Synthesis method of human ABH blood group antigen

A synthesis method and blood group antigen technology, which are applied in the field of ABH blood group antigen synthesis, can solve the problems of complex chemical protection, strict operating conditions, low final yield and the like, and achieve excellent catalytic effect, few by-products and high synthesis efficiency. Effect

Inactive Publication Date: 2018-07-06
SHANDONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The chemical method requires complex protection and deprotection processes, and the operating conditions are strict, so that the final yield is low; the source and substrate specificity of the enzyme in the enzymatic synthesis limit the wide use of the enzymatic method, and the whole cell fermentation can only Produces an oligosaccharide structure and is difficult to purify

Method used

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  • Synthesis method of human ABH blood group antigen
  • Synthesis method of human ABH blood group antigen
  • Synthesis method of human ABH blood group antigen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0038] Example: Synthesis of ABH Antigen

[0039] The steps are as follows:

[0040] (1) Chemical synthesis of β-configuration lactose compound 1 (Galβ1, 4GlcβProN3)

[0041] Lactose (10 g, 29.23 mmol), acetic anhydride (55 mL) and sodium acetate (9.6 g) were added to a 500 mL round bottom flask, and stirred under reflux at 160° C. for 6 hours. Thin layer chromatography (PE: EA = 1: 1) after the reaction was complete, concentrated by rotary evaporation. The resulting solid was redissolved in 300 mL of dichloromethane, extracted once with half-saturated saline, extracted three times with saturated sodium bicarbonate solution, extracted three times with double-distilled aqueous solution, then separated the organic phase, dried the organic phase with anhydrous sodium sulfate, and rotary evaporated Concentration afforded Compound 5 (18.6 g, 94%) as a light yellow solid.

[0042] Add compound 5 (1.0 g, 1.47 mmol), dichloromethane (5.0 mL), boron trifluoride diethyl ether (0.36 m...

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Abstract

The invention relates to a synthesis method of saccharides, in particular to synthesis of ABH blood group antigen. The synthesis method comprises the following steps: through a one-pot and multi-enzyme system, coupling fucose to disaccharide shown as a formula (I) by using an alpha1-2 glucosidic bond to synthesize trisaccharide shown as a formula (II); through the one-pot and multi-enzyme system,coupling galactose to the trisaccharide shown as the formula (II) by using an alpha1-3 glycosidic bond to synthesize tetrasaccharide shown as a formula (III); through the one-pot and multi-enzyme system, coupling N-acetylgalactosamine to the trisaccharide shown as the formula (II) by using the alpha1-3 glycosidic bond to synthesize tetrasaccharide shown as a formula (IV). Through utilization of enzymatic modular assembly and full utilization of the high efficiency of various enzymes and the specificity of a substrate, the synthesis of the ABH blood group antigen is completed.

Description

technical field [0001] The invention relates to a method for synthesizing carbohydrates, in particular to the synthesis of ABH blood group antigens. Background technique [0002] ABH blood group antigen is the main blood group antigen of human beings, and the determinants of its epitope are composed of oligosaccharide chains, which can be combined with polypeptides or lipids to form glycoproteins or glycosphingolipids. ABH blood group antigens not only exist on the surface of red blood cells, but also widely exist in epithelial and endothelial cells of human organs, breast milk, saliva and urine, etc. These oligosaccharide antigens are related to acute hemolytic transfusion reactions and immune responses to bone marrow and organ transplantation. More and more studies have shown that these antigens play important roles as receptors in various bacterial, viral and parasitic infections as well as tumor metastasis. [0003] The ABH blood group antigen includes three epitope det...

Claims

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Application Information

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IPC IPC(8): C12P19/18
CPCC12P19/18
Inventor 曹鸿志李芸叶金凤刘长城
Owner SHANDONG UNIV
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