DE3428522A1 - Process for the preparation of water-soluble polysaccharides, the saccharides obtainable in this way, and their use - Google Patents
Process for the preparation of water-soluble polysaccharides, the saccharides obtainable in this way, and their useInfo
- Publication number
- DE3428522A1 DE3428522A1 DE19843428522 DE3428522A DE3428522A1 DE 3428522 A1 DE3428522 A1 DE 3428522A1 DE 19843428522 DE19843428522 DE 19843428522 DE 3428522 A DE3428522 A DE 3428522A DE 3428522 A1 DE3428522 A1 DE 3428522A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- polysaccharides
- soluble polysaccharides
- polyhydric alcohol
- carried out
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000004676 glycans Chemical class 0.000 title claims abstract description 19
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 19
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 16
- 150000001720 carbohydrates Chemical class 0.000 title claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 10
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 235000013305 food Nutrition 0.000 claims abstract description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 6
- 239000008103 glucose Substances 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 5
- 235000014633 carbohydrates Nutrition 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 abstract description 5
- 239000011230 binding agent Substances 0.000 abstract description 3
- 150000002482 oligosaccharides Polymers 0.000 abstract description 2
- 235000005911 diet Nutrition 0.000 abstract 1
- 230000000378 dietary effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
- 239000000600 sorbitol Substances 0.000 description 7
- 239000008101 lactose Substances 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 229930182830 galactose Natural products 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 3
- 229920002907 Guar gum Polymers 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 235000010417 guar gum Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- 102000013142 Amylases Human genes 0.000 description 2
- 108010065511 Amylases Proteins 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
- CZMRCDWAGMRECN-FBXJDJJESA-N D-sucrose Chemical compound O[C@@H]1[C@@H](O)[C@H](CO)O[C@]1(CO)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](CO)O1 CZMRCDWAGMRECN-FBXJDJJESA-N 0.000 description 1
- 101000637835 Homo sapiens Serum amyloid A-4 protein Proteins 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- 102100032016 Serum amyloid A-4 protein Human genes 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- 229920001938 Vegetable gum Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-PQMKYFCFSA-N alpha-D-mannose Chemical compound OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-PQMKYFCFSA-N 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 102000005936 beta-Galactosidase Human genes 0.000 description 1
- 108010005774 beta-Galactosidase Proteins 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004186 food analysis Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- -1 polytetrafluoroethylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
- A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
- A23L33/24—Cellulose or derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
- A23G2200/06—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing beet sugar or cane sugar if specifically mentioned or containing other carbohydrates, e.g. starches, gums, alcohol sugar, polysaccharides, dextrin or containing high or low amount of carbohydrate
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Verfahren zur ITerstellung von wasserlöslichen Polysaccha-Process for the production of water-soluble polysaccha
rinden, die so erhältlichen Saccharide und ihre Verwendung Zusatz ur Patentanmeldung P 34 23 421 .7 Die llauptanmeldung betrifft ein Verfahren zur Herstellung von aus Anhydroglucose aufgebauten, wasserlöslichen Polysacchariden durch Umsetzung von Glucose oder diese als Monomer-Baustein enthaltenden Kohlenhydraten mit mehrwertigen Alkoholen und einer Säure, das dadurch gekennzeichnet ist, daß Fluorwasserstoff als Säure und gegebenenfalls gleichzeitig als Lösemittel verwendet wird, weiterhin wasserlösliche, von Glucose abgeleitete Polysaccharide, gekennzeichnet durch einen Gehalt an einem mehrwertigen Alkohol, sowie die Verwendung dieser Polysaccharide als Wasserbinde- bzw. Wasserrückhaltemittel, insbesondere in Lebensmitteln.rinden, the saccharides obtainable in this way and their use additive ur patent application P 34 23 421 .7 The main application relates to a method for Production of water-soluble polysaccharides composed of anhydroglucose by converting glucose or carbohydrates containing it as a monomer component with polyhydric alcohols and an acid, which is characterized in that Hydrogen fluoride is used as an acid and optionally at the same time as a solvent is, furthermore, water-soluble, glucose-derived polysaccharides characterized by a content of a polyhydric alcohol, as well as the use of these polysaccharides as a water binding agent or water retention agent, especially in food.
Es wurde nun gefunden, daß man in derselben Weise auch wasserlösliche Polysaccharide herstellen kann, die nicht oder nicht ausschließlich aus Anhydroglucose aufgebaut sind. Die so erhaltenen Produkte sind neu und ebenfalls Gegenstand der Erfindung, ebenso ihre Verwendung als Wasserbinle- bzw. Wasserrückhaltemittel, insbesondere in Lebensmitteln.It has now been found that water-soluble ones can also be obtained in the same way Can produce polysaccharides which are not or not exclusively from anhydroglucose are constructed. The products obtained in this way are new and are also the subject of Invention, as well as their use as a water binding agent or water retention agent, in particular in food.
Eine besondere Ausgestaltung der Erfindung besteht darin, daß die Uuisetzung ohne Zusatz des mehrwertigen Alkohols durchgeführt wird. Auch die so erhaltenen Produkte lassen sich für die gleichen Zwecke versenden.A particular embodiment of the invention is that the Uuisetzung is carried out without the addition of polyhydric alcohol. Also like that received products can be sent for the same purposes.
Weitere, insbesondere bevorzugte Ausgestaltungen der Erfindung sind in den Patentansprüchen niedergelegt.Further, particularly preferred embodiments of the invention are laid down in the claims.
Erfindungsgemäß werden somit wasserlösliche Polysaccharide hergestellt, die im Falle eines Gehaltes von Anhydroglucose noch andere Zucker-Monomer-Bausteine enthalten oder ausschließlich aus von Anhydroglucose verschiedenen Monomer- Bausteinen aufgebaut sind. Als Ausgangsmaterialien kommen dementsprechend, gegebenfalls neben den gemäß Hauptanmeldung eingesetzten Verbindungen, in Betracht: Monosaccharide wie Galactose oder Mannose, Oligosaccharide wie Lactose, Saccharose oder Raffinose sowie Polysaccharide wie Guaran oder andere Pflanzengummen.According to the invention, water-soluble polysaccharides are thus produced, which, in the case of anhydroglucose content, also contain other sugar-monomer components contain or consist exclusively of monomers other than anhydroglucose Building blocks are constructed. As starting materials come accordingly, if necessary in addition the compounds used according to the main application, into consideration: monosaccharides such as galactose or mannose, oligosaccharides such as lactose, sucrose or raffinose as well as polysaccharides such as guar or other vegetable gums.
Die Schlüsselsubstanz des Stoffwechsels, die Glucose, ist somit in den Verfahrensprodukten - im Vergleich zu den Produkten der Hauptanmeldung - in verringertem Maße oder überhaupt nicht enthalten, was bei der Bildung statistisch verknüpfter Polysaccharide zu Produkten mit weiter erniedrigter Verdaulichkeit führen kann.The key substance of metabolism, glucose, is thus in the process products - compared to the products of the main application - in to a lesser extent or not at all, which is statistically important in the formation linked polysaccharides lead to products with further reduced digestibility can.
Als- mehrwertige Alkohole, die entsprechend der vorliegenden Erfindung auch entfallen können, kommen die gleichen Verbindungen wie in der Hauptanmeldung in Betracht.As- polyhydric alcohols according to the present invention can also be omitted, the same connections come as in the main application into consideration.
Die Durchführung des erfindungsgemäßen Verfahrens und die Isolierung der Verfahrensprodukte erfolgen wie in der Hauptanmeldung beschrieben.The implementation of the process according to the invention and the isolation of the process products are carried out as described in the main application.
Die Erfindung wird in den folgenden Beispielen näher erläutert: Beispiel 1 In einem zylindrischen Rührkessel aus Edelstahl. wurden 400 g trockener, flüssiger Fluorwasserstoff auf -25"C abgekühlt und unter weiterer Außenkühlung ein Gemisch aus 200 g D-(+)-Galactose und 2 g Sorbit so eingetragen, daß die Innentemperatur +0°C erreichte. Dann wurde die Kühlung entfernt und bei einer Innentemperatur von +5 bis +12"C 1 Std. nachgerührt. Danach wurde das Kühlbad durch ein Wasserbad von +40"C erst, ein solegespeister absteigender Edelstahlkühler aufgesetzt, der in eine Trockeneis-gekühlte Vorlage mündete, und ein zum raschen Abdestillieren des Fluorwasserstoffs ausreichendes Vakuum angelegt. Dieses Vakuum wurde im Lauf der Zeit verbessert, um eine hohe Destillationsgeschwindigkeit aufrechtzuerhalten. Auf diese Weise wurden in einer Stunde 550 g Fluorwasserstoff zurückgewonnen. Der Rückstand im Reaktor wurde in 1 1 kaltem Wasser unter Rühren und mäßiger Kühlung gelöst nach 30 min mit festem technischem Calciumhydroxid schwach alkalisch gestellt und nach weiteren 30 min durch Einwerfen von Trockeneis neutralisiert. Die so erhaltene Suspension wurde durch ein Bett aus Filterhilfsmittel abgesaugt und das klare, nur schwach gefärbte Filtrat gefriergetrocknet. Man erhielt einen fast farblosen Feststoff in einer Ausbeute von 90 , bezogen auf die eingesetzte Stärke.The invention is explained in more detail in the following examples: Example 1 In a cylindrical stainless steel stirred tank. 400 g became drier, more fluid Hydrogen fluoride cooled to -25 "C and a mixture with further external cooling from 200 g of D - (+) - galactose and 2 g of sorbitol entered so that the internal temperature + 0 ° C reached. Then the cooling was removed and at an internal temperature of Stirred at +5 to +12 "C for 1 hour. The cooling bath was then replaced by a water bath from +40 "C first, a brine-fed descending stainless steel cooler is put on, which is in a Dry-ice-chilled template flowed, and a quick one Distill off sufficient vacuum applied to the hydrogen fluoride. This vacuum was in the barrel improves over time to maintain a high rate of distillation. In this way, 550 g of hydrogen fluoride were recovered in one hour. Of the The residue in the reactor was dissolved in 1 l of cold water with stirring and moderate cooling dissolved after 30 min with solid technical calcium hydroxide made weakly alkaline and after a further 30 minutes neutralized by throwing in dry ice. The thus obtained Suspension was sucked through a bed of filter aid and the clear, only pale colored filtrate freeze-dried. An almost colorless solid was obtained in a yield of 90, based on the starch used.
Reg. Endgruppengehalt: 5,9 % [α]D20 (c= 10, H2O)= + 167,1° Beispiel 2 In einer Apparatur und nach dem Verfahren, wie in Beispiel 1 beschrieben, wurden 200 g D-(+)-Mannose und 2 g Sorbit mit und in 400 g HF umgesetzt. Die Ausbeute an gefriergetrocknetem Polysaccharid betrug 85 % der eingesetzten Mannose.Reg. End group content: 5.9% [α] D20 (c = 10, H2O) = + 167.1 ° Example 2 In an apparatus and according to the method as described in Example 1, were 200 g of D - (+) - mannose and 2 g of sorbitol reacted with and in 400 g of HF. The yield at Freeze-dried polysaccharide accounted for 85% of the mannose used.
Red. Endgruppengehalt: 2,4 % [α]D20 (c= 10, H2O)= + 62,2° Beispiel 3 In einer Apparatur und nach dem Verfahren wie in Beispiel 1 beschrieben, wurden 200 g Lactose und 2 g Sorbit mit und in 400 g HF umgesetzt. Die Ausbeute an gefriergetrocknetem Polysaccharid betrug 90 der eingesetzten Lactose.Red. End group content: 2.4% [α] D20 (c = 10, H2O) = + 62.2 ° Example 3 In an apparatus and according to the method as described in Example 1, were 200 g lactose and 2 g sorbitol reacted with and in 400 g HF. The yield of freeze-dried Polysaccharide was 90% of the lactose used.
Red. Endgruppengehalt: 6,1 % [α]D20 (c= 10, H2O)= + 142,9° Beispiel 4 In einer Apparatur und nach dem Verfahren wie in Beispiel 1 beschreiben, wurden 200 g Guaran (Meypro - Guar/ CSAA M - 225) und 2 g Sorbit mit und in 400 g HF umgesetzt. Die Ausbeute an gefriergetrocknetem Polysaccharid betrug 90 ffi des eingesetzten Guarans.Red. End group content: 6.1% [α] D20 (c = 10, H2O) = + 142.9 ° example 4 In an apparatus and according to the method as described in Example 1, were 200 g guaran (Meypro - Guar / CSAA M - 225) and 2 g sorbitol reacted with and in 400 g HF. The yield of freeze-dried polysaccharide was 90 ffi of that used Guarans.
Red. Endgruppengehalt: 9,7 % [α]D20 (c= 10, H2O)= + 88,2° Beispiel 5 In einer Apparatur und nach dem Verfahren wie in Beispiel 1 beschrieben, wurden 200 g D-(+)-Saccharose und 2 g Sorbit mit und in 400 g HF umgesetzt. Die Ausbeute an gefriergetrocknetem Polysaccharid betrug 92 ß der eingesetzten Saccharose.Red. End group content: 9.7% [α] D20 (c = 10, H2O) = + 88.2 ° Example 5 In an apparatus and according to the method as described in Example 1, were 200 g of D - (+) - sucrose and 2 g of sorbitol reacted with and in 400 g of HF. The yield of freeze-dried polysaccharide was 92 ß of the sucrose used.
Red. Endgruppengehalt: 3,7 % [α]D20 (c= 10, H2O)= + 28,8° Beispiel 6 Die Reaktion. wird in einer 650 ml-Polytetrafluorethylen-Vakuum-Destillationsapparatur durchgeführt. Zu dem vorgelegten auf 0°C vorgekühlten, flüssigen Fluorwasserstoff (300 g) werden unter Rühren 115 g wasserfreie Mannose und 12,9 g Sorbit (10 , bezogen auf Gesamt-Edukt) gegeben und das Gemisch 1 h bei 20°C gerührt (Magnetrührung).Red. End group content: 3.7% [α] D20 (c = 10, H2O) = + 28.8 ° Example 6 The response. is in a 650 ml polytetrafluoroethylene vacuum distillation apparatus carried out. To the submitted liquid hydrogen fluoride, which has been pre-cooled to 0 ° C (300 g), 115 g of anhydrous mannose and 12.9 g of sorbitol (10) are obtained with stirring on total starting material) and the mixture was stirred at 20 ° C. for 1 h (magnetic stirring).
Unter Erwärmen auf 50 - 60°C und Rühren wird bei langsam verbessertem Vakuum der Pluorwasserstoff abdestilliert, der Hauptteil bei vollem Wasserstrahlvakuum. Nach 1,5 -2,5 h sind etwa 90 - 95 % des eingesetzten Fluorwasserstoffs entfernt. Man erhält ca. 150 - 160 g eines Wasser hellen Sirups. Dieser wird in 300 ml Wasser aufgenommen, mit festem Calciumcarbonat unter Rühren neutralisiert, das ausgefällte Calciumfluorid abzentrifugiert und der Überstand mit einem Filterhilfsmittel filtriert.Warming to 50 - 60 ° C and stirring slowly improves the temperature The hydrogen fluoride is distilled off in a vacuum, the main part under full water-jet vacuum. After 1.5-2.5 hours, about 90-95% of the hydrogen fluoride used has been removed. About 150-160 g of a water-light syrup are obtained. This is in 300 ml of water added, neutralized with solid calcium carbonate while stirring, the precipitated Calcium fluoride centrifuged off and the supernatant with a filter aid filtered.
Die wasserhelle Lösung wird auf ein Volumen von etwa 200 ml eingeengt und über Nacht gefriergetrocknet. Man erhält 104 g farbloses, amorphes nur wenig hygroskopisches Pulver (81,3 Gew.-%).The water-white solution is concentrated to a volume of about 200 ml and freeze dried overnight. 104 g of colorless, amorphous material are obtained only slightly hygroscopic powder (81.3% by weight).
Red. Endgruppengehalt: 3,6 % [α]D20 (c= 10, H2O)= + 46,1° Beispiele 7 - 10 Entsprechend dem in Beispiel z beschriebenen Vorgehen werden verschiedene Mono- bzw. Disaccharide in flüssigem Fluorwasserstoff umgesetzt. Die Einzeldaten sind in Tabelle 1 wiedergegeben.Red. End group content: 3.6% [α] D20 (c = 10, H2O) = + 46.1 ° Examples 7 - 10 According to the procedure described in example z, various Mono- or disaccharides implemented in liquid hydrogen fluoride. The individual data are shown in Table 1.
Tabelle 1 Angaben zu den Versuchen mit verschiedenen Kohlenhydraten Bsp. Edukt Einsatz- Polyalkohol HF-Menge Produkt Ausbeute Red. Endgr.- [α]D20 menge [g] (Sorbit) [g] [g] [g] [% v. Einsatz] geh. [%] (c= 10, H2O) 7 Lactose 118 6,2 290 96 77,3 4,8 + 133,0° 8 Saccharose 110 12,3 290 106 86,7 6,9 + 27,6° 9 Galactose 118,5 6,2 290 94 75,4 5,2 + 141,8° 10 Galactose 136 - 320 99 72,8 4,6 + 164,0° Beispiel 11 Als Maß für die enzymatische in vivo-Abbaubarkeit der erfindungsgemäßen Produkte wird das Verhalten gegenüber den körpereigenen Enzymen Amylase/Amyloglucosidase (Behandlung A) und ß-Galactosidase (Behandlung B) in vitro überprüft (vgl. P. Präve et al., Handbuch der Biotechnologie, Akadem. Verlagsanstalt, Wiesbaden 1S82, S.403 f., sowie Methoden der enzymatischen Lebensmittelanalytik, Boehringer Mannheim 1983). Jeweils zu Beginn der Messung und nach 6 bzw. 1 Stunde werden enzymatische Monosaccharid-Bestimmungen von Glucose bzw. Galactose durchgeführt (Lit. vgl.Table 1 Information on the experiments with different carbohydrates Ex. Educt Feed polyalcohol HF amount Product Yield Red. Final size- [α] D20 amount [g] (sorbitol) [g] [g] [g] [% v. Use] go. [%] (C = 10, H2O) 7 lactose 118 6.2 290 96 77.3 4.8 + 133.0 ° 8 sucrose 110 12.3 290 106 86.7 6.9 + 27.6 ° 9 galactose 118.5 6.2 290 94 75.4 5.2 + 141.8 ° 10 galactose 136 - 320 99 72.8 4.6 + 164.0 ° example 11 As a measure of the enzymatic in vivo degradability of the products according to the invention the behavior towards the body's own enzymes amylase / amyloglucosidase (Treatment A) and ß-galactosidase (Treatment B) checked in vitro (see P. Preve et al., Handbuch der Biotechnologie, Akadem. Publishing house, Wiesbaden 1S82, p.403 f., as well as methods of enzymatic food analysis, Boehringer Mannheim 1983). At the beginning of the measurement and after 6 or 1 hour, enzymatic monosaccharide determinations are made carried out by glucose or galactose (lit.
oben; als Standards werden Kartoffelstärke und ein literaturbekanntes Schmelzkondensat - vgl. brit. Patentschrift 1 262 842 - bzw. Lactose verwendet), deren Ergebnisse in Tab. 2 wiedergegeben sind. above; Potato starch and a well-known literature are used as standards Melt condensate - see British patent specification 1 262 842 - or lactose used), the results of which are shown in Table 2.
Tab. 2: In vitro-Abbau der erfindungsgemäSen Produkte durch Amylase/Amyloglucosidase (A)- bzw. B-Galactosidase (B) -Behandlung Beispiel A: Glucose-Konz. in [%] B: Galactose-Konz. in [%] (Edukt) Ausgangs- Endwert Ausgangs- ~ Endwert 1 (Gal) - - 1,50 1,98 3 (Lac) 0,6 2,7 0,44 0,92 4 (Guaran) 0,95 1,08 5 (Sac) 0,3 8,0 7 (Lac) 0,88 3,62 0,75 0,74 8 (Sac) 1,56 8,27 9 (Gal) - - 2,51 2,93 10 (Gal) - - 2,04 2,10 Kartoffelstärke 0,01 76,0 Schmelzkondensat 3,9 12,5 - -Lactose - - 0 99,4 Tab. 2: In vitro degradation of the products according to the invention by amylase / amyloglucosidase (A) - or B-galactosidase (B) treatment Example A: Glucose conc. in [%] B: galactose conc. in [%] (educt) Initial final value Initial final value 1 (Gal) - - 1.50 1.98 3 (Lac) 0.6 2.7 0.44 0.92 4 (Guaran) 0.95 1.08 5 (Sac) 0.3 8.0 7 (Lac) 0.88 3.62 0.75 0.74 8 (Sac) 1.56 8.27 9 (Gal) - - 2.51 2.93 10 (Gal) - - 2.04 2.10 Potato starch 0.01 76.0 Melt condensate 3.9 12.5 - -Lactose - - 0 99.4
Claims (8)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843428522 DE3428522A1 (en) | 1984-08-02 | 1984-08-02 | Process for the preparation of water-soluble polysaccharides, the saccharides obtainable in this way, and their use |
| AT85107545T ATE60064T1 (en) | 1984-06-26 | 1985-06-19 | PROCESS FOR THE PRODUCTION OF WATER-SOLUBLE POLYSACCHARIDS, THE SACCHARIDS SO AVAILABLE AND THEIR USE. |
| EP85107545A EP0166362B1 (en) | 1984-06-26 | 1985-06-19 | Process for preparaing water soluble polysaccharides, saccharides so obtained and their application |
| DE8585107545T DE3581320D1 (en) | 1984-06-26 | 1985-06-19 | METHOD FOR THE PRODUCTION OF WATER-SOLUBLE POLYSACCHARIDES, THE SACCHARIDES SO AVAILABLE AND THEIR USE. |
| AU44160/85A AU4416085A (en) | 1984-06-26 | 1985-06-25 | Preparation of water soluble poly saccharides |
| CA000485203A CA1240988A (en) | 1984-06-26 | 1985-06-25 | Process for the preparation of water-soluble polysaccharides, the saccharides thus obtainable, and their use |
| DK287585A DK287585A (en) | 1984-06-26 | 1985-06-25 | WATER SOLUBLE POLYSACCHARIDES, THEIR PREPARATION AND APPLICATION |
| US06/748,934 US4766207A (en) | 1984-06-26 | 1985-06-26 | Process for the preparation of water-soluble polysaccharides, the saccharides thus obtainable, and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843428522 DE3428522A1 (en) | 1984-08-02 | 1984-08-02 | Process for the preparation of water-soluble polysaccharides, the saccharides obtainable in this way, and their use |
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| DE3428522A1 true DE3428522A1 (en) | 1986-02-13 |
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| DE19843428522 Withdrawn DE3428522A1 (en) | 1984-06-26 | 1984-08-02 | Process for the preparation of water-soluble polysaccharides, the saccharides obtainable in this way, and their use |
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1984
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