the synthesis of the intermediate product tetrabromo double-bound porphyrin; C-P bond formation, i.e. the intermediate product four Synthesis of phosphate double-bundled porphyrin; phosphate hydrolysis, that is, the synthesis of the target product tetraphosphate double-bundled porphyrin. The porphyrin of the present invention has saddle-shaped non-planar characteristics and excellent water solubility, and is a more ideal model compound for simulating the structure and function of the heme ligand; and its synthesis method has mild conditions, easy-to-obtain raw materials, fewer synthesis steps, and easy-to-use products. The purification and the yield of each step are relatively high; the introduction of phosphate not only improves the water solubility, but also widens the applicable range of pH value, and 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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