Thomsen-Friedenreich (TF) antigen and TF antigen analogue and their chemoenzymatic synthesis method and use

A synthesis method and analog technology are applied in the field of chemical enzymatic synthesis of tumor-related carbohydrate antigens and their analogs, and can solve the problems of reducing sugar ring electron density and the like

Inactive Publication Date: 2012-11-28
SHANDONG UNIV
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Problems solved by technology

Due to its unique structure, the nine-carbon sugar sialic acid is not only easy to form intramolecular hydrogen bonds, but also the carboxyl group at the C1 position, the deoxygenation at the C3 position, and the nitrogen heteroatom substitution

Method used

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  • Thomsen-Friedenreich (TF) antigen and TF antigen analogue and their chemoenzymatic synthesis method and use
  • Thomsen-Friedenreich (TF) antigen and TF antigen analogue and their chemoenzymatic synthesis method and use
  • Thomsen-Friedenreich (TF) antigen and TF antigen analogue and their chemoenzymatic synthesis method and use

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Experimental program
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Embodiment Construction

[0070] 1. Chemoenzymatic synthesis of T antigen, sT antigen and their fluorinated derivatives

[0071] Synthesis of the compound 2-acetylamino-2-deoxy-D-galactose

[0072] The reaction equation is as follows:

[0073]

[0074] Into a 500mL round bottom flask, add galactosylamino hydrochloride (7.01g, 32.51mmol), acetic anhydride (60mL), pyridine (Pyr 120mL), dimethylaminopyridine (DMAP 1.06g, 8.68mmol), and stir at room temperature for 12h . Thin-layer chromatography detection (petroleum ether: ethyl acetate = 3:2), after the reaction is complete, add 20mL toluene to the reaction solution, rotary evaporation and concentration, repeat 3 times. The obtained solid was redissolved in 30 mL of methanol, placed in ultrasonic for 0.25 h, and then left to stand at 4°C for 12 h. Filtrate, discard the filtrate, collect the resulting solid, and dry to obtain white solid compound 18 (10.75 g, yield 85%).

[0075] Into a 500 mL round bottom flask, add solid compound 18 (5.69 g, 14.8...

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Abstract

The invention discloses a Thomsen-Friedenreich (TF) antigen and a TF antigen analogue and their chemoenzymatic synthesis method and use. The chemoenzymatic synthesis method comprises the following steps of 1, carrying out chemosynthesis of fluorogalactose and a fluoro-galactosamine analogue, 2, carrying out enzymatic synthesis of a fluoro-TF antigen, and 3, carrying out enzymatic synthesis of a sialyl TF antigen. The preparation method has flexibility of a chemosynthesis method, and high regioselectivity and high efficiency of an enzymatic synthesis method, creatively realizes enzymatic synthesis of the fluoro-TF antigen, and solves the problem that the existing fluoro-TF antigen chemosynthesis method has low substrate reactivity, complex synthesis steps and a low yield. A tumor-associated fluoro-carbohydrate antigen is superior to a natural carbohydrate antigen in pharmacokinetic properties and thus the preparation method has wide application prospects in development of a novel anti-tumor vaccine.

Description

technical field [0001] The invention belongs to the field of carbohydrate drugs, and relates to a chemical enzymatic synthesis method of carbohydrate substances, in particular to a chemical enzymatic synthesis method of tumor-associated carbohydrate antigens and their analogs, and also relates to the synthesis of TF antigens, sT antigens and their analogs in pharmaceuticals. Applications in R&D. Background technique [0002] Current studies have shown that there is a common phenomenon in the generation and development of different tumor tissues, that is, abnormal sugar chain structures are overexpressed on the surface of tumor cells, and these sugar chain structures are called tumor-associated carbohydrate antigens (TACAs). The same tumor tissue will express different tumor-associated carbohydrate antigens, and the same tumor-associated carbohydrate antigen will also be distributed in different tumor tissues. These tumor-associated carbohydrate antigens are closely related ...

Claims

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Application Information

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IPC IPC(8): C07H5/06C07H15/04C12P19/26C12P19/44A61K39/385A61P35/00
Inventor 曹鸿志王凤山闫俊
Owner SHANDONG UNIV
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