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Cysteine-containing saccharide derivative and preparation method thereof

A technology of cystine sugars and derivatives, applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of difficult application, lack of biocompatibility of synthetic polymers, etc., and achieve stable synthesis methods. , the effect of enriching functionality and expanding the scope of applications

Pending Publication Date: 2022-07-29
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although great progress has been made in synthesis in recent years, the preparation of well-defined, highly ordered sugar-containing polymers remains a challenging task, and some synthetic polymers lack biocompatibility, making It is difficult to apply to medical fields such as targeted drug delivery and tissue engineering
Great progress has been made in the synthesis of glycopolymers, but the preparation of well-defined, highly ordered amino acid-containing saccharide derivatives remains a challenging task

Method used

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  • Cysteine-containing saccharide derivative and preparation method thereof
  • Cysteine-containing saccharide derivative and preparation method thereof
  • Cysteine-containing saccharide derivative and preparation method thereof

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preparation example Construction

[0047] The present invention provides a preparation method of cysteine-containing carbohydrate derivatives, comprising the following steps:

[0048] (1) 2-amino-2-methyl-1,3-propanediol reacts with dicarbonyl di-tert-butyl and sodium bicarbonate, and after-treatment obtains the first compound;

[0049] (2) the first compound that step (1) obtains generates Williamson ether synthesis reaction with propargyl bromide and potassium hydroxide, and aftertreatment obtains the second compound;

[0050] (3) the second compound obtained in step (2) is esterified with triethylamine and acryloyl chloride, and the aftertreatment obtains the third compound;

[0051] (4) Thiol-ene click chemical reaction occurs between the third compound obtained in step (3) and N-acetyl-L-cysteine ​​methyl ester and dimethylphenylphosphine, and the fourth compound is obtained after post-processing;

[0052] (5) The fourth compound obtained in step (4) undergoes a CuAAC click chemistry reaction with acetyl-...

Embodiment 1

[0071] This embodiment provides a preparation method of cysteine-containing carbohydrate derivatives.

[0072] (1) Preparation of the first compound

[0073] Take 2-amino-2-methyl-1,3-propanediol (10g, 95.11mmol) and add it to a 500mL dry reaction flask, add 100mL methanol and 25mL tetrahydrofuran mixed solution to dissolve, then dropwise add dicarbonyl di-tert-butyl ( 21.87 mL, 95.11 mmol), stirred in an ice bath for 30 min, added sodium bicarbonate (7.99 g, 95.11 mmol), and reacted at 0°C for 24 h. After the reaction, the solvent was removed by rotary evaporation, ethyl acetate was dissolved, added dropwise to petroleum ether for recrystallization, and 19.0 g of white solid was obtained by filtration, and the yield was 90%.

[0074] For the H NMR spectrum and C NMR spectrum of the first compound, please refer to figure 1 and figure 2 shown.

[0075] The chemical structural formula of the first compound is shown below:

[0076]

[0077] The NMR data for the first com...

Embodiment 2

[0108] This embodiment provides a preparation method of cysteine-containing carbohydrate derivatives.

[0109] (1) Preparation of the first compound

[0110] Take 2-amino-2-methyl-1,3-propanediol (10g, 95.11mmol) and add it to a 500mL dry reaction flask, add 100mL methanol and 25mL tetrahydrofuran mixed solution to dissolve, then dropwise add dicarbonyl di-tert-butyl ( 27.26 mL, 118.88 mmol), stirred in an ice bath for 30 min, added sodium bicarbonate 8.79 g, 104.62 mmol), and reacted at 15°C for 16 h. After the reaction, the solvent was removed by rotary evaporation, dissolved in ethyl acetate, added dropwise to petroleum ether for recrystallization, and filtered to obtain 19.5 g of white solid with a yield of 92%.

[0111] (2) Preparation of the second compound

[0112] The first compound (10.00 g, 58.70 mmol) was dissolved in 150 mL of anhydrous DMF, and placed in an ice-water bath to stir and dissolve, and propargyl bromide (6.89 mL, 88.05 mmol) was added slowly dropwise...

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Abstract

The invention relates to the technical field of synthesis of amino acid-containing saccharide derivatives, in particular to a cysteine-containing saccharide derivative and a preparation method thereof. The preparation method comprises the following steps: firstly, preparing a compound with terminal alkyne and terminal olefin, carrying out Thiol-ene reaction on the terminal olefin and N-acetylcysteine methyl ester, and carrying out CuAAC reaction on the terminal alkyne and acetyl-protected alpha-D-mannopyranose azide to prepare the cysteine-containing saccharide derivative. Compared with the prior art, cysteine and alpha-D-mannopyranosyl azide are successfully combined through a click chemical reaction for the first time, and the amino acid-containing saccharide monomer which can be used for RAFT polymerization and post-polymerization modification is prepared. And a considerable way is provided for obtaining the homopolymer with controllable molecular weight and narrower distribution in the later stage.

Description

technical field [0001] The present invention relates to the technical field of synthesis of amino acid-containing carbohydrate derivatives, in particular to a cysteine-containing carbohydrate derivative and a preparation method thereof. Background technique [0002] Glycopolymers are promising materials with great potential for key biomedical and biotechnological applications such as tissue engineering, drug delivery, or polymer therapy. It has received extensive attention due to its close relationship with native glycoproteins, which play a variety of roles in the human body, ranging from cell recognition, adhesion, and lubrication to cancer cell metastasis and pathogen infection. On the other hand, polyamino acids (components of proteins and peptides) are widely used in medicine, biotechnology and materials science due to their structural diversity, unique self-assembled structures and good biocompatibility. [0003] The main types of click reactions are: (1) Cu(I)-cataly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H19/056
CPCC07H1/00C07H19/056
Inventor 刘美娜周志叶飞刘彩容周欣怡丁欣
Owner SHANGHAI INST OF TECH
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