CN105085693A - 1,2,3-triazole starch derivatives, and preparation method and application thereof - Google Patents
1,2,3-triazole starch derivatives, and preparation method and application thereof Download PDFInfo
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- CN105085693A CN105085693A CN201510420101.9A CN201510420101A CN105085693A CN 105085693 A CN105085693 A CN 105085693A CN 201510420101 A CN201510420101 A CN 201510420101A CN 105085693 A CN105085693 A CN 105085693A
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Abstract
The invention relates to the field of daily chemicals and medicine industry, specifically to 1,2,3-triazole starch derivatives, and a preparation method and application thereof. The 1,2,3-triazole starch derivatives have a structural formula as shown in a formula (1), wherein R is a chain-length-equivalent substituted group containing different active groups; and a value range of an average polymerization degree n is 5 to 12000. According to the invention, reaction is highly efficient; popularization is easy; and needed equipment and raw materials are easily available. Research results show that the synthesized 1,2,3-triazole starch derivatives have good water solubility and excellent antibacterial activity, strengthen biological activity of starch, expand the application range of the starch, and can be extensively applied in the fields of daily chemicals and medicines.
Description
Technical field
The present invention relates to household chemicals field and pharmaceutical industries, specifically a kind of 1,2,3-triazole class starch derivative and its preparation method and application.
Background technology
Starch (Starch) is polymeric carbohydrate, and chemical structural formula is (C
6h
10o
5) n, be to link together formed covalent polymer through glycosidic link after sloughing water molecules by D-Glucose.Starch is mainly derived from corn, wheat, potatoes and other crops, is the chief component of human foods.In starch molecule, glucose unit has two kinds of mode of connection, forms two kinds of different starch molecules, i.e. amylose starch and amylopectin.Starch is cheap and easy to get, environmental protection, have good biocompatibility and biodegradability, in the industry such as food, pharmacy, papermaking, packaging and weaving, obtain certain application.But native starch molecule, because only have a kind of active group of hydroxyl, lacks carboxyl, sulfate group, amino isoreactivity group and cannot obtain more deeply applying widely.Therefore, by carrying out modifying for chemical structure targetedly to it, introducing active group, expanding its range of application, improve its using value, to the high-valued exploitation of starch, become the new focus of starch research.At present about the relevant utilization of this renewable resources, relative to other polysaccharide having higher producing level, report less.
Known by the mensuration of the bacteriostatic activity to starch, the bacteriostatic activity of starch itself is lower, is not enough to develop, and therefore carrying out appropriate modifying for chemical structure to it is then solve the effective method of this problem.1,2,3-triazole compound is obtained by Huisgen1,3-Dipolar Cycloaddition.Huisgen1,3-Dipolar Cycloaddition is simple to operate, mild condition, product yield are high, reaction is quick, the easy purifying of product, be widely applied to the biomedical sector such as drug development, Macroscopic single crystal, finishing and hydrogel and microgel, nanoparticle, microarray and self-assembly, arrive a lot of compound of good performance.1,2,3-triazole of Isosorbide-5-Nitrae-replacement has larger moment of dipole, and the nitrogen-atoms being positioned at ring 2,3-position can serve as weak hydrogen bond receptor, can strengthen the water-soluble of compound.According to the literature, 1,2,3-triazole group has fabulous bacteriostatic activity, and the group such as carboxyl and halogen also has certain bacteriostatic activity, as by 1,2,3-triazole group and carboxyl or halogen isoreactivity group and starch couple together, to obtaining the starch derivative of high bacteriostatic activity.
Summary of the invention
The object of the invention is to provide a kind of 1,2,3-triazole class starch derivative with better bacteriostatic activity and its preparation method and application.
For achieving the above object, the technical solution adopted in the present invention is:
The advantage that the present invention has:
(1) the compounds of this invention, can directly and end alkyne reaction generation 1,2,3-triazole class starch derivative after introducing azido-compared with starch.
(2) after the present invention is prepared into 1,2,3-triazole class starch derivative, its biological activity is improved, such as: bacteriostatic activity.
(3) on synthesis technique, this synthetic method has following advantage: synthesis step of the present invention is simple, required equipment and raw material is easy to get, cost is lower, be easy to promote, and this product yield is higher, can reach more than 60%.Products obtained therefrom of the present invention can be widely used in the fields such as biology, medicine, food, chemical industry.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of starch.
Fig. 2 provides the infrared spectrum of bromo starch for the embodiment of the present invention, as can be seen from Figure 2 compared with starch material, and 667cm
-1the absorption peak at place is the absorption peak of C-Br key, above analytical data, prove bromo Starch synthesis, simultaneously due to sterically hindered existence, on C-6 position, the reactive behavior of primary hydroxyl is the strongest, namely reaction generates bromo starch at the reaction temperatures, and the hydroxyl of other position is difficult to reaction, therefore namely obtains bromo starch by controlling reaction conditions.
Fig. 3 provides the infrared spectrum of nitrine starch for the embodiment of the present invention, as can be seen from Figure 3 compared with starch material, and the 2105cm newly increased
-1place's absorption peak is the absorption peak of azido group, simultaneously compared with Fig. 2, and 667cm
-1place absorption peak disappear, show azido-nucleophilic substitution bromine obtain nitrine starch.
Fig. 4 provides 6-(4-brooethyl)-1,2, the 3-infrared spectrum of triazole starch for the embodiment of the present invention.As can be seen from Figure 4 compared with Fig. 3 nitrine starch, 2105cm
-1azido group absorption peak disappear, 1531cm
-1triazole ring on the absorption peak of unsaturated link(age), show nitrine starch completely and end alkyne reaction generate 1,2,3-triazole class starch derivative.
Fig. 5 provides 6-(4-chloromethyl)-1,2, the 3-infrared spectrum of triazole starch for the embodiment of the present invention.
Fig. 6 provides 6-(4-carboxyl)-1,2, the 3-infrared spectrum of triazole starch for the embodiment of the present invention.
2105cm in above-mentioned Fig. 5-6
-1the absorption peak of place's azido-disappears, 1550cm
-1left and right produces the infrared absorption peak of triazole ring, have also appeared 1724cm in Fig. 6
-1the infrared absorption peak of carboxylic acid group, therefore can prove the successful synthesis of 1,2,3-triazole class starch derivative.
Embodiment
First this research prepare bromo starch, then utilizes sodium azide nucleophilic substitution bromine to obtain nitrine starch, utilizes click chemistry to react in end alkynes access starch molecule, obtain 1,2,3-triazole class starch derivative, and have studied it to colibacillary restraining effect.This analog derivative prepares easy, mild condition, and the development for carbohydrate fungistat provides feasible thinking.
Embodiment 1
The amyloid synthetic route of 1,2,3-triazole is as follows:
Wherein R be containing different activities group etc. chain length substituting group; The average span of n is 5-12000.
The present embodiment is by above synthetic route synthesising target compound 1,2,3-triazole class starch.
1) preparation of bromo starch: 1.62g starch (see Fig. 1) activates 1h in 50mLDMF (DMF) at 130 DEG C, then cools to 90 DEG C, adds 2.00g lithiumbromide hydrotropy.Under ice bath, add 7.12gN-bromo-succinimide, 10.49g triphenylphosphine, at 80 DEG C of reaction 3h.Then use alcohol settling, through ethanol and washing with acetone, lyophilize, obtains product bromo starch (see Fig. 2) 2.01g, stand-by.
2) preparation of nitrine starch: 0.23g bromo starch (see Fig. 2) is added in 15mLDMSO (methyl-sulphoxide); then 0.16g sodium azide is added; 80 DEG C of reaction 24h under argon shield; then directly use alcohol settling; and with ethanol and washing with acetone; lyophilize obtains nitrine starch (see Fig. 3) 0.16g, stand-by.
3) 6-(4-brooethyl)-1; 2; the preparation of 3-triazole starch: 0.18g nitrine starch (see Fig. 3) is added to 10mLDMF (N; dinethylformamide) in; then the bromo propine of 0.23mL is added; the triethylamine of 0.14mL, the cuprous iodide of 20mg, reacts 72h under argon shield under 75 DEG C of conditions.And then add the bromo propine of 0.23mL, the triethylamine of 0.10mL, the cuprous iodide of 10mg; under 75 DEG C of conditions, 72h is reacted under argon shield; after reaction terminates, with acetone precipitation, suction filtration; washing; deionized water dialysis 36h, vacuum lyophilization, obtains 6-(4-brooethyl)-1; 2,3-triazole starch (see Fig. 4).
Embodiment 2
Difference from Example 1 is:
1) preparation of bromo starch: 1.62g starch (see Fig. 1) activates 1h in 50mLDMF (DMF) at 120 DEG C, then cools to 80 DEG C, adds 2.0g lithiumbromide hydrotropy.Under ice bath, add 5.34gN-bromo-succinimide, 7.87g triphenylphosphine, at 70 DEG C of reaction 3h.Then use alcohol settling, through ethanol and washing with acetone, lyophilize, obtains product bromo starch (see Fig. 2) 1.84g, stand-by.
2) preparation of nitrine starch: 0.23g bromo starch (see Fig. 2) is added in 10mLDMSO (methyl-sulphoxide); then 0.13g sodium azide is added; 70 DEG C of reaction 24h under argon shield; then directly use alcohol settling; and with ethanol and washing with acetone; lyophilize obtains nitrine starch (see Fig. 3) 0.14g, stand-by.
3) 6-(4-chloromethyl)-1; 2; the preparation of 3-triazole starch: 0.19g nitrine starch (see Fig. 3) is added to 10mLDMF (N; dinethylformamide) in; then the chloro propine of 0.22mL is added; the triethylamine of 0.14mL, the cuprous iodide of 20mg, reacts 72h under argon shield under 75 DEG C of conditions.And then add the chloro propine of 0.22mL, the triethylamine of 0.10mL, the cuprous iodide of 10mg; under 75 DEG C of conditions, 72h is reacted under argon shield; after reaction terminates, with acetone precipitation, suction filtration; washing; deionized water dialysis 36h, vacuum lyophilization, obtains 6-(4-chloromethyl)-1; 2,3-triazole starch (see Fig. 5).
Embodiment 3
Difference from Example 1 is:
1) preparation of bromo starch: 1.62g starch (see Fig. 1) activates 1h in 50mLDMF (DMF) at 120 DEG C, then cools to 90 DEG C, adds 2.0g lithiumbromide hydrotropy.Under ice bath, add 7.12gN-bromo-succinimide, 10.49g triphenylphosphine, 60 DEG C of reaction 4h.Then use alcohol settling, through ethanol and washing with acetone, lyophilize, obtains product bromo starch (see Fig. 2) 1.82g, stand-by.
2) preparation of nitrine starch: 0.23g bromo starch (see Fig. 2) is added in 10mLDMSO (methyl-sulphoxide); then 0.2g sodium azide is added; 70 DEG C of reaction 24h under argon shield; then directly use alcohol settling; and with ethanol and washing with acetone; lyophilize obtains nitrine starch (see Fig. 3) 0.17g, stand-by.
3) preparation of 6-(4-carboxyl)-1,2,3-triazole starch: 0.187g nitrine starch (see Fig. 3) is added to 10mLDMF (N; dinethylformamide) in, then add the propynoic acid of 0.19mL, under argon shield, under 75 DEG C of conditions, react 24h; after reaction terminates, with acetone precipitation, suction filtration; washing; deionized water dialysis 48h, vacuum lyophilization, obtains 6-(4-carboxyl)-1; 2,3-triazole starch (see Fig. 6).
Application examples
Suppress the mensuration of intestinal bacteria ability:
Employing reduced turbidity method measures synthesized 1 respectively, 2, the colibacillary ability of suppression of 3-triazole class starch and starch also contrasts: will prepare in embodiment 1,2,3-triazole class starch and experiment are with after starch vacuum lyophilization to constant weight, with water as solvent, after being mixed with the sample aqueous solution of 10mg/mL, get 0.2mL respectively, it is in the substratum of 20mL, 19mL and 18mL that 1mL and 2mL sample solution is added to volume, is mixed with the substratum that sample concentration is 0.1mg/mL, 0.5mg/mL and 1mg/mL.With isocyatic Azythromycin for positive control, with isopyknic sterilized water for negative control, with isocyatic substratum for blank, isopyknic for examination bacterium liquid respectively to accessing in above-mentioned various substratum, 37 DEG C, cultivate 24h under 120r/min condition.The bacterium liquid measuring 8h and 16h in culturing process is respectively the absorbancy at 600nm place at wavelength, and the bacteriostasis rate of calculation sample, repeats once.
Bacteriostasis rate (%)=1-[(A
sample-A
sample 0)/(A
blank-A
blank 0)] × 100
Table 1, the colibacillary ability of suppression (%) of 1,2,3-triazole class starch and starch
Experimental result: 1 synthesized by the present invention, 2, the suppression intestinal bacteria ability of 3-triazole class starch and starch is as shown in table 1, synthesized by the present invention 1, the amyloid bacteriostasis of 2,3-triazole is obviously better than starch, especially 6-(4-carboxyl)-1, the bacteriostasis rate of 2,3-triazole starch when 1mg/mL can reach more than 98%.
Claims (8)
1. a triazole class starch derivative, is characterized in that: 1,2,3-triazole class starch derivative structural formula such as formula shown in (1),
Wherein, R be containing different activities group etc. chain length substituting group; Mean polymerisation degree n span is 5-12000.
2., by 1,2,3-triazole class starch derivative according to claim 1, it is characterized in that: described R is brooethyl, chloromethyl or carboxyl.
3. the preparation method of 1,2, a 3-triazole class starch derivative according to claim 1, is characterized in that:
First starch and N-bromo-succinimide and triphenylphosphine are obtained by reacting bromo starch, gained bromo starch reacts to obtain nitrine starch again with sodium azide, reaction gained nitrine starch and end alkynes class are reacted, namely product is purified obtains such as formula 1 shown in (1), 2,3-triazole class starch derivative;
The molar weight of described N-bromo-succinimide and triphenylphosphine is respectively 3-4 times of starch molar weight; The molar weight of sodium azide is 2-3 times of bromo starch molar weight; The molar weight of end alkynes class is 2-3 times of nitrine starch molar weight.
4. by the preparation method of 1,2,3-triazole class starch derivative according to claim 3, it is characterized in that: described starch dispersion activates 1-2h in excessive DMF at 120-130 DEG C, then cool to 80-90 DEG C, add starch molar weight 2-3 lithiumbromide hydrotropy doubly, under ice bath, add N-bromo-succinimide and triphenylphosphine again, at 70-80 DEG C of reaction 3-4h, then use alcohol settling, more successively through ethanol and washing with acetone, lyophilize, namely obtains bromo starch stand-by.
5. by the preparation method of 1,2,3-triazole class starch derivative according to claim 3, it is characterized in that: described bromo starch and sodium azide react 18-24h at 70-80 DEG C, then directly use alcohol settling, more successively through ethanol and washing with acetone, lyophilize, namely obtains nitrine starch stand-by.
6. by the preparation method of 1,2,3-triazole class starch derivative according to claim 3, it is characterized in that: described nitrine starch and end alkynes are under triethylamine and cuprous iodide catalysis, and at 75-80 DEG C of reaction 12-24h, after reaction, purifying obtains 1,2,3-triazole class starch derivative; Wherein, end alkynes is propine bromine, propine chlorine or propynoic acid.
7. by according to claim 61,2, the preparation method of 3-triazole class starch derivative, it is characterized in that: described reaction after product is through acetone precipitation, throw out is dissolved in distilled water again, and is placed in dialysis tubing and uses distill water dialysis 36-48h, more namely obtains such as formula 1 shown in (1) after lyophilize, 2,3-triazole class starch.
8. the application of 1,2, a 3-triazole class starch derivative according to claim 1, is characterized in that: described 1,2,3-triazole class starch derivative is for the preparation of fungistat.
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| CN105968217B (en) * | 2016-05-05 | 2018-07-31 | 中国科学院烟台海岸带研究所 | A kind of acetylated starch quaternary phosphonium salt and its preparation method and application |
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