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Straight-chain oligosaccharide library and preparation method thereof

An oligosaccharide and straight-chain technology, applied in the field of straight-chain oligosaccharide library and preparation thereof, can solve the problems of time-consuming and laborious, complex oligosaccharide synthesis method, etc., and achieve the effects of low price, few synthesis steps, and easy availability.

Inactive Publication Date: 2014-06-04
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a linear oligosaccharide library with few synthesis steps and simple operation and its preparation method in view of the defects of the existing oligosaccharide synthesis method, which are relatively complicated, time-consuming and labor-intensive.

Method used

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  • Straight-chain oligosaccharide library and preparation method thereof
  • Straight-chain oligosaccharide library and preparation method thereof
  • Straight-chain oligosaccharide library and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Add triphenylphosphine and halohydrocarbon with a molar ratio of 1:1.2 into the container, dissolve in 50mL organic solvent under nitrogen protection, stir for 6h to generate dichlorotriphenylphosphine and then add 1 equivalent of . The D-ribose was dehydrated in a vacuum, and stirred for 72 hours in an ice-water bath. Add 30mL of water after distilling off THF under reduced pressure, stir in an ice-water bath for 1 hour, and then filter under reduced pressure. Oligosaccharide library of ribose. Using ESI-MS n Identify the generation of the oligosaccharide library, and use multi-stage mass spectrometry to identify the structure of each oligosaccharide. The relevant mass spectrometry results are as follows: Figure 1~6 shown. The structures of various oligosaccharide products in the library and the corresponding mass-to-charge ratios detected by mass spectrometry are shown below:

[0052]

[0053] Ribose dimer [Disaccharide+Cl] - :317.06m / z

[0054]

[0055] Ri...

Embodiment 2

[0063] Dissolve triphenylphosphine and halogenated hydrocarbons with a molar ratio of 1:1.2 in 50 mL of organic solvent under the protection of nitrogen, stir for 6 hours, and add 1 equivalent of D-xylose under nitrogen atmosphere to generate dihalotriphenylphosphine , and stirred for 72h under ice-water bath conditions. Add 30mL of water after distilling off THF under reduced pressure, stir in an ice-water bath for 1 hour, and then filter under reduced pressure. Oligosaccharide library of xylose. Using ESI-MS n Identify the generation of the oligosaccharide library, and use multi-stage mass spectrometry to identify the structure of each oligosaccharide. The relevant mass spectrometry results are as follows: Figure 7-12 shown. The structures of various oligosaccharide products in the library and the corresponding mass-to-charge ratios detected by mass spectrometry are shown below:

[0064]

[0065] Xylose dimer [Disaccharide+Cl] - :317.06m / z

[0066]

[0067] Xylo...

Embodiment 3

[0075] Dissolve triphenylphosphine and halogenated hydrocarbons with a molar ratio of 1:1.2 in 50 mL of organic solvent under nitrogen protection, stir for 6 h, and add 1 equivalent of D-glucose under nitrogen atmosphere after generating dihalotriphenylphosphine. It was stirred for 72h under the condition of ice-water bath. Add 30mL of water after distilling off THF under reduced pressure, stir in an ice-water bath for 1 hour, and then filter under reduced pressure. Oligosaccharide library of glucose. Using ESI-MS n Identify the generation of the oligosaccharide library, and use multi-stage mass spectrometry to identify the structure of each oligosaccharide. The relevant mass spectrometry results are as follows: Figure 13~17 shown. The structures of various oligosaccharide products in the library and the corresponding mass-to-charge ratios detected by mass spectrometry are shown below:

[0076]

[0077] Glucose dimer [Disaccharide+Cl] - :377.09m / z

[0078]

[0079...

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Abstract

The invention discloses a straight-chain oligosaccharide library and a preparation method thereof, which relate to a reaction method of the oligosaccharide library. The method comprises the following steps of: adding triphenylphosphine and halohydrocarbon into a container, dissolving into an organic solvent under the protection of nitrogen gas, and stirring to generate triphenylphosphine dihalide; and adding 1 equivalent of monosaccharides which are dehydrated in vacuum into triphenylphosphine dihalide in a nitrogen gas atmosphere, stirring to generate a mixture, distilling under reduced pressure for removing the organic solvent, adding water, stirring under an ice water bath to generate a mixture, performing a suction filtration under reduced pressure, washing undissolved substances with ice water, and extracting a filtrate with CH2Cl2 to obtain a straight-chain oligosaccharide library. An oligosaccharide library is formed by performing an oligomerization reaction on monosaccharides in an organic solvent in a way of taking triphenylphosphine dihalide as an oligomerization reagent. In the method, monosaccharides such as pentose, hexose and the like serving as raw materials are oligomerized into oligosaccharide libraries containing different quantity of monosaccharides in an organic solvent by taking triphenylphosphine dihalide as an oligomerization reagent, and the connection ways of glucosidic bonds in the oligosaccharide libraries are uniform, so that a straight-chain oligosaccharide library is formed.

Description

technical field [0001] The invention relates to a reaction method of an oligosaccharide library, in particular to a linear oligosaccharide library and a preparation method thereof. Background technique [0002] Since the hydroxyl groups of monosaccharides are numerous and have certain activities, the hydroxyl groups on monosaccharides are usually protected and deprotected during the oligomerization process. In addition, the formation of glycosidic bonds also has a certain regio and stereochemical selectivity. All these factors greatly increase the difficulty of oligosaccharide synthesis, and the commonly used synthesis methods are carried out in solid phase or liquid phase, which can be roughly divided into the following two categories: [0003] 1) React with unprotected glycosyl acceptor and protected glycosyl donor. [0004] 2) Reaction with a protected glycosyl acceptor and a protected glycosyl donor (see: Schweizer F, Hindsgau O. Current Opinion in Chemical Biology, 19...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H3/04C07H3/06C07H1/00C08B37/00B01J31/24
Inventor 赵玉芬袁航刘艳史琛唐果
Owner XIAMEN UNIV
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