Beta-cyclodextrin derivative, preparation method and application thereof

A technology for cyclodextrin and derivatives, applied in the field of cyclodextrin derivatives and their preparation, can solve the problems of low chemical activity, complex environment, harmfulness and the like, and achieve a simple preparation process, convenient post-processing and high yield. Effect

Inactive Publication Date: 2011-04-27
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the chemical activity of the second hydroxyl surface modification of cyclodextrin is not high, the previous technical route usually uses anhydrous organic solvent and strong base, which makes the post-treatment and yield of the product and a series of follow-up processes not only complicated but also difficult. harmful to the environment

Method used

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  • Beta-cyclodextrin derivative, preparation method and application thereof
  • Beta-cyclodextrin derivative, preparation method and application thereof
  • Beta-cyclodextrin derivative, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Embodiment 1 Physical measurement means and used chemical materials

[0026] The high-performance liquid chromatography used an Agilent 1200 high-performance liquid chromatography system with a UV detector, and the separation column was a Thermo Hypersil-Keystone AQUASILC18 column (4.6 mm×150 mm). The gradient elution of high performance liquid chromatography is completed within 40 minutes, and MeCN and H in the eluent 2 The ratio of O was changed linearly from 0:100 to 100:0 with a flow rate of 1.0 mL / min.

[0027] Infrared detection uses Bruker IFS66V FT-IR spectrophotometer to measure by KBr tablet method.

[0028] UV spectra were recorded with a Shimadzu UV-3100 spectrometer.

[0029] all 13 C and 1 The H-NMR spectra were all recorded on a Bruker AVANCE-500 spectrometer, the measurement temperature was 15°C, and the solvent was deuterated-dimethyl sulfoxide or heavy water.

[0030] The thermogravimetric analysis curve was recorded on the SDT-2960 thermal analyz...

Embodiment 2

[0032] Example 2 Synthesis of Intermediate 2-Ots-β-CD

[0033]β-cyclodextrin (11.5g, 10mmol) was mixed with Ts 2 O (4.9g, 15mmol) was mixed in 250ml of water, and stirred at room temperature for 2h (stirring speed was 200-400 rpm); 50ml of sodium hydroxide solution with a mass volume ratio of 10% was added, and after 1h of reaction, sand Core funnel filtration to remove unreacted Ts 2 O; add dilute hydrochloric acid solution with a concentration of about 0.5-1 mol / L to adjust to pH 3-4, and use a reduced-pressure rotary evaporation method to concentrate the solution to 50ml; control the temperature at 4°C, and cool it statically for more than 12 hours. Collect the precipitate to obtain 2-Ots - Crude β-CD; the crude product was washed with acetone and dried in vacuo to obtain the intermediate 2-Ots-β-CD as a white powder (7.4 g, 51.4%). To characterize 2-Ots-β-CD, the specific data are as follows:

[0034] Elemental analysis results: C, 42.54; H, 5.84. According to formula ...

Embodiment 3

[0039] Example 3 Synthesis of 2-Mnt-β-CD

[0040] After dissolving 3g of 2-Ots-β-CD in 5ml of water, add this solution to 10ml of an aqueous solution containing 1.2g of disodium maleicitrocyanodithionate, control the temperature at 65°C, and stir for 1 hour; cool the solution After reaching room temperature and filtering with filter paper, the filtrate was concentrated to 2-5ml by rotary evaporation under reduced pressure, and then added dropwise at a rate of 0.5 drops / second to 400ml of absolute ethanol that was vigorously stirred (stirring rate was about 500 rpm) to obtain a precipitate that was It is the crude product of 2-Mnt-β-CD; dissolve the crude product in 25ml of water, filter it through filter paper, concentrate, and then add it dropwise to 500ml of absolute ethanol with vigorous stirring (stirring rate is about 500 rpm); dropwise After standing still for more than 12 hours, the final product was precipitated from the ethanol solution; filtered through filter paper ...

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Abstract

The invention discloses a cyclodextrin derivative, a preparation method and application thereof. The cyclodextrin derivative that is mono-2-maleonitriledithiolato-beta-cyclodextrin, and a single 2-hydroxy substituted compound on a second hydroxyl surface of beat-cyclodextrin is yellow powder, is soluble in water but not ethanol, has excellent binding capacity with metallic zinc ions, and is easy to form a coordination compound with the metallic zinc ions. An aqueous solution method can be used for synthesizing an intermediate mono-2-p-toluenesulfonates and a product mono-maleonitriledithiolato-beta-cyclodextrin, with simple process, convenient post-processing and higher yield and no need of an organic solvent. A spectrum research shows that mono- maleonitriledithiolato-beta-cyclodextrin has higher binding capacity in aqueous solution and Zn 2+ion and can be used as a metallic zinc enzyme precursor so as to provide a useful precursor material for the fields of metallic zinc enzyme model compound based on the cyclodextrin chemistry and the like.

Description

technical field [0001] The present invention relates to a cyclodextrin derivative and its preparation method and application, in particular to mono-2-maleidinitriledithioene-β-cyclodextrin (2-Mnt-β-CD), the substance The preparation method and its application in the research field of metallozincase model precursor compounds. Background technique [0002] Cyclodextrin (Cyclodextrin) is a class of naturally occurring α-D-glucose macrocyclic oligomers, in which α-, β-, and γ-cyclodextrin have 6, 7, and 8 glucose structural units respectively. The diameter of the cavity is slightly different; the molecular structure includes the primary alcohol hydroxyl on the 6-position carbon atom on the first hydroxyl (primary alcohol) surface and the 2-, 3-position carbon on the second hydroxyl (secondary alcohol) surface Atoms of secondary alcoholic hydroxyl groups. Due to the hydrophilicity of their outer surface and the hydrophobicity of the cavity, cyclodextrins can include many foreig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16C12P19/04
Inventor 芦昌盛王琪王冬妮
Owner NANJING UNIV
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