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Temperature response water-soluble nonionic polyamino acid and preparation method thereof

A polyamino acid and non-ionic technology, which is applied in the field of water-soluble non-ionic polyamino acids and their preparation, can solve the problems of difficult biocompatibility and biodegradability, and achieves a simple and feasible synthesis method and a wide range of raw material sources. , the effect of a wide range of application prospects

Inactive Publication Date: 2013-02-20
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional smart responsive polymers have great applications in bioseparation and controlled release of drugs, but their biocompatibility and biodegradability are still a problem.

Method used

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  • Temperature response water-soluble nonionic polyamino acid and preparation method thereof
  • Temperature response water-soluble nonionic polyamino acid and preparation method thereof
  • Temperature response water-soluble nonionic polyamino acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation of polyamino acid shown in embodiment 1, formula (II)

[0031]

[0032] (1) first add 25 milliliters of ethylene glycol monomethyl ethers in the round bottom flask, and add 5 grams of glutamic acid, the mass and number ratio of glutamic acid and triethylene glycol monomethyl ether is 1: 4.8 in this system, Place the suspension in an ice-water bath, wait until it is cooled to 0°C, and slowly add 3 ml of concentrated sulfuric acid (wherein, the mass-number ratio of glutamic acid to concentrated sulfuric acid is 1:1.1); return to 30°C after dropping. °C, react at 30 °C for 8 hours. The clear solution was poured into a mixed solution of triethylamine and isopropanol (1:10 by volume), resulting in a white precipitate. Centrifuged to obtain 3.8 grams of white solid, the productive rate was 54.5%; 1 H NMR (400MHz, D 2 O): δ4.30-4.23(t, 2H), 3.80-3.73(t, 1H), 3.72-3.66(t, 2H), 3.40-3.33(s, 3H), 2.66-2.49(m, 2H), 2.25-2.07(m, 2H); C NMR 13 C NMR (400MHz, ...

Embodiment 2

[0035] The preparation of polyamino acid shown in embodiment 2, formula (III)

[0036]

[0037] (1) First add 30 milliliters of diethylene glycol monomethyl ether in a round bottom flask, and add 5 grams of glutamic acid, the mass and number ratio of glutamic acid and diethylene glycol monomethyl ether in this system is 1: 6 , place the suspension in an ice-water bath, wait until it is cooled to 0°C, and slowly add 3 milliliters of concentrated sulfuric acid (wherein, the mass-number ratio of glutamic acid to concentrated sulfuric acid is 1:1.1), return to 20°C, react at 20°C for 48 hours. The clear solution was poured into a mixed solution of triethylamine and isopropanol (1:10 by volume), resulting in a white precipitate. Centrifuged to obtain 4.2 grams of white solid, the productive rate was 51.5%; 1 H NMR (400MHz, D2O): δ4.31-4.22 (t, 2H), 3.82-3.72 (m, 3H), 3.72-3.64 (m, 2H), 3.63-3.56 (m, 2H), 3.39-3.32 ( s, 3H), 2.66-2.49(m, 2H), 2.25-2.07(m, 2H); C NMR 13 C NMR ...

Embodiment 3

[0042] The preparation of polyamino acid shown in embodiment 3, formula (IV)

[0043]

[0044] (1) First add 40 milliliters of triethylene glycol monomethyl ether in the round bottom flask, and add 5 grams of glutamic acid, the mass fraction ratio of glutamic acid and triethylene glycol monomethyl ether in this system is 1: 8 , place the suspension in an ice-water bath, wait until it is cooled to 0°C, and slowly add 3 milliliters of concentrated sulfuric acid (wherein the mass-number ratio of glutamic acid to concentrated sulfuric acid is 1: 1.1); return to 25°C, react at 25°C for 24 hours. The clear solution was poured into a mixed solution of triethylamine and isopropanol (1:10 by volume), resulting in a white precipitate. Centrifuged to obtain 3.7 grams of white solid, the productive rate was 37.1%; 1 H NMR (400MHz, D2O): δ4.32-4.25(t, 2H), 3.81-3.74(m, 3H), 3.73-3.64(m, 6H), 3.63-3.57(m, 2H), 3.40-3.33( s, 3H), 2.67-2.50(m, 2H), 2.23-2.07(m, 2H); C NMR 13 C NMR (400...

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Abstract

The invention provides water-soluble nonionic polyamino acid and a preparation method thereof. The structural formula of the water-soluble nonionic polyamino acid is shown in the formula (I), wherein x is 1 or 2, m is 1, 2 or 3, and n is a number between 30 to 500. The preparation method of the polyamino acid provided by the invention comprises the following steps: (1) glutamic acid or aspartic acid reacts with methoxy polyethylene glycol in the presence of acid catalyst to obtain an amino acid compound with polyethylene glycol on the side chain; (2) the amino acid compound with polyethylene glycol on the side chain reacts with triphosgene to obtain an N-carboxyl-anhydride compound; and (3) the N-carboxyl-anhydride compound performs polymerization reaction under the action of initiator to obtain the water-soluble nonionic polyamino acid. The preparation method provided by the invention has wide raw material sources, low cost and simple and practical synthesis method; and the water-soluble nonionic polyamino acid provided by the invention has wide application prospect in the fields such as controlled release and biosensors and the like.

Description

technical field [0001] The invention relates to a temperature-responsive water-soluble non-ionic polyamino acid and a preparation method thereof, and belongs to the field of macromolecule biological materials and preparation thereof. Background technique [0002] Polyamino acid is a high molecular biomaterial with good biocompatibility and biodegradability, and has broad application prospects in the field of biomaterials. Ordinary water-soluble polyamino acids (such as polylysine, polyaspartic acid, and polyglutamic acid) are polyelectrolytes, which are water-soluble only in a specific pH range, and because of their charge, they will interact with biological substances in the body. Macromolecules aggregate through interaction, so there are limitations in practical applications. Water-soluble nonionic polyamino acids can overcome these difficulties on the basis of retaining the biological characteristics of polyamino acids. However, all long-chain (more than 25 segments) non...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/40C08G69/08
Inventor 李志波陈重一
Owner INST OF CHEM CHINESE ACAD OF SCI