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Synthesis method of oligosaccharide of Lewis x unimer, dimer and saliva acidifying derivatives thereof

A synthetic method and an enzymatic technology, applied in the field of carbohydrate synthesis, can solve the problems of many reaction steps and low overall yield, and achieve the effects of high assembly efficiency, high catalytic efficiency and high protein expression.

Inactive Publication Date: 2018-06-08
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For chemical synthesis, due to the inherent activity of the polyhydroxy structure of the sugar chain itself, repeated protection and deprotection operations are required to ensure regio and stereoselectivity during the synthesis process, resulting in many reaction steps and low overall yield.

Method used

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  • Synthesis method of oligosaccharide of Lewis x unimer, dimer and saliva acidifying derivatives thereof
  • Synthesis method of oligosaccharide of Lewis x unimer, dimer and saliva acidifying derivatives thereof
  • Synthesis method of oligosaccharide of Lewis x unimer, dimer and saliva acidifying derivatives thereof

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Experimental program
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Embodiment approach

[0075] Another embodiment of the present application provides a method for synthesizing the core skeleton sugar chain 2,

[0076] (1) Using enzymatic modular assembly 1 (such as Figure 4 As shown) N-acetylglucosamine is coupled to the tetrasaccharide shown in formula (VII) by β1-3 glycosidic bond, and the pentasaccharide shown in formula (VIII) is synthesized;

[0077] (2) Using enzymatic modular assembly 2 (such as Figure 5 As shown) galactose is coupled to the pentasaccharide shown in formula (VIII) with a β1-4 glycosidic bond, and the hexasaccharide shown in formula (IX) is synthesized;

[0078]

[0079] Wherein, R in formula (VII)~(IX) 1 It is hydroxyl, azide substituted alkyl, alkynyl substituted alkyl, mercapto substituted alkyl, α- or β-configuration substituted alkyl, α- or β-configuration serine residue, α- or β-configuration threo amino acid residues;

[0080] In the enzymatic modular assembly 1, the enzymes that modify N-acetylglucosamine to obtain intermed...

Embodiment 1

[0110] Example 1: Le x and sLe x Synthesis of monomeric and dimer oligosaccharides

[0111] Proceed as follows:

[0112] (1) Chemical synthesis of β-configuration lactosin 1 (Galβ1, 4GlcβProN 3 )

[0113] Add lactose 10 (10 g, 29.23 mmol), acetic anhydride (55 mL) and sodium acetate (9.6 g) into a 500 mL round bottom flask, and stir under reflux at 160°C for 6 hours. Thin layer chromatography (PE:EA=1:1) detected that the reaction was complete, and concentrated by rotary evaporation. The resulting solid was redissolved in 250 mL of dichloromethane, extracted twice with half-saturated saline, three times with saturated sodium bicarbonate solution, and three times with double-distilled aqueous solution, then separated the organic phase, dried the organic phase with anhydrous sodium sulfate, and spun Concentration by evaporation gave compound 11 (18.70 g, 94%) as a pale yellow solid.

[0114] Add compound 11 (1.0 g, 1.47 mmol), dichloromethane (5.0 mL), boron trifluoride di...

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Abstract

The invention discloses a synthesis method of oligosaccharides of a Lewis x unimer, a dimer and saliva acidifying derivatives thereof. The method comprises the steps that core framework compounds (V)to (IX) are built by enzymic method modular assembly 1 and enzymic method modular assembly 2; a Lex unimer and a dimer (I) to (II) are assembled by enzymic method modular assembly 3; finally, an sLexunimer and A dimer (III) to (IV) are built by enzymic method modular assembly 4. High region selectivity and high efficiency of the enzymic method synthesis are combined; the target molecule synthesisis realized at higher yield. Glycosyltransferase, riboside generation enzyme and hexokinase are from prokaryotic organisms; the advantages of high protein expression, wide substrate adaptability, high catalysis efficiency and the like are realized; the synthesis method can be used for large-scale preparation.

Description

technical field [0001] The present invention relates to the synthetic method of carbohydrate substance, relate in particular to a kind of Lewis x (Lewis x x ) Synthetic method of oligosaccharides of monomers, dimers and sialylated derivatives thereof. Background technique [0002] Lewis x[Le x , Galβl-4 (Fucα1-3) GlcNAcβOR] antigen (such as figure 1 shown) and sialylated Lewisx[sLe x , Neu5Acα2-3Galβl-4 (Fucα1-3) GlcNAcβOR] antigen (such as figure 2 shown) is the core structure type II (Galβl-4Glc-NAcβOR) (such as image 3 Shown) Oligosaccharides modified by α1-3 fucosylation and α2-3 sialylation are widely found in human milk oligosaccharides, bacterial lipopolysaccharides, glycolipids and many N- / O-glycans expressed by mammalian cells middle. They play key roles in important biorecognition processes of organisms, such as promoting the growth of beneficial bacteria in the gut microbiota, promoting signaling in cells, cell adhesion, tumor metastasis, preventing pathog...

Claims

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Application Information

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IPC IPC(8): C12P19/18C12P19/04C12P19/00
CPCC12P19/00C12P19/04C12P19/18
Inventor 曹鸿志芦娜陈聪聪刘长城
Owner SHANDONG UNIV
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