Heme ligand mimic and synthesis method thereof

A synthetic method and heme technology, applied in the research field of biological enzyme structure and function simulation, to achieve good water solubility and biocompatibility, low reaction cost, and easy purification

Active Publication Date: 2019-05-28
HUNAN UNIV OF SCI & TECH
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 porp

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Heme ligand mimic and synthesis method thereof
  • Heme ligand mimic and synthesis method thereof
  • Heme ligand mimic and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0052] The present invention will be further described in detail below in conjunction with specific experimental examples.

[0053] Phosphorylated water-soluble porphyrin of the present invention, its compound name is 5,10,15,20-tetrakis-(5-phosphophenyl)-5,10-15,20-double bundled porphyrin, and its compound structural formula is as follows: (1) as shown:

[0054]

[0055] Its compound synthetic train of thought route is as shown in formula (5):

[0056]

[0057] As can be seen from the formula (5), its specific synthesis steps are completed in four steps.

[0058] The first step is the bridging of the strapping chain. Use 50ml of DMF as a solvent, heat to a constant temperature of 65°C, add 20g (ie 0.10mol) of 5-bromosalicylaldehyde and 28g (ie 0.2mol, 2 equivalents) of anhydrous potassium carbonate, and keep it for about 10 minutes; 10g of 3-dibromopropane (ie 0.05mol, 0.5 equivalent) was added dropwise to the DMF reaction solution within 20min, continued to keep th...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07F9/6527
Inventor 周再春杨艳唐敏刘秋华
Owner HUNAN UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap