CN104974197A - 6-amino-6-deoxidization maltose as well as preparation and application thereof - Google Patents
6-amino-6-deoxidization maltose as well as preparation and application thereof Download PDFInfo
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Abstract
The invention relates to the field of daily use chemical, particularly to 6-amino-6-deoxidization maltose as well as preparation and application thereof. The structure of the 6-amino-6-deoxidization maltose is shown as a formula (1): a 6-hydroxide radical of maltose is bromized, then hydroxide radicals at other sites are protected, and the maltose reacts with sodium azide; after the nitrine reaction, reduction treatment and deprotection are performed, so that the 6-amino-6-deoxidization maltose as shown in the formula (1) is obtained. The 6-amino-6-deoxidization maltose as well as preparation and application thereof, disclosed by the invention, are simple and effective in method, and are easy to generalize. Used raw materials and equipment are simple and easy to obtain. The prepared derivative improves the antioxidative activity of the maltose, greatly enlarges the application range of the maltose and can be widely used in fields of biology, medicines, foods, chemical industry and the like. As shown in the Description.
Description
Technical field
The present invention relates to household chemicals field and pharmaceutical industries, is specifically a kind of 6-amino-6-deoxidation maltose and Synthesis and applications thereof.
Background technology
Maltose is the disaccharide be formed by connecting by α-Isosorbide-5-Nitrae-glycosidic link by two glucose molecules, has reductibility.It is the hydrolysates of macromolecular polysaccharide class material under diastatic katalysis such as starch, glycogen, dextrin, and can make xln, as sweeting agent, sugariness is 1/3rd of sucrose, easily by human consumption and absorption.
Maltose character is gentle, and have good thermostability, heat is low, and it, not only as sweeting agent, is also widely used in food as additive, preservation agent etc.In addition, ultrapure maltose pharmaceutically for intravenous infusion, can be suitably for diabetics and supplements the nutrients, as nutrition agent and the auxiliary therapeutical agent use of diabetic subject.
Aminosugar is the general name of compound that the hydroxyl of carbohydrate is put on record and replaced, and they are at medicine, chemical industry.The aspect tools such as makeup, video, biomedicine have been widely used, mostly as the important component part of biologically active substance or apply as biologically active substance.Containing amino glycan molecule maintain tissue and body structure, keep, in the stability of enchylema, there is vital role, bacterium and poisoning intrusion can be stoped, to organizing the effect playing protection; The synthesis of intracellular biological material can be affected containing aminosugar molecule, and then affect the growth and differ entiation process of cell; Containing aminosugar molecule, also there is the different physiological roles such as anticoagulation, antitumor, strengthening immunity.We are intended to introduce amino on maltose molecule, the physiologically active of maltose can be improved, further provide a kind of compound intermediate more having utility value, improving it can degree of modification, has bioactive compound such as quaternary ammonium salt, Schiff's base etc. lay the foundation for forming other.
Summary of the invention
The object of the invention is to provide a kind of 6-amino-6-deoxidation maltose and Synthesis and applications thereof.
For achieving the above object, the technical solution adopted in the present invention is:
A kind of 6-amino-6-deoxidation maltose, 6-amino-6-deoxidation maltose structure such as formula shown in (1),
A kind of preparation method of 6-amino-6-deoxidation maltose; by the 6-hydroxyl of maltose through bromo, afterwards other hydroxyls are protected, then again with reaction of sodium azide; reduction treatment after azide reaction deprotection, obtain 6-amino-6-deoxidation maltose shown in formula (1).
It is maltose and N-bromo-succinimide (NBS) and triphenylphosphine (PPh that described maltose primary hydroxyl carries out bromo-reaction
3) under 70-80 DEG C of condition, react 4-8h, then purified and freeze-dried back; Wherein, NBS and PPh
3molar weight be respectively the 3-5 of maltose doubly.
It is described that after bromo, carry out protection to other hydroxyls of maltose be gained bromination maltose and diacetyl oxide are reacted 12-24h under 10-25 DEG C of condition, then purified and freeze-dried back; Wherein, the molar weight of diacetyl oxide is 8-10 times of maltose.
Described azide reaction under 60-80 DEG C of condition, reacts 8-16h with sodiumazide after protecting his position hydroxyl of maltose after bromo to obtain 6-nitrine-6-deoxidation maltose; Wherein the molar weight of sodiumazide is 3-5 times of maltose.
Reduction treatment after described azide reaction deprotection be azide reaction product through triphenylphosphine or lithium aluminium hydride reduction, and in hydrazine hydrate or sodium methylate deprotection, then purifiedly namely obtain 6-amino-6-deoxidation maltose shown in formula (1).
Described lithium aluminium hydride reduction is that azide reaction product and lithium aluminum hydride react 24-48h at 20-50 DEG C; Lithium aluminum hydride is 3-5 times of maltose; The reduction of described triphenylphosphine continues after adding 1-5mL pure water after azide reaction product and triphenylphosphine react 24h at 15-25 DEG C in system to react after 24h through purifying and freeze-dried back; The molar weight of triphenylphosphine is 3-5 times of maltose.
In described hydrazine hydrate, deprotection is that reduzate and 85% hydrazine hydrate react 4-8h in 80-100 DEG C; Wherein, the molar weight of hydrazine hydrate is 8-10 times of maltose; In described sodium methylate, deprotection is that reduzate and sodium methylate react 4-8h in 10-25 DEG C; Wherein, the molar weight of sodium methylate is 8-10 times of maltose.
An application for 6-amino-6-deoxidation maltose, described 6-amino-6-deoxidation maltose is for the preparation of antioxidant.
The advantage that the present invention has:
1. the present invention obtains 6-amino-6-deoxidation maltose by effective synthesizing mean, and synthesis condition easily controls, and required equipment and raw material are easy to get, and cost is lower.
2. the present invention introduces ethanoyl in synthesis step, and the intermediate product of formation can directly be washed, simple to operate and improve productive rate.
3. the present invention introduces active group amino by effective synthesizing mean to maltose, improves the application of maltose in daily use chemicals and medicine and other fields.
4. the reaction conditions that the present invention controls makes to only have six hydroxyls to be replaced by amino.Because triphenylphosphine and the reaction of N-bromo-succinimide generate the steric effect of complexing body, make bromo-reaction can only optionally six generations, good reaction selectivity.
Accompanying drawing explanation
The infrared spectrogram of the maltose that Fig. 1 provides for the embodiment of the present invention.
The infrared spectrogram of the bromoacetyl maltose that Fig. 2 provides for the embodiment of the present invention.
The infrared spectrogram of the 6-nitrine-6-deoxidation maltose that Fig. 3 provides for the embodiment of the present invention.
The infrared spectrogram of the acetylated maltose of 6-that Fig. 4 provides for the embodiment of the present invention.
Infrared spectrogram after the acetylated maltose deprotection of 6-that Fig. 5 provides for the embodiment of the present invention.
Embodiment
By way of example the present invention is further described again below, provides implementation detail of the present invention, but be not intended to limit protection scope of the present invention.
The present invention synthesizes amino-6 deoxidation maltose of the 6-obtained by effective means; the primary hydroxyl using bromo to replace maltose obtains six easy leavings groups of maltose; nitrine obtains 6-amino-6-deoxidation maltose after nucleophilic substitution also reduction, utilizes ethanoyl protection to be to be beneficial to purifying products.The inventive method is simply effective, is easy to promote, use raw material and equipment simple and easy to get.Gained derivative improves the anti-oxidant activity of maltose, substantially increases the range of application of maltose, can be widely used in the fields such as biology, medicine, food, chemical industry.
6-amino-6-deoxidation maltose of the present invention is the compound shown in formula (1).
Embodiment
Embodiment 1
(1) 3.42g maltose (see Fig. 1) and 7.6g N-bromo-succinimide are dissolved in 80mLN, in N-N,N-DIMETHYLACETAMIDE, slowly add 10.5g triphenylphosphine, after ice-water bath reaction 20min, system temperature is risen to 80 DEG C, continue reaction 3h, liquid is poured in 200mL acetone, separate out precipitation, filter cake washing with acetone three times after suction filtration, precipitation is dissolved in 80mL pyridine, add 15mL diacetyl oxide, after 25 DEG C of reaction 12h, liquid is poured in 300mL frozen water, precipitation is through distilled water, after washed with diethylether, vacuum lyophilization, (see Fig. 2) for subsequent use.
(2) the product 4.1g of step (1) gained is dissolved in 80mL N; in dinethylformamide; add 1.5g sodiumazide; 70 DEG C of reaction 24h; by in reaction solution impouring 300mL frozen water; the precipitation separated out is after distilled water, washed with diethylether, and vacuum lyophilization obtains nitrine acetylize maltose 3.2g, (see Fig. 3) for subsequent use.
(3) the nitrine acetylize maltose 3.2g obtained is dissolved in 80mL tetrahydrofuran (THF), adds 1g lithium aluminum hydride, after reacting 24h at 0 DEG C, add 2mL15% potassium hydroxide solution cancellation reaction.By in reaction solution impouring 200mL acetone, use acetone, the lyophilize of washing with alcohol final vacuum respectively, stand-by (see Fig. 3).
(4) the product 2g that step (3) obtains is dissolved in the 30mL sodium methylate containing 0.8g sodium, 25 DEG C of reaction 4h.After reaction terminates, underpressure distillation, with ethanol, ether washing precipitation respectively, vacuum freezedrying, obtains 6-amino-6-deoxidation maltose (see Fig. 4).
From above-mentioned Fig. 2, compared with maltose raw material, 1751cm
-1the strong absorption peak at place is the charateristic avsorption band of ethanoyl, and after acetyl group protection, 3300-3500cm
-1the absorption peak of place's hydroxyl obviously reduces.As can be seen from Figure 3, at 2109cm
-1the strong absorption peak that place increases newly is the absorption peak of azido group, proves that azido group has successfully been connected in the structure of maltose.As can be seen from Figure 4, after triphenylphosphine reduction, 2109cm
-1the absorption peak of place's nitrine disappears.By the infrared spectrogram after Fig. 5 deprotection, compared with Fig. 2, the product 1751cm after deprotection
-1the absorption peak at place disappears, simultaneously 3394cm
-1the strong absorption peak of place's hydroxyl occurs proving that hydroxyl is taken off.1635cm
-1and 1596cm
-1the absorption peak appearance that place is amino, 6-amino-6-deoxidation maltose synthesizes successfully.
Embodiment 2
Difference from Example 1 is:
(1) 3.42g maltose and 7.6g N-bromo-succinimide are dissolved in 80mL N, in N-N,N-DIMETHYLACETAMIDE, slowly add 10.5g triphenylphosphine, after ice-water bath reaction 20min, system temperature is risen to 80 DEG C, continue reaction 3h, liquid is poured in 200mL acetone, separate out precipitation, after suction filtration, filter cake washing with acetone three times, is dissolved in 80mL pyridine by precipitation, add 15mL diacetyl oxide, after 25 DEG C of reaction 12h, liquid is poured in 300mL frozen water, precipitates after distilled water, washed with diethylether, vacuum lyophilization, for subsequent use.
(2) the product 4.1g of step (1) gained is dissolved in 80mL N; in dinethylformamide; add 1.5g sodiumazide; 70 DEG C of reaction 24h; by in reaction solution impouring 300mL frozen water; the precipitation separated out is after distilled water, washed with diethylether, and vacuum lyophilization obtains nitrine acetylize maltose 3.2g, for subsequent use.
(3) the product 3.2g of step (2) gained is dissolved in 80mL acetone, adds 3.8g triphenylphosphine, after 25 DEG C of reaction 24h, in system, add 1mL water, continue reaction 24h.After reaction terminates, underpressure distillation, precipitates three times with washed with diethylether, vacuum lyophilization, for subsequent use.
(4) the product 2.2g that step (3) obtains is dissolved in the 30mL sodium methylate containing 0.9g sodium, 25 DEG C of reaction 4h.After reaction terminates, underpressure distillation, with ethanol, ether washing precipitation respectively, vacuum freezedrying, obtains 6-amino-6-deoxidation maltose.
Embodiment 3
Difference from Example 1 is:
(1) 1.7g maltose and 3.6g N-bromo-succinimide are dissolved in 50mL N, in N-N,N-DIMETHYLACETAMIDE, 5.3g triphenylphosphine is added in ice-water bath, after ice-water bath reaction 20min, system temperature is risen to 80 DEG C, continue reaction 3h, liquid is poured in 200mL acetone, separate out precipitation, use washing with acetone three times after suction filtration, precipitation is dissolved in 50mL pyridine, add 8mL diacetyl oxide, after 25 DEG C of reaction 12h, liquid is poured in 200mL frozen water, precipitates after distilled water, washed with diethylether, vacuum lyophilization, for subsequent use.
(2) the product 2.4g of step (1) gained is dissolved in 50mL N; in dinethylformamide; add 0.8g sodiumazide; 80 DEG C of reaction 4h; by in reaction solution impouring 200mL frozen water; by the precipitation of precipitation after distilled water, washed with diethylether, vacuum lyophilization obtains nitrine acetylize maltose 1.5g, for subsequent use.
(3) the nitrine acetylize maltose 1.5g of step (2) gained is dissolved in 50mL acetone, adds 1.8g triphenylphosphine, after reacting 24h at 25 DEG C, add 1mL distilled water, continue reaction 24h.After reaction terminates, underpressure distillation, precipitates three times with washed with diethylether, vacuum lyophilization, for subsequent use.
(4) the product 1.3g that step (3) obtains is dissolved in 60mL ethanol, in system, add 13mL 85% hydrazine hydrate solution, after 80 DEG C of reaction 4h, underpressure distillation, precipitation uses ethanol, washed with diethylether, vacuum lyophilization respectively, obtains 6-amino-6-deoxidation maltose.
Application examples
Antioxidative Activity Determination:
(1) mensuration of scavenging hydroxyl resistance of oxidation:
Measure the scavenging hydroxyl ability of synthesized 6-amino-6-deoxidation maltose and maltose respectively and contrast (table 1): after the 6-amino-6-deoxidation maltose prepared in embodiment and experiment maltose vacuum lyophilization to constant weight, respectively with the solution of water preparation different concns.Get prepared solution 1mL, phosphoric acid buffer 1mL (preparation phosphoric acid buffer: take 41.58g Na respectively
2hPO
412H
2o, 5.2887g NaH
2pO
42H
2o, adds water and is settled to 1000mL), the Stigma Croci 1mL of 0.36mg/mL, 2mmol/L EDTA-Fe 0.5mL mixes in test tube, make sample ultimate density be 0.1,0.2,0.4,0.8,1.6mg/mL, react 0.5h in 37 DEG C of water-baths after, working sample is in the absorbancy at 520nm place.Blank group 1mL distilled water substitutes test sample, and control group 1mL distilled water and 1mL phosphate buffer solution substitute sample and hydrogen peroxide (note: sample all surveys three times, averages).
Scavenging hydroxyl ability (%)=[(A
sample-A
blank)/(A
contrast-A
blank)] × 100
Experimental result: the scavenging hydroxyl ability of the 6-amino-6-deoxidation maltose that the present invention synthesizes and maltose is as shown in table 1, can find out that the ability of the scavenging hydroxyl of the 6-amino-6-deoxidation maltose of gained is obviously better than maltose.
Table 1, the scavenging hydroxyl ability (%) of 6-amino-6-deoxidation maltose and maltose
(2) mensuration of superoxide anion resistance of oxidation is removed:
Measure the removing superoxide anion ability of synthesized 6-amino-6-deoxidation maltose and maltose respectively and contrast (table 2): after the 6-amino-6-deoxidation maltose prepared in embodiment and experiment maltose vacuum lyophilization to constant weight, use Tris-HCl buffered soln (the dense HCl of 1.9382gTris+0.8mL, adds water and be settled to 1000mL) compound concentration to be 0.2 respectively, 0.4,0.8,1.6, the solution of 3.2mg/mL.Get the sample solution of 1.5mL different concns, 1.5mL Tris-HCl buffered soln, 0.5ml NADH (468 μMs), then in reaction solution, add 0.5mL PMS (60 μMs), in test tube after mixing, the ultimate density of sample is 0.1,0.2,0.4,0.8,1.6mg/mL, left at room temperature 5min, 560nm place measures absorbancy, blank group 0.5mL Tris-HCl buffered soln replaces NADH (note: sample all surveys three times, averages).
Remove superoxide radical ability (%)=[(A
blank-A
sample)/A
blank] × 100
Experimental result: the removing superoxide anion ability of the 6-amino-6-deoxidation maltose that the present invention synthesizes and maltose is as shown in table 2, can find out that the ability of the removing superoxide anion of the 6-amino-6-deoxidation maltose of gained is obviously better than maltose.
Claims (9)
1. a 6-amino-6-deoxidation maltose, is characterized in that: 6-amino-6-deoxidation maltose structure such as formula shown in (1),
2. the preparation method of a 6-amino-6-deoxidation maltose according to claim 1; it is characterized in that: by the 6-hydroxyl of maltose through bromo; afterwards other hydroxyls are protected; then again with reaction of sodium azide; reduction treatment after azide reaction deprotection, obtain 6-amino-6-deoxidation maltose shown in formula (1).
3. by the preparation method of 6-amino-6-deoxidation maltose according to claim 2, it is characterized in that: it is maltose and N-bromo-succinimide (NBS) and triphenylphosphine (PPh that described maltose primary hydroxyl carries out bromo-reaction
3) under 70-80 DEG C of condition, react 4-8h, then purified and freeze-dried back; Wherein, NBS and PPh
3molar weight be respectively the 3-5 of maltose doubly.
4. by the preparation method of 6-amino-6-deoxidation maltose according to claim 2, it is characterized in that: described after bromo, carry out protection to other hydroxyls of maltose be gained bromination maltose and diacetyl oxide are reacted 12-24h under 10-25 DEG C of condition, then purified and freeze-dried back; Wherein, the molar weight of diacetyl oxide is 8-10 times of maltose.
5., by the preparation method of 6-amino-6-deoxidation maltose according to claim 2, it is characterized in that: described azide reaction under 60-80 DEG C of condition, reacts 8-16h with sodiumazide after protecting his position hydroxyl of maltose after bromo to obtain 6-nitrine-6-deoxidation maltose; Wherein the molar weight of sodiumazide is 3-5 times of maltose.
6. by the preparation method of 6-amino-6-deoxidation maltose according to claim 2; it is characterized in that: reduction treatment after described azide reaction deprotection is that azide reaction product is through triphenylphosphine or lithium aluminium hydride reduction; and in hydrazine hydrate or sodium methylate deprotection, then purifiedly namely obtain 6-amino-6-deoxidation maltose shown in formula (1).
7., by the preparation method of 6-amino-6-deoxidation maltose according to claim 6, it is characterized in that: described lithium aluminium hydride reduction is that azide reaction product and lithium aluminum hydride react 24-48h at 20-50 DEG C; Lithium aluminum hydride is 3-5 times of maltose;
The reduction of described triphenylphosphine continues after adding 1-5mL pure water after azide reaction product and triphenylphosphine react 24h at 15-25 DEG C in system to react after 24h through purifying and freeze-dried back; The molar weight of triphenylphosphine is 3-5 times of maltose.
8., by the preparation method of 6-amino-6-deoxidation maltose according to claim 6, it is characterized in that: in described hydrazine hydrate, deprotection is that reduzate and 85% hydrazine hydrate react 4-8h in 80-100 DEG C; Wherein, the molar weight of hydrazine hydrate is 8-10 times of maltose;
In described sodium methylate, deprotection is that reduzate and sodium methylate react 4-8h in 10-25 DEG C; Wherein, the molar weight of sodium methylate is 8-10 times of maltose.
9. an application for 6-amino-6-deoxidation maltose according to claim 1, is characterized in that: described 6-amino-6-deoxidation maltose is for the preparation of antioxidant.
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| CN111655737A (en) * | 2017-11-21 | 2020-09-11 | 开普敦大学 | Method for synthesizing polymer containing 6-deoxy-6-amino-beta-D-glucopyranoside and precursor thereof |
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| CN111655737A (en) * | 2017-11-21 | 2020-09-11 | 开普敦大学 | Method for synthesizing polymer containing 6-deoxy-6-amino-beta-D-glucopyranoside and precursor thereof |
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