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New type trisaccharide and penta saccharid oligo saccharide antigen, their synthesis method and application in preparation of medicine for inhibiting exclusion reaction

A reaction and compound technology, applied in the field of novel trisaccharide and pentasaccharide oligosaccharide antigens, can solve the problems of low total yield, many synthesis steps, unsatisfactory and other problems

Active Publication Date: 2008-01-30
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are reports in the literature that its synthesis has been studied by chemical and enzymatic methods (see Zhu, T.; Boons, G.-J.J.Chem.Soc., Perkin Trans.1 1998,857; Gege, C.; Kinzy, W .; Schmidt, R.R. Carbohydr. Res. 2000, 328, 459; and Fang, J.; Li, J.; Chen, X.; Zhang, Y.; Wang, J.; .; Yu, L.; Brew, K.; Wang, P.G.J.Am.Chem.Soc.1998, 120, 6635.), but there are many synthetic steps and the total yield is low, which cannot meet the needs of a large number of oligosaccharide samples. Require

Method used

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  • New type trisaccharide and penta saccharid oligo saccharide antigen, their synthesis method and application in preparation of medicine for inhibiting exclusion reaction
  • New type trisaccharide and penta saccharid oligo saccharide antigen, their synthesis method and application in preparation of medicine for inhibiting exclusion reaction
  • New type trisaccharide and penta saccharid oligo saccharide antigen, their synthesis method and application in preparation of medicine for inhibiting exclusion reaction

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Experimental program
Comparison scheme
Effect test

Embodiment 2、 3

[0085] The synthetic steps of embodiment 2, trisaccharide 2:

[0086] (1) Synthesis of Compound 12

[0087] Add 4 Ȧ MS (400 mg), compound 11 (see Koeller, K.M.; Wong, C.-H. Chem. Rev. 2000, 100, 4465.) (100 mg, 0.18 mmol) and compound HO (CH) in a 50 ml reaction vial. 2 ) 3 NHCbz (48.6mg, 0.22mmol), under nitrogen protection, injected into dry CH 2 Cl 2 (10ml) was stirred for 0.5h, NIS (39.5mg, 0.18mmol), TfOH (69μl, 0.5M ether solution, 0.034mmol) were added under ice-water conditions, the reaction was completed after 2h, and triethylamine (1ml) was added to neutralize, Join CH 2 Cl 2 (15ml) was diluted, celite was filtered to remove 4 ȦMS, and the filtrate was successively washed with saturated NaHCO 3 and NaCl, dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was separated by column chromatography [eluent petroleum ether: ethyl acetate (V / V)=1:1] to obtain 56 mg of a light yellow solid, yield 49 %. 1 HNMR (500MHz, DMSO-d 6 )δ: 7.717.92(m...

Embodiment 3、 5

[0094] The synthetic steps of embodiment 3, pentasaccharide 3:

[0095] (1) Synthesis of Compound 14

[0096] Add 4 Ȧ MS (200mg), compound 9 (44.6mg, 0.069mmol), BSP (12mg, 0.063mmol) in 25ml eggplant-shaped bottle, inject dry dichloromethane (2ml), N 2 Protected, stirred for 0.5h, cooled to minus 70°C, injected with Tf 2 O (11.9μl, 19.46mg, 0.069mmol), after reacting for 10min, dissolve compound 10 (30mg, 0.063mmol) with 2ml of dry dichloromethane and add it to the reaction bottle, then slowly rise to room temperature, after 2h, TLC detection shows that the raw material After the reaction, add 2ml of triethylamine and CH 2 Cl 2 (10ml), dilute with diatomaceous earth to remove 4 ȦMS, and the filtrate is successively washed with saturated NaHCO 3 Wash with NaCl, dry over anhydrous sodium sulfate, filter, concentrate, and the residue is separated by column chromatography [eluent petroleum ether: ethyl acetate (V / V)=3:1] to obtain 56 mg of light yellow oil, the yield 90%. 1...

Embodiment 4

[0112] The preparation of embodiment 4 composition

[0113] Prepare 20 mg of the compound of general formula I, II or III of the present invention and 2 ml of physiological saline for injection into injections according to conventional injection preparation methods.

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Abstract

The trisaccharide and pentasaccharide oligose antigens with their disclosed formulas, their preparing process by 'synthesizing in a single reactor', and their application in preparing the medicine for supperssing the rejection reaction of organ transplantation are disclosed.

Description

field of invention [0001] The present invention relates to novel trisaccharide and pentasaccharide oligosaccharide antigens, their "one-pot synthesis" synthesis method, and their use in the preparation of drugs for inhibiting rejection of xenogeneic organ transplantation. Background technique [0002] Xenotransplantation is considered as one of the methods to solve the shortage of donor organs in organ transplantation. Hyperimmune rejection is considered the most challenging obstacle in xenotransplantation. It is caused by a natural antibody called anti-Gal in the human circulatory system that specifically recognizes an antigen containing Gal 1→3Gal-R oligosaccharide fragments expressed on non-primate organ cells. Neutralizing anti-Gal antibody with synthetic oligosaccharide antigen is one of the possible ways to suppress hyperimmune rejection. We successfully constructed a series of oligosaccharide antigens related to xenotransplantation by "one-pot synthesis". [0003] ...

Claims

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Application Information

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IPC IPC(8): C07H3/06A61K31/702A61P37/06
Inventor 叶新山黄雪飞晏青燕张礼和
Owner PEKING UNIV
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