CN1680571A - Preparation of maltotriose - Google Patents
Preparation of maltotriose Download PDFInfo
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- CN1680571A CN1680571A CN 200510013106 CN200510013106A CN1680571A CN 1680571 A CN1680571 A CN 1680571A CN 200510013106 CN200510013106 CN 200510013106 CN 200510013106 A CN200510013106 A CN 200510013106A CN 1680571 A CN1680571 A CN 1680571A
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- acid
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- trisaccharide maltose
- polysaccharide
- maltotriose
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Abstract
A process of preparing maltotriose. First, Prullan polyoses fermented from spore mold reacts with mixture solution of acid and acetic anhydride and acetyl anhydride. Acetylcholine maltotriose is obtained between -10deg.C and 50deg.C. Second, hydrolyse ethanoyl group at pH 9-10. Finally, purified maltotriose is reached by way of normal reverse-phase chromatography.
Description
Technical field
The present invention relates to a kind of preparation method of trisaccharide maltose.
Background technology
Trisaccharide maltose be three glucose with the oligosaccharides that α-(1 → 4) is connected to form, maltin can starch or raw grain (as crack rice etc.) be raw material, the mixture of trisaccharide maltose to eight sugar that forms through intact hydrolysis.Usually trisaccharide maltose all is that mode by fermentation obtains, but it is still very difficult to prepare the trisaccharide maltose of SILVER REAGENT purity by fermentation method.
Trisaccharide maltose can generate the isomaltose contain α-(1 → 6) key, panose and other is with branched oligose by transglycosylation, to removing stool, suppress the enteron aisle putrefactive bacterium, regulating intestinal health and can play huge effect.
Concerning the diagnosing acute pancreatic disease, measure pancreatic amylase activity in the human serum and be the most practical and sensitive method.Between ten several years in the past, scientific workers invented hundreds of detection method (Clinical Chemistry, 1982,28,2201-2205), its core all is the research and development to sensitive substrate, these substrates by sugar and chromophore form.But most of analytical procedures all need the complexity of sugar moieties to modify, the influence that substrate hydrolysis is caused with the auxiliary enzymes of offsetting in this method of masurement (alpha-glucosidase).Up-to-date achievement in research shows: the substrate of being made up of trisaccharide maltose and 2-chloro-4-nitrophenol is best suited for quick diagnosis (Clinica Chimica Acta, 1998,272, the 137-147 of acute pancreatic disease; ClinicalChemistry, 2000,46,928-933).Therefore, the preparation of simple and easy trisaccharide maltose is significant in the production of this diagnostic reagent.
Summary of the invention
For solving the problem in the above-mentioned technology, the objective of the invention is to propose a kind of preparation method who prepares the trisaccharide maltose of target molecule with synthetic method.
For achieving the above object, technical scheme disclosed by the invention provides a kind of preparation method of trisaccharide maltose, and its method may further comprise the steps:
1) the exocellular polysaccharide pulullan polysaccharide (Pullulan) that is produced by the mould fermentation of the falx that sprouts is a raw material, utilize α in the pulullan polysaccharide-(1 → 6)-glucoside bond to be easy to fracture than α-(1 → 4)-glucoside bond, make it in acid and acetic anhydride mixed solution acetolysls to take place, its ratio is: 1: 100-1: 10; Temperature of reaction is-10 ℃-+50 ℃ and obtains full acetylated trisaccharide maltose;
2) fall ethanoyl with the base strength hydrolysis of pH=9-10;
3) make the pure product of trisaccharide maltose through common reversed phase column chromatography process.
Described acetolysls contains glacial acetic acid, and it is 10-50% that content can reach volume ratio.
Described acid is a kind of of the vitriol oil, Zinc Chloride Anhydrous, trifluoroacetic acid.
Described acid is the mixture of a kind of and glacial acetic acid of the vitriol oil, Zinc Chloride Anhydrous, trifluoroacetic acid.
It is ammonia is saturated under the room temperature methanol solution or sodium methylate-methanol solution of pH value 9-10 that the ethanoyl condition is fallen in described hydrolysis.
Effect of the present invention is the trisaccharide maltose that can be prepared pharmaceutical grade by pulullan polysaccharide in a large number, simplifies the preparation of trisaccharide maltose, for the production of acute pancreatic disease fast diagnosis reagent and to have an exploitation of saccharide compound of prospect in medicine all significant.
Embodiment
Preparation method to trisaccharide maltose of the present invention is illustrated in conjunction with the embodiments.
Its core of the preparation method of trisaccharide maltose of the present invention be by pulullan polysaccharide through acetolysls, thereby obtain full acetylated trisaccharide maltose; Full acetylated trisaccharide maltose makes the pure product of trisaccharide maltose through taking off acetyl.
Pulullan polysaccharide (Pullulan) Chinese also is translated into pullulan, pullulan, general poly-polysaccharide or pulullan.It is the exocellular polysaccharide of the mould generation of falx of sprouting, constitute the homotype polysaccharide based on α-(1 → 6) glycosidic link in conjunction with maltose, be that glucose is combined into trisaccharide maltose by α-(1 → 4) glycosidic link, two ends again with α-(1 → 6)-glycosidic link with other trisaccharide maltose combination, macromolecule polysaccharide so repeatedly is formed by connecting.
The preparation method's of trisaccharide maltose of the present invention implementation procedure is as follows:
1, in 250 milliliters of round-bottomed flasks, pulullan polysaccharide (pullulan) 15g is dissolved in the mixed solution of diacetyl oxide 50ml and pyridine 75ml, place 60 ℃ thermostatic bath to stir two days, with solvent evaporated under reduced pressure on the BUCHI Rotary Evaporators, pour the thickness colloid of this evaporate to dryness into dilute hydrochloric acid (1N then, 300ml) stir after 30 minutes in the aqueous solution, suction filtration, use massive laundering, and wash with saturated saturated solution of sodium bicarbonate, till weakly alkaline, 50 ℃ of oven dry are down pulverized to such an extent that the Powdered full acetyl pullulan polysaccharide crude product 23 of white solid restrains (the about 60-80% of content).
2, in 100 milliliters of round-bottomed flasks, above-mentioned full acetyl pullulan polysaccharide 15 grams are dissolved in (volume ratio) in the solution of acetic anhydride that contains 5% vitriol oil, also available Zinc Chloride Anhydrous or trifluoroacetic acid, content 1%-10%, place 40 ℃ thermostatic bath to stir three days, after pour in the 300ml frozen water, with ethyl acetate extraction three times, again with saturated sodium bicarbonate washing extraction, until neutrality.Concentrate back column chromatography gradient separations, carry out rough segmentation at 2: 1 with ethyl acetate/petroleum ether earlier, separate as eluent with ethyl acetate/petroleum ether 1: 1 again, detect, can get the pure product 5.5 of full acetyl trisaccharide maltose and restrain (content is greater than 98%) with thin-layer chromatography (TLC).The intact raw material of unreacted can reclaim as eluent with ethyl acetate/methanol 4: 1.
3, the full acetyl pullulan polysaccharide of 30 grams was dissolved in the mixing solutions that contains the vitriol oil, glacial acetic acid and diacetyl oxide volume ratio 1: 10: 20, reacted 7 days down at 0 ℃, after pour in the 400ml water with ethyl acetate extraction three times, again with saturated sodium bicarbonate washing extraction, until neutrality.Concentrate back column chromatography gradient separations, carry out rough segmentation at 2: 1 with ethyl acetate/petroleum ether earlier, separate as eluent with ethyl acetate/petroleum ether 1: 1 again, full acetyl trisaccharide maltose 10 restrains.
4, taking off the acetyl condition is under the room temperature, sodium methylate-methanol solution of methanol solution that ammonia is saturated or pH value 9-10 (corresponding power 5), promptly, in 250 milliliters of round-bottomed flasks, full acetyl trisaccharide maltose 5 grams are dissolved in 100 milliliters of anhydrous methanols, sodium methylate-the methanol solution that adds 1N is to pH10, and reaction is 10 hours under the room temperature, Zeo-karb (Amberlitel20H
+) after the neutralization, evaporated under reduced pressure gets trisaccharide maltose crude product (content is greater than 90%).
5, with above-mentioned trisaccharide maltose crude product 3 grams, be dissolved in 2 ml waters, on sephadex G 25 posts with deionization water as solvent desalting purifying, the moving phase that contains trisaccharide maltose gets the pure product of trisaccharide maltose (under anti-phase high-pressure liquid phase standard conditions, purity is greater than 99.5%) after the lyophilize under standard method.
Claims (5)
1, a kind of preparation method of trisaccharide maltose, its method may further comprise the steps:
1) the exocellular polysaccharide pulullan polysaccharide that is produced by the mould fermentation of the falx that sprouts is a raw material, utilize α in the pulullan polysaccharide-(1 → 6)-glucoside bond to be easy to fracture than α-(1 → 4)-glucoside bond, make it in acid and acetic anhydride mixed solution acetolysls to take place, acid with the ratio of acetic anhydride is: 1: 100-1: 10; Temperature of reaction is-10 ℃-+50 ℃ and obtains full acetylated trisaccharide maltose;
2) fall ethanoyl with the base strength hydrolysis of pH=9-10;
3) make the pure product of trisaccharide maltose through common reversed phase column chromatography process.
2, preparation method according to claim 1 is characterized in that: described acetolysls contains glacial acetic acid, and it is 10-50% that content can reach volume ratio.
3, preparation method according to claim 1 is characterized in that: described acid is a kind of of the vitriol oil, Zinc Chloride Anhydrous, trifluoroacetic acid.
4, preparation method according to claim 1 is characterized in that: described acid is the mixture of a kind of and glacial acetic acid of the vitriol oil, Zinc Chloride Anhydrous, trifluoroacetic acid.
5, preparation method according to claim 1 is characterized in that: it is ammonia is saturated under the room temperature methanol solution or sodium methylate-methanol solution of pH value 9-10 that the ethanoyl condition is fallen in described hydrolysis.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510013106 CN1680571A (en) | 2005-01-17 | 2005-01-17 | Preparation of maltotriose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200510013106 CN1680571A (en) | 2005-01-17 | 2005-01-17 | Preparation of maltotriose |
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| CN1680571A true CN1680571A (en) | 2005-10-12 |
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| CN 200510013106 Pending CN1680571A (en) | 2005-01-17 | 2005-01-17 | Preparation of maltotriose |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101438782B (en) * | 2008-12-31 | 2011-04-13 | 保龄宝生物股份有限公司 | Moisture-keeping syrup and preparation method thereof |
| CN105713051A (en) * | 2014-12-04 | 2016-06-29 | 中国科学院生态环境研究中心 | Novel preparation method of maltotriose |
| US10568839B2 (en) | 2011-01-11 | 2020-02-25 | Capsugel Belgium Nv | Hard capsules |
| US11319566B2 (en) | 2017-04-14 | 2022-05-03 | Capsugel Belgium Nv | Process for making pullulan |
| US11576870B2 (en) | 2017-04-14 | 2023-02-14 | Capsugel Belgium Nv | Pullulan capsules |
-
2005
- 2005-01-17 CN CN 200510013106 patent/CN1680571A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101438782B (en) * | 2008-12-31 | 2011-04-13 | 保龄宝生物股份有限公司 | Moisture-keeping syrup and preparation method thereof |
| US10568839B2 (en) | 2011-01-11 | 2020-02-25 | Capsugel Belgium Nv | Hard capsules |
| CN105713051A (en) * | 2014-12-04 | 2016-06-29 | 中国科学院生态环境研究中心 | Novel preparation method of maltotriose |
| US11319566B2 (en) | 2017-04-14 | 2022-05-03 | Capsugel Belgium Nv | Process for making pullulan |
| US11576870B2 (en) | 2017-04-14 | 2023-02-14 | Capsugel Belgium Nv | Pullulan capsules |
| US11878079B2 (en) | 2017-04-14 | 2024-01-23 | Capsugel Belgium Nv | Pullulan capsules |
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