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Preparation method of mono-sulfonated Lewis trisaccharide

A single sulfonic and sugar component technology, applied in the preparation of sugar derivatives, chemical instruments and methods, oligosaccharides, etc., can solve the problems of time-consuming and laborious, and achieve the effect of simple preparation method and strong controllability of reaction conditions

Pending Publication Date: 2017-12-29
FOSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These syntheses are really time-consuming and laborious, and it is necessary to find a more efficient way to generate sulfonic acid oligosaccharides

Method used

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  • Preparation method of mono-sulfonated Lewis trisaccharide

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preparation example Construction

[0017] A preparation method for monosulfonated Lewis trisaccharides, comprising the steps of:

[0018] 1) 300~350mg of 0.3mmol / L 8-p-methoxyphenoxyoctyl 2-acetamido 3-O-(b-D-galactopyranoside) 4-O-(2,3,4 -Tri-O-benzyl a-L-fucopyranoside) 2-deoxy-b-D-glucopyranoside was dissolved in 3~5mL of anhydrous pyridine, and then 85~100mg of 0.6mmol / L sulfur trioxide pyridine was added For the complex compound, mix and stir at 78-82°C for 14-15.5 hours, add toluene, evaporate the co-solvent, and obtain the original residue;

[0019] 2) Dissolving the original residue obtained in step 1) in a mixed solvent of 4 to 5 mL of methanol and acidic acid, adding a palladium or carbon catalyst, stirring at room temperature containing hydrogen for 25 to 32 hours, removing the catalyst and the mixed solvent to obtain a residue;

[0020] 3) Put the residue obtained in step 2) into a DEAE-Sephadex A-50 column, elute with water to remove sulfated sugars, and elute monosulfated sugars with 5% NaCl solu...

Embodiment approach

[0023] As a further embodiment, the preparation method includes the following steps:

[0024] 1) 320 mg of 0.3 mmol / L 8-p-methoxyphenoxyoctyl 2-acetylamino 3-O-(b-D-galactopyranoside) 4-O-(2,3,4-tri -O-benzyl a-L-fucopyranoside) 2-deoxy-b-D-glucopyranoside was dissolved in 3mL of anhydrous pyridine, then added 95mg of 0.6mmol / L sulfur trioxide pyridine complex, at 80 Mix and stir for 15 h at ℃, add toluene, evaporate the co-solvent, and obtain the original residue;

[0025] 2) dissolving the original residue obtained in step 1) in a mixed solvent of 4 mL of methanol and acidic acid, adding a palladium or carbon catalyst, stirring for 30 h at room temperature containing hydrogen, removing the catalyst and mixed solvent to obtain a residue;

[0026] 3) Put the residue obtained in step 2) into a DEAE-Sephadex A-50 column, elute with water to remove sulfated sugars, and elute monosulfated sugars with 5% NaCl solution and 15% NaCl solution respectively. sugar components and sulfa...

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Abstract

The invention discloses a preparation method of mono-sulfonated Lewis trisaccharide. The preparation method of the mono-sulfonated Lewis trisaccharide comprises the following steps: (1) dissolving 300-350 mg of 8-p-methoxy-benzeneoctanoxy 2-acetamido 3-O-(b-D-galactopyranoside) 4-O-(2, 3, 4-tri-O-benzyl a-L-fucopyranoside) 2-deoxidation-b-D-glucopyranoside 0.3 mmol / L in 3-5 mL of anhydrous pyridine, then adding 85-100 mg of a sulfur trioxide pyridine complex 0.6 mmol / L, mixing and stirring for 14-15.5 hours at the temperature of 78-82 DEG C, adding methylbenzene, and evaporating a cosolvent to obtain original residues; (2) dissolving the original residues in 4-5 mL of a mixed solvent of methanol and acid, adding a palladium or carbon catalyst, stirring for 25-32 hours at the room temperature under the condition that hydrogen exists, and removing the catalyst and the mixed solvent to obtain residues; (3) placing the residues in DEAE-Sephadex A-50 columns, removing sulfated saccharide by elution with water, and eluting a mono-sulfonatedsaccharide component and a sulfated saccharide component by using a NaCl solution with the molar concentration of 5% and a NaCl solution with the molar concentration of 15% separately; and (4) loading residues obtained after a mono-sulfonated fraction is desolventized on C-18 columns, eluting the residues with water and then washing the residues with methanol to obtain the mono-sulfonated Lewis trisaccharide. The preparation method is the most effective method for generating sulfonic acid oligosaccharideuntil now.

Description

technical field [0001] The invention relates to the field of polymer synthesis, in particular to a method for preparing monosulfonated Lewis trisaccharides. Background technique [0002] The biological significance of polysaccharides has the activity of stimulating the synthesis of oligosaccharides, but the procedure of oligosaccharide synthesis is cumbersome and expensive. A combinatorial approach provides a feasible solution to this problem of oligosaccharide synthesis. [0003] Sulfonate groups have been shown to be persistently involved in selectin-ligand interactions, therefore, a combinatorial approach to the synthesis of sulfo-oligosaccharide libraries may be useful for the screening of selectin ligands. By using different protecting groups, heparin-related sulfonated disaccharides were synthesized from a library of sulfo-oligosaccharides 48 , utilizing orthogonally removable protecting groups, 16 chondroitin sulfate-related sulfonated disaccharides were generated wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/06C07H1/00
CPCC07H1/00C07H3/06
Inventor 丁毅力高树华王丙云陈胜峰王少杰李紫元
Owner FOSHAN UNIVERSITY
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