Sulfonated Lewis X trisaccharide and synthesis method and application thereof

A synthesis method and a sulfonation technology, which are applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of LeX and its derivatives being lengthy and complex, and no published literature has been found, and achieve high yield and synthesis. The effect of few steps and high reaction selectivity

Inactive Publication Date: 2019-05-17
TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Despite the development of new synthetic methods, the synthesis of LeX and its derivatives is still a lengthy and complicated proce

Method used

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  • Sulfonated Lewis X trisaccharide and synthesis method and application thereof
  • Sulfonated Lewis X trisaccharide and synthesis method and application thereof
  • Sulfonated Lewis X trisaccharide and synthesis method and application thereof

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Embodiment Construction

[0057] The embodiments of the present invention will be described in detail below. It should be noted that the embodiments are illustrative, not restrictive, and cannot limit the protection scope of the present invention.

[0058] The raw materials used in the present invention, unless otherwise specified, are conventional commercially available products; the methods used in the present invention, unless otherwise specified, are conventional methods in the art.

[0059] A kind of sulfonated Lewis X trisaccharide, its general structural formula is as follows:

[0060]

[0061] in:

[0062] R 1 , selected from hydrogen atom, α- or β-configuration serine residue, α- or β-configuration threonine residue, azide substituted alkyl, alkynyl substituted alkyl, mercapto substituted alkyl, α- or β-configuration substituted alkyl;

[0063] R 2 , selected from hydrogen atom, sulfonic acid group, phosphoric acid group, carbonic acid group.

[0064] A kind of synthetic method of sulf...

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Abstract

The invention relates to sulfonated Lewis X trisaccharide having the following structural formula as described in the description, wherein R1 is selected from a hydrogen atom, an alpha- or beta-configuration serine residue, an alpha- or beta-configuration threonine residue, an azide-substituted alkyl group, an alkynyl-substituted alkyl group, a sulfydryl-substituted alkyl group, an alpha- or beta-configuration substituted alkyl group; R2 is selected from the hydrogen atom, a sulfonic acid group, a phosphoric acid group and a carbonic acid group. The method has the advantages of less synthesissteps, high reaction selectivity, high yield and good stereoselectivity. In addition, the 3'-sulfonated modified LeX trisaccharide and the natural ligand -SLeX tetrasaccharide of E-Siglec show similaranti-inflammatory activity by anti-inflammatory activity evaluation. Compared with the Lex trisaccharide, the anti-inflammatory activity has significant difference, that is, the sulfonated Lewis X trisaccharide has good anti-inflammatory activity and can be applied in drug development.

Description

technical field [0001] The invention belongs to the technical field of sugar drugs, and relates to a chemical synthesis method of sugar substances, in particular to a sulfonated Lewis X trisaccharide and its synthesis method and application. Background technique [0002] Lewis X (LeX) is a class of trisaccharide compounds found at the ends of sugar chains, which are often sialylated or sulfonated. A typical example is 6'-sulfated SLeX, which is the terminal oligosaccharide of the high endothelial postcapillary venule (HEV)-associated glycoprotein GLYCAM-1, and 6'-sulfated SLeX in which the primary hydroxyl group of acetylglucosamine residues is monosulfated. Sulfated SLeX and 6,6'-disulfated SLeX, in which the two primary hydroxyl groups of acetylglucosamine residue and galactose residue are both sulfonated, may be the determinants of GLYCAM-1 glycoprotein. These diverse sulfonated oligosaccharides also serve as potential L-selectin ligands and play an important role in the...

Claims

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Application Information

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IPC IPC(8): C07H15/04C07H1/00A61P29/00
Inventor 孟欣袁丁郁彭沈棣李婷申
Owner TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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