Synthesis and application of novel cyclodextrin polymer chiral resolving agents

A technology of cyclodextrin polymer and cyclodextrin, which is applied in the direction of electrogenesis process, electrolysis process, etc., can solve the problem of high ion strength of charged CDs derivatives, high ion strength of charged cyclodextrin derivatives, degree of substitution and substitution position Difficult to control and other problems, to achieve good economic value and application prospects, convenient polymer purification treatment, strong chiral resolution effect

Inactive Publication Date: 2013-02-13
TIANJIN AOSHUNDA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of the above-mentioned prior art, the present invention provides a new synthesis idea to obtain a derivatized cyclodextrin chiral resolution agent with uniform substitution position and degree of substitution, and link the derivatized cyclodextrin with uneven substitution into a polymer, thereby Effectively solve the problem of difficult uniformity of substitution degree, low water solubility of natural cyclodextrin, high ion strength of charged cyclodextrin derivatives, poor batch repeatability of synthetic products, peak broadening and other problems, with simple synthesis method and few steps, Advantages such as low synthesis cost
[0010] (1) Taking the preparation of charged cyclodextrin polymer as an example to illustrate the design idea of ​​a new chiral resolving agent to solve the problem of low water solubility of natural cyclodextrin (such as β-CD cyclodextrin) and high ionic strength of charged CDs derivatives , degree of substitution and substitution position are difficult to control, expensive and other problems

Method used

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  • Synthesis and application of novel cyclodextrin polymer chiral resolving agents
  • Synthesis and application of novel cyclodextrin polymer chiral resolving agents
  • Synthesis and application of novel cyclodextrin polymer chiral resolving agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Synthesis of SPE-β-CDP according to the reaction steps of first sulfonation and then polymerization

[0057] 9 g of recrystallized β-CD was slowly added to 20 mL of 20% (w / v) NaOH solution. After stirring at room temperature for 1 h, 4.2 mL of 1,3-propane sultone (1,3-PS) was slowly added dropwise, and the mixture was reacted at 75° C. for 3 h. After stopping the reaction, cool to room temperature, neutralize to neutral with 6 mol / L HCl, concentrate the reaction solution and dry to obtain 11.58 g of light yellow solid SPE-β-CD with a yield of 87.67%.

[0058] 4g of the above-mentioned sulfopropyl ether β-cyclodextrin was dissolved in 4mL of 30% (w / v) NaOH solution, and stirred for 0.5h until completely dissolved. Add 2 mL of epichlorohydrin (Ep), keep stirring rapidly, stop the reaction after reacting at 75 °C for 3 h, cool to room temperature, neutralize with 6 mol / L HCl, pour into a dialysis bag with a molecular cut-off of 7000, and remove Dialyze in deio...

Embodiment 2

[0059] Example 2: Synthesis of SPE-α-CDP according to the reaction steps of first sulfonation and then polymerization

[0060] Weigh 3.0000g α-cyclodextrin into a round bottom flask, add 6.0mL 20% (w / v) NaOH solution, stir and dissolve at room temperature for 0.5h, add 2.6mL 1,3-PS, react at 75°C for 3h After the reaction is complete, cool to room temperature and adjust the pH to neutral with dilute HCl. The concentrated reaction solution was dried to obtain 6.2162 g of light yellow solid SPE-α-CD.

[0061] Weigh 3.0064g of sulfopropyl ether α-cyclodextrin monomer into a round bottom flask, add 6.0mL of 30% (w / v) NaOH solution, stir and dissolve at room temperature for 0.5h, add 4mL of Ep, at 75°C After reacting for 3 h, the reaction was cooled to room temperature, and the pH was adjusted to neutral with dilute HCl. Dialysis was performed with a dialysis membrane with a molecular cut-off of 7000 to remove unreacted monomers, and the dialysate was concentrated and dried by ro...

Embodiment 3

[0062] Example 3: Synthesis of SPE-γ-CDP with different degrees of polymerization according to the reaction steps of first sulfonation and then polymerization

[0063] Weigh 10g of γ-CD and slowly add it into 20mL of 20% (w / v) NaOH solution. After stirring at room temperature for 0.5 h, 7.7 mL of 1,3-PS was slowly added dropwise, and the mixture was reacted at 75° C. for 3 h. Cool down after stopping the reaction, neutralize with 6 mol / L HCl, concentrate the reaction solution and dry to obtain 20.9536 g of light yellow solid SPE-γ-CD.

[0064] Then synthesize the following SPE-γ-CDP with different degrees of polymerization:

[0065] (1) 2.0057g of the above SPE-γ-CD was dissolved in 1.8mL of 30% (w / v) NaOH solution, stirred for 0.5h until completely dissolved. Add 0.6mL (5eq) Ep, keep stirring rapidly, stop the reaction at 75°C for 3h, cool to room temperature, neutralize with 6mol / L HCl, pour into a dialysis bag with a molecular weight cut off of 7000, and dialyze in deioni...

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Abstract

The invention discloses novel sulfopropyl ether ring dextrin polymers and a synthesis method thereof. Derived cyclodextrins with nonuniform substitution degree are connected into a polymer, and the cyclodextrins are sulfonated and polymerized to obtain the derived cyclodextrin chiral resolving agents with uniform substitution position and substitution degree. The characterization on the three novel sulfopropyl ether ring dextrin polymers (sulfopropyl ether alpha-CD (cyclodextrin) polymer, sulfopropyl ether beta-CD polymer and sulfopropyl ether gamma-CD polymer) proves the advantages of the design concept; and the polymers can be respectively used as a buffer additive for separating capillary electrophoresis chiral compounds. The invention can solve the problems of low water solubility, high ionic strength of charged cyclodextrin derivatives, poor batch repetitiveness of synthesized products, wide peak range and the like, and has the advantages of simple synthesis method, fewer steps, low synthesis cost and the like.

Description

technical field [0001] The present invention relates to a new class of chiral resolving agent—the synthesis method and application of sulfopropyl ether α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin polymers. Such polymers can be used as chiral The resolving agent is added to the running buffer of capillary electrophoresis for the separation of chiral compounds in capillary electrophoresis. It has high water solubility, good statistical uniformity in the degree of substitution of sulfonated functional groups and substitution positions, high efficiency, economy, and recyclability. Utilization and other characteristics are conducive to industrialized large-scale use, and have good economic value and application prospects. Background technique [0002] Among the synthetic drugs on the market, there are very few single enantiomer drugs. With the development of chiral selection technology, the proportion of pure enantiomer drugs with high pharmacological effects in synthetic d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/28C25B7/00
Inventor 包建民李优鑫贾菲菲梁清刚王雨潇
Owner TIANJIN AOSHUNDA TECH CO LTD
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