2'-OH derivative of alpha-galactose glycosphingolipids and preparing method thereof

A technology for glycosphingolipids and derivatives, which is applied in the field of 2'-OH derivatives of α-galactosphingolipids and their preparation, can solve the problems of different configuration ratios of glycosylation products, difficulties in purification, separation, identification, and limitations. Glycosphingolipid research progress and other issues, to achieve the effect of simple method, short route and easy control of conditions

Inactive Publication Date: 2007-08-08
OCEAN UNIV OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the amount of natural products of such derivatives is too small, and it is difficult to purify, separate, and identify them, which greatly limits the research progress of glycosphingolipids.
Chemical synthesis is an alternative method. The current chemical synthesis method is to first synthesize the glycosylation donor whose 2-hydroxyl group on the galactose ring is modified, and then perform glycosylation reaction with the sphingosine acceptor. The disadvantage of this method is Different substituents of the 2-hydroxyl group on the galactose ring will affect the configuration ratio of the glycosylated product, so the conditions for glycosylation are not universal

Method used

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  • 2'-OH derivative of alpha-galactose glycosphingolipids and preparing method thereof
  • 2'-OH derivative of alpha-galactose glycosphingolipids and preparing method thereof
  • 2'-OH derivative of alpha-galactose glycosphingolipids and preparing method thereof

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Embodiment Construction

[0009] First, glycosidation reaction: 2.4mmol glycosyl donor 3-O-benzyl-4,6-O-benzylidene-2-O-p-methoxybenzyl-p-methylthioglucoside, 2.0mmol containing Add phytosphingosine acceptors with 5-18 carbon atoms and newly activated 4 Å molecular sieves into a mixed solvent of 63mL dichloromethane, diethyl ether, and tetrahydrofuran (the volume ratio of the three is 1:5:1), and cool to -20°C. Under the protection of argon, 3.2 mmol of N-iodosuccinimide (NIS) and 0.2 mmol of catalyst silver trifluoromethanesulfonate (AgOTf) were sequentially added. The reaction solution was stirred for 30 minutes and then placed at 0° C. for glycosylation reaction for 12 hours. Filter off the molecular sieves, the filtrate is concentrated, and the residue obtained after concentration is dissolved in 50mL of dichloromethane, followed by 10% (weight percent concentration, the same below) Na 2 S 2 o 3 aqueous solution, washed with saturated brine, and the dichloromethane organic layer was dried over ...

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Abstract

The invention discloses a making method of 2'-OH derivant of alpha-galactose sphislycolipid, which comprises the following steps: synthesizing intermediate of alpha--galactose sphislycolipid through 3-O-benzyl-4, 6-O-benzal-2-O-p-methoxybenzyl p-methyl bentiamine and plant sphingol under N-iodosuccinimide and catalyst; introducing C18 alkyl, methyl, prenyl or alpha/beta connected galactose radical into naked -OH derivant on the intermediate without 2' p-methoxybenzyl; reducing azido group into amino group; acylating with aliphatic acid acted by accelerator; hydrogenating through palladium agent or liquid amino-metal sodium to reduce.

Description

technical field [0001] The invention relates to a 2'-OH derivative of α-galactosphingolipid and a preparation method thereof. Background technique [0002] In the past ten years, many α-galactosphingolipids (α-GalGSLs) compounds have been isolated from sponges. Studies have shown that α-GalGSLs are a class of molecules that can promote immunity, and can selectively activate NKT cells in vitro to exert their immune regulation and anti-tumor effects. For example, KRN7000, which has entered clinical research, is the simplest α-GalGSL, which can be passed Regulate the immune system to play an anti-tumor effect. The structure of glycosphingolipid molecule is composed of sugar chain, fatty acid and long-chain base of sphingosine. Some of the sugar chains are linked to the primary hydroxyl groups of sphingosine. The structural feature of α-GalGSLs is that the reducing end of the sugar chain is a galactose, and it is connected with ceramide through α-glycosidic bonds. The curren...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/04
Inventor 李英霞丁宁李春霞王鹏
Owner OCEAN UNIV OF CHINA
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