Sulfur-containing polyethylene glycol modified resin

A polyethylene glycol and resin technology, which is applied in the field of sulfur-containing polyethylene glycol modified resins, can solve the problems of substandard performance of modified polyethylene glycol resins and difficult preparation.

Inactive Publication Date: 2020-10-02
苏州金顶生物有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Aiming at the problem that the performance of the above-mentioned modified polyethylene glycol resin is not up to standard or the preparation is difficult, the present invention provides a sulfur-containing polyethylene glycol modified resin and a preparation method. The sulfur-containing polyethylene glycol modified resin provided by the present invention greatly reduces the The synthesis cost of macromolecules such as peptides and nucleic acids has been greatly improved, and the production efficiency has been greatly improved, which has broad application prospects

Method used

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  • Sulfur-containing polyethylene glycol modified resin
  • Sulfur-containing polyethylene glycol modified resin
  • Sulfur-containing polyethylene glycol modified resin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1H2

[0173] Example 1H 2 N-PEG (8~12) -CH 2 CH 2 CH 2 -S-CH 2 CH 2 -COOH (compound 7, R 3 =H)

[0174] 1) HO-PEG (8~12) -CH 2 CH 2 CH2 -S-CH 2 CH 2 -COOtBu synthesis

[0175] Dissolve 1200g (about 2.4mol) of APEG500 in 7L of 1,4-dioxane, under nitrogen protection, add 889g (6mol) of tert-butyl 2-mercaptoacetate, raise the temperature to 55°C, add 93.5g of (0.3 mol) AIBN, when the temperature stabilized to 55°C, the nitrogen protection was removed, and the reaction was carried out at 55°C for 13h, and the reaction was complete by MS detection.

[0176] About 4L of 1,4-dioxane was removed by rotary evaporation under reduced pressure, 10L of water was added, and petroleum ether (5L×3) was used to extract a large amount of unreacted tert-butyl 2-mercaptoacetate. The aqueous layer was adjusted to pH=4 with 40% phosphoric acid (a small amount of acid is enough), extracted with dichloromethane (5L*2), washed once with water, dried with anhydrous sodium sulfate, and evaporate...

Embodiment 2

[0186] Example 2Me-HN-PEG (8~12) -CH 2 CH 2 CH 2 -S-CH 2 CH 2 COOH (compound 9, R 3 = Hydrogen, R 5 = methyl)

[0187] 1) Me-NH-PEG (8~12) -CH 2 CH 2 CH 2 -S-CH 2 CH 2 -COOtBu

[0188] 70g (0.1mol) Tos-O-PEG (8~12) -CH 2 CH 2 CH 2 -S-CH 2 CH 2 -COOtBu was dissolved in 400ml of tetrahydrofuran, cooled to -60°C, and 100ml of 3M methylamine tetrahydrofuran solution was added dropwise. After the addition was complete, it was kept at -60°C and stirred for 3 hours. The solvent was evaporated to dryness under reduced pressure to obtain a pale yellow oil, 400ml of water was added to dissolve the oil, the aqueous phase was extracted with ethyl acetate (200ml×3), the acetic acid was washed once with 200ml of saturated brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. On drying, 53 g of a yellow oil were obtained.

[0189] 2) Me-NH-PEG (8~12) -CH 2 CH 2 CH 2 -S-CH 2 CH 2 -COOH

[0190] 35g (52mmol) NH 2 -PEG (20~30) -CH 2 CH...

Embodiment 3

[0193] NH2-CH2-CH2-S-CH2CH2CH2-PEG(30~40)-CH2CH2COOH (Compound 16, R1=H, R2=H)

[0194] 1) Synthesis of Boc-NH-CH2-CH2-S-CH2CH2CH2-PEG(30~40)-OH (compound 14)

[0195] Dissolve 150g (about 0.1mol) of APEG1500 in 600ml of 1,4 dioxane, under nitrogen protection, add 106g (0.6mol) of Boc-cysteamine (compound 13), heat up to 55°C, add 3.3g of ( 0.02mol) AIBN, when the temperature stabilized to 55°C, remove the nitrogen protection, react at 55°C for 9h, and MS detected that the reaction was complete.

[0196] Remove about 400ml of 1,4-dioxane by rotary evaporation under reduced pressure, add 400ml of water, and extract a large amount of unreacted Boc-cysteamine with petroleum ether (400ml×3). The aqueous layer was adjusted to pH=4 with 40% phosphoric acid, extracted with dichloromethane (300ml×2), washed once with water, dried with anhydrous sodium sulfate, and evaporated to dryness under reduced pressure to obtain Boc-NH-CH 2 -CH 2 -S-CH 2 CH 2 CH 2 -PEG (30~40) -OH103g.

...

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Abstract

Polyethylene glycol monoallyl ether reacts with a sulfhydryl compound containing an amino group or a carboxyl group to obtain sulfur-containing polyethylene glycol, and the structural general formulais shown in the description. The amino group or the carboxyl group is introduced into polyethylene glycol, so that the modified polyethylene glycol is very conveniently introduced into the resin, andthe polyethylene glycol resin with different effects is obtained.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a sulfur-containing polyethylene glycol modified resin. Background technique [0002] Merrifield et al reported the concept of solid-phase peptide synthesis as early as the 1960s, cross-linking styrene into different types of chloromethylated polystyrene [Wu M, Yang G, Chen Z. Polymer supported peroxodisulfate: A mild and clean Oxidation of organic compounds under nonaqueous and aprotic conditions. React Funct Polym, 2000, 44: 97—100; HariA, Miller BL. Exploiting differences in solution vs solid-supported reactivity for the synthesis of sulfonic acid derivatives. 1192910, 9: Org Lett, -2111] as the carrier resin (Merrifield resin, shown below) for solid-phase synthesis of polypeptides. Since then, polymeric solid supports have become more and more common in the synthesis and purification of products. [0003] [0004] Structure of Merrifield Resin and Polyethylene Glycol (PE...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/02C08G65/338C08G65/335C08G65/334C08G65/333C08G65/325C08G65/324
CPCC07K1/042C08G65/325C08G65/3322C08G65/3344C08G65/335C08G65/337C08G65/338Y02P20/55
Inventor 向双春高峰李云平
Owner 苏州金顶生物有限公司
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