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Polyalliin and preparation method thereof

A technology of polyalliin and polydeoxyalliin, which is applied in the field of polymers, can solve the problem that the product structure depends on oxidation conditions, and achieve good biocompatibility, high efficiency, and mild oxidation conditions

Pending Publication Date: 2022-06-24
ZHEJIANG APELOA JIAYUAN BIOMEDICAL MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The thioether side groups of polyamino acids can be oxidized to sulfoxides or sulfones (Chin. Chem. Lett. 2020, 31, 1931-1935; Biomacromolecules 2019, 20, 3435-3444; Biomacromolecules 2013, 14, 3610-3614), but The structure of the product is strongly dependent on the oxidation conditions, too strong oxidizing agent will easily further oxidize some side groups of sulfoxide to sulfone
The allyl group is also a functional group that is easily oxidized. The side group of polydeoxyalliin has both an allyl group and a thioether structure. At present, in the scope of amino acids and their polymers, no selective oxidation of thioether to sulfoxide groups has been seen. and retain the allyl group report

Method used

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  • Polyalliin and preparation method thereof
  • Polyalliin and preparation method thereof
  • Polyalliin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (1) 2.8130g (10.0mmol) of deoxyalliin-NPC was added to the reaction flask, dissolved with 7.4mL DMSO, and then the DMSO solution (0.1270mol / L, 0.3303mmol) of 2.6mL neopentylamine was added, and the The molar ratio of amino acid-NPC monomer to neopentylamine was 30:1, sealed and placed in an oil bath at 80 °C for 2 days. After the reaction, the original solution was directly poured into ether for precipitation, centrifugation, and the supernatant was discarded. , the obtained polymer was vacuum-dried for 1 day to obtain neopentylamine-terminated polydeoxyalliin with a yield of 71% and a number-average molecular weight of 3.7kDa.

[0045] (2) 0.0603 g of polydeoxyalliin (end-capped with neopentylamine, number-average molecular weight of 3.7kDa) (containing 0.4195 mmol of repeating units of deoxyalliin), dissolved in 6 mL of hexafluoroisopropanol, and added with 85 μL (30 wt% ) of H 2 O 2 (0.8485mmol), H 2 O 2The molar ratio with the repeating unit of polydeoxyalliin i...

Embodiment 2

[0047] Polydeoxyalliin (n-hexylamine-terminated) was prepared according to step (1) of Example 1, except that neopentylamine was replaced with n-hexylamine.

[0048] Polydeoxyalliin (n-hexylamine end-capped, number-average molecular weight is 4.8kDa) is a raw material, and other oxidation conditions are the same as in Example 1, except that H 2 O 2 The molar ratio with the repeating unit of polydeoxyalliin is 5:1, and the reaction time is 3h. The yield of the obtained product polyaliin was 96%.

Embodiment 3

[0050] Other conditions are the same as in Example 1, the difference is that the number-average molecular weight of polydeoxyalliin is 2.5kDa, and the H 2 O 2 The ratio of the repeating unit to polydeoxyalliin is 8:1, the reaction temperature is 10° C., the reaction time is 3h, and the yield of the obtained product polyaliin is 94%.

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Abstract

The invention discloses polyalliin and a method for synthesizing polyalliin through selective oxidation of polydeoxy alliin. According to the invention, the homopolymer of polyalliin or the block copolymer of polyalliin and polyethylene glycol is synthesized by selectively oxidizing the homopolymer of polydeoxy alliin or the block copolymer of polydeoxy alliin and polyethylene glycol for the first time. The oxidation condition is mild, and the polydeoxyalliin can be selectively oxidized into polyalliin in hexafluoroisopropanol. The invention provides a new path for synthesizing polyalliin, and has a huge application prospect in the field of biological materials.

Description

technical field [0001] The invention belongs to the field of macromolecules, and in particular relates to a polyaliin and a method for synthesizing polyaliin through the polymerization of polydeoxyalliin after polymerization. Background technique [0002] Polyamino acids have secondary structures similar to natural proteins, and are polymers with excellent biocompatibility and degradability, which are widely used in drug delivery, bioimaging, antibacterial and other fields. N-carboxyanhydride (NCA) and N-phenoxycarbonylα-amino acids (NPC) are two important methods for synthesizing polyamino acids. [0003] Deoxyaliin (also known as S-allyl cysteine) and alliin (also known as S-allyl cysteine ​​sulfoxide) are sulfur-containing amino acids unique to garlic, which have anti-tumor, Antibacterial and antivirus, scavenging free radicals and other functions (J.Agr.FoodChem., 2015, 63, 10778-10784). In previous studies, the edible and medicinal value of alliin was focused on small...

Claims

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Application Information

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IPC IPC(8): C08G69/42C08G69/48
CPCC08G69/42C08G69/48Y02P20/55
Inventor 何晓东金国首卢艳枝
Owner ZHEJIANG APELOA JIAYUAN BIOMEDICAL MATERIAL
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