A method for preparing mannuronic acid monomers by degrading polymannuronic acid with sulfuric acid

A technology of polymannuronic acid and mannuronic acid, which is applied in the field of sulfuric acid degradation of polymannuronic acid to prepare mannuronic acid monomer, can solve the problems of high price, achieve short time-consuming, high practicability, and degradation Conditions and effects of simple operation

Active Publication Date: 2022-04-08
QINGDAO BZ OLIGO BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The patent "CN201310028146.2 A method for preparing alginic acid oligosaccharide monomers by microwave radiation" discloses a method for microwave degradation of polymannuronic acid, but only mannuronic acid with a degree of polymerization of 1-9 is prepared in this method Acid oligosaccharide monomer, and microwave digestion instrument is not commonly used experimental equipment, expensive
At present, the one-time preparation of mannuronic acid oligosaccharide monomers with a polymerization degree of 1-10 is still blank

Method used

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  • A method for preparing mannuronic acid monomers by degrading polymannuronic acid with sulfuric acid
  • A method for preparing mannuronic acid monomers by degrading polymannuronic acid with sulfuric acid
  • A method for preparing mannuronic acid monomers by degrading polymannuronic acid with sulfuric acid

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Effect test

Embodiment 1

[0047] A method for preparing mannuronic acid monomers by degrading polymannuronic acid with sulfuric acid, comprising the following steps:

[0048] (1) Degradation of polymannuronic acid

[0049] Weigh 6g of polymannuronic acid sodium in a three-necked bottle, add 300mL concentration of 2mol / L sulfuric acid solution to prepare a 20g / L polymannuronic acid sulfuric acid degradation system, and stir at room temperature to make polymannuronic acid fully Dissolve; then stir in a water bath at 80°C for 4 hours; after the reaction, add anhydrous calcium carbonate powder to remove sulfate groups, filter, adjust the pH of the filtrate to neutral with NaOH solution, concentrate to obtain the oligosaccharide mixture; freeze-dry the concentrated oligosaccharide mixture;

[0050] (2) Preparation of oligosaccharide mixture solution and mobile phase

[0051] a, the preparation of oligosaccharide solution: take this oligosaccharide mixture, use 0.5mol / L NH 4 HCO 3 The solution was made in...

Embodiment 2

[0057] Example 2 Purity Determination

[0058] The mannuronic acid monomers with different degrees of polymerization obtained after freeze-drying were tested by HPLC and MS to determine their purity.

[0059] (1) Pre-column derivation high performance liquid chromatography (HPLC) analysis

[0060] Detection instrument: Dionex UltiMate 3000 liquid chromatograph; Chromatographic column: Kromasil C18 (4.6mm×150mm, 5μm); Mobile phase: Phosphate buffer / acetonitrile (83:17, V / V);

[0061] (2) Electrospray mass spectrometry (ESI-MS) analysis

[0062] Detection instrument: American Micromass Q-TOF Ultima Global quadrupole time-of-flight tandem mass spectrometer; mass spectrometry detection conditions: negative ion detection mode;

[0063] The test results are shown in Figure 2-11. Both the mass spectrogram and the liquid phase chromatogram present a single peak, and the peak shape is symmetrical. The calculated purity of mannuronic acid M1-M10 is above 95%.

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Abstract

The invention discloses a method for preparing mannuronic acid monomer by degrading polymannuronic acid with sulfuric acid. Bio-Gel P10fine or Bio-Gel P6fine gel permeation chromatography is used to separate and purify the degraded oligosaccharide mixture to obtain 10 oligosaccharide components; use thin layer chromatography (TLC), high performance liquid chromatography (HPLC), mass spectrometry (MS) to analyze different components, and prepare mannuronic acid oligosaccharides with a polymerization degree of 1‑10 monomer. The method of the present invention can prepare mannuronic acid oligosaccharide monomers with a degree of polymerization of 1-10, and the purity reaches more than 95%. At the same time, the method uses sulfuric acid as the degradation condition, and anhydrous calcium carbonate is added after degradation, and after stirring and filtering Sulfate ions can be removed directly to avoid secondary desalination during purification. The method is time-consuming, simple and easy to operate, and can be separated and purified in large quantities with good repeatability.

Description

technical field [0001] The invention relates to a method for preparing mannuronic acid monomers by degrading polymannuronic acid with sulfuric acid, and belongs to the technical field of seaweed oligosaccharide extraction. Background technique [0002] Alginate is a kind of intercellular polysaccharide extracted and isolated from marine brown algae. A block compound composed of glycosidic linkages. There are mainly three structural fragments in the alginate molecule: β-D-(1,4)-linked polymannuronic acid (Polmannuronate, PM); α-L-(1,4)-linked polygulose Alkyd acid (Poiyguluronate, PG); G and M alternately copolymerized segment PMG. In recent years, important progress has been made in the research on the biological activity of PM, especially in anti-tumor, growth-promoting and anti-senile dementia research. However, its relative molecular mass (Mr) is relatively large, which limits its application. The mannuronic acid oligosaccharides prepared by various degradation method...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/04C13K13/00
CPCC13K13/00C08B37/0003C08B37/0084
Inventor 岳帆赵峡张斌管昶王丽丽高芹芹
Owner QINGDAO BZ OLIGO BIOTECH
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