The present application relates to a novel allulose-derived compound and an acid-resistant allulose composition comprising the same.
[2]
background
[3]
Allulose is a natural sugar present in very small amounts in molasses, raisins, and figs, and is a monosaccharide with 70% sweetness compared to sugar. Unlike fructose or sugar, allulose is not metabolized in the human body, so it has almost no calories, and it has been reported to inhibit body fat formation (Matuo, T. et. al., Asia Pac. J.Clin. Nutr., 10, 233-237, 2001; Matsuo, T. and K. Izumori, Asia Pac. J. Clin. Nutr., 13, S127, 2004). In addition, it has no effect on blood sugar and has been in the spotlight as a substitute for sugar as it has been announced that it has non-caries and anti-caries functions.
[4]
On the other hand, it is disclosed that allulose-derived substances can be confirmed limitedly through gas chromatography (GC) (WO2018/127669). However, since such an allulose-derived material is not separated by liquid chromatography (LC), it is difficult to confirm the properties in detail.
[5]
DETAILED DESCRIPTION OF THE INVENTION
technical challenge
[6]
After intensive research efforts on allulose-derived materials, the present inventors isolated a novel allulose disaccharide for the first time in the allulose manufacturing process, and found that the novel disaccharide has superior acid resistance compared to the existing disaccharide, thereby completing the present application.
[7]
means of solving the problem
[8]
An object of the present application is to provide a compound in which two molecules of allulose are linked by a glycosidic bond.
[9]
Another object of the present application is to provide an acid-resistant allulose composition comprising the compound and the monosaccharide allulose.
[10]
Another object of the present application is to provide a composition for additives for food containing the compound.
[11]
Effects of the Invention
[12]
Since the novel allulose disaccharide of the present application exhibits excellent acid resistance compared to sugar, which is another isomer having a similar structure, it can be used as a sugar substitute in a food composition as well as usefully used in various industrial fields.
[13]
Brief description of the drawing
[14]
1 shows the structure and carbon numbering of allulose.
[15]
2 is an HPLC chromatogram analyzed by column- (Biorad Aminex HPX-87C) of disaccharides produced during the preparation of allulose.
[16]
FIG. 3 is an HPLC chromatogram of D1 and D2 analyzed by column (YMC Pack Polyamine II) of a mixture of disaccharides produced during the preparation of allulose by column (YMC Pack Polyamine II).
[17]
4 shows the three-dimensional structure of D1, an allulose disaccharide having excellent acid resistance.
[18]
Best mode for carrying out the invention
[19]
A detailed description of this is as follows. Meanwhile, each description and embodiment disclosed in the present application may be applied to each other description and embodiment. That is, all combinations of the various elements disclosed in this application fall within the scope of this application. In addition, it cannot be seen that the scope of the present application is limited by the specific descriptions described below.
[20]
In addition, those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific aspects of the present application described herein. Also, such equivalents are intended to be covered by this application.
[21]
[22]
One aspect of the present application provides a compound in which two molecules of allulose are linked by a glycosidic bond.
[23]
In the present application, the term "allulose" is a compound also known as "psicose" or "psicose", and refers to a C-3 epimer of fructose, a type of ketohexose.
[24]
The allulose molecule of the present application may have a linear or cyclic structure, and the carbon numbering may be in the order close to the ketone group, as is known in the art, so that the carbon having the ketone group may be numbered as carbon #2. In one embodiment, carbons of allulose of the present application may be numbered as shown in FIG. 1 .
[25]
Allulose of the present application may be extracted from a natural product or prepared by a chemical synthesis method or a biological method using an enzyme, but is not limited thereto.
[26]
Allulose of the present application may be L-form or D-form, and both molecules of allulose may be L-form or D-form, or L-form and D-form, respectively.
[27]
When the allulose is in a state in which it is not bound to other allulose molecules or other saccharides, it may be referred to as "monosaccharide allulose", "allulose monosaccharide", "allulose monosaccharide", or "allulose", but is limited thereto. doesn't happen
[28]
[29]
In the present application, the term "glycosidic bond" refers to an ether-type bond formed between a hemiacetal hydroxy group of a sugar and a functional group such as various alcohols, phenols, carboxylic acids, and aldehydes. Specifically, two monosaccharide molecules are converted into disaccharides. It may be a bond used to bond.
[30]
[31]
In the present application, the term “compound in which two molecules of allulose are linked by a glycosidic bond” may be used interchangeably with terms such as “allulose disaccharide”, “allulose dimer”, and “disaccharide allulose”.
[32]
Specifically, in the allulose disaccharide, one molecule of two molecules of allulose is cyclic allulose, and the hydroxyl group on carbon 2 of the cyclic allulose is any one of carbons 1 to 6 of the other allulose molecule It may be a compound connected by a glycosidic bond between the hydroxyl groups of the carbons of The number of glycosidic bonds may be 1 to 2, specifically, 1 may be.
[33]
In one embodiment, the bond may be a glycosidic bond between a hydroxyl group on carbon 2 of cyclic allulose and a hydroxyl group on carbon 6 of another allulose.
[34]
In one embodiment, one molecule of the two molecules of allulose may be in the form of psicofuranose, and the other molecule may be in the form of psicopyranose, and in one embodiment, one represented by the following Chemical Formula 1 can, but is not limited thereto.
[35]
[Formula 1]
[36]

[37]
In one embodiment, the allulose disaccharide may be one represented by the following Chemical Formula 2, but is not limited thereto.
[38]
[Formula 2]
[39]

[40]
In one embodiment, the allulose disaccharide of the present application is 2-(hydroxymethyl)-2-((3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methyl oxy)tetrahydro-2H-pyran-3,4,5-triol(2-(hydroxymethyl)-2-((3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetrahydro -2H-pyran-3,4,5-triol), and more specifically (2S,3R,4R,5R)-2-(hydroxymethyl)-2-(((2R,3S) ,4R)-3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol ((2S) ,3R,4R,5R)-2-(hydroxymethyl)-2-(((2R,3S,4R)-3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetrahydro-2H -pyran-3,4,5-triol) may be a compound named, but is not limited thereto.
[41]
(2S,3R,4R,5R)-2-(hydroxymethyl)-2-(((2R,3S,4R)-3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydro Furan-2-yl) methoxy) tetrahydro-2H-pyran-3,4,5-triol is 6-O-β-D-psychopyranosyl-α-D-psycho, depending on the form of psychofuranose Furanose (6-O-β-D-Psicopyranosyl-α-D-psicofuranose) or 6-O-β-D-Psycopyranosyl-β-D-Psicopyranosyl- β-D-psicofuranose) may be generically named. Specifically, the structure of 6-O-β-D-psychopyranosyl-α-D-psychofuranose is represented by the following Chemical Formula 3, and the structure of 6-O-β-D-psychopyranosyl-β-D-psychopuranoose is can be represented by the following formula (4).
[42]
[Formula 3]
[43]

[44]
[Formula 4]
[45]

[46]
Also the above (2S,3R,4R,5R)-2-(hydroxymethyl)-2-(((2R,3S,4R)-3,4,5-trihydroxy-5-(hydroxymethyl)tetra Hydrofuran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol is (2S,3R,4R,5R)-2-(hydroxymethyl)-2-((((2S,3R,4R,5R)-2-(hydroxymethyl)-2-((( 2R,3S,4R,5S)-3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5- Triol ((2S,3R,4R,5R)-2-(hydroxymethyl)-2-(((2R,3S,4R,5S)-3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2- yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol), or (2S,3R,4R,5R)-2-(hydroxymethyl)-2-((( 2R,3S,4R,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5- Triol ((2S,3R,4R,5R)-2-(hydroxymethyl)-2-(((2R,3S,4R,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2- yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol), but is not limited thereto.
[47]
The compound of the present application may have acid resistance.
[48]
In the present application, the term "acid resistance" means stability to acids (acid). Specifically, in the present application, it may mean stability that a specific compound can maintain without losing its intrinsic properties to acid. It may mean excellent acid resistance, but is not limited thereto. In one embodiment, the compound having acid resistance may have better acid resistance than a compound having an isomer relationship with the compound, and specifically may have superior acid resistance compared to sugar (sucrose), but is not limited thereto. When the compound is stored in an acidic environment, the acid resistance is specifically exposed to an environment of pH 7 or less for more than 0 hours, and the change value of purity, mass, weight, etc. with time is measured to measure the residual amount of the compound It can be evaluated by doing, but is not limited thereto.
[49]
The compound of the present application may have acid resistance under conditions of pH 0.1 to pH 7, and more specifically, pH 0.5 to pH 7, pH 0.7 to pH 7, pH 1 to pH 7, pH 1 to pH 6.7, pH 1 to pH 6.5 , pH 1.5 to pH 6.5, pH 1.5 to pH 6, pH 2 to pH 6, pH 2 to pH 5.5, pH 2 to pH 5, pH 2 to pH 4.5, or pH 2 to pH 4 may have acid resistance, It is not limited thereto.
[50]
In addition, when the compound of the present application is stored for 0 to 120 hours at pH 2 to pH 7, the residual ratio is 40 parts by weight or more compared to the initial 100 parts by weight, specifically 43, 44, 45, 46, 47, 48 , 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73 , 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, or 98 parts by weight or more, more specifically 99 parts by weight or more, and the storage time is 120 hours, 96 hours, 84 hours, 72 hours, 60 hours, 48 ​​hours, 36 hours, 24 hours, 12 hours, or 6 hours. or more, but is not limited thereto.
[51]
Another aspect of the present application provides a saccharide composition comprising the allulose disaccharide and allulose monosaccharide of the present application.
[52]
In the composition, the allulose disaccharide may be included in an amount greater than 0 parts by weight and not more than 20 parts by weight, based on 100 parts by weight of the total weight of allulose disaccharide and allulose monosaccharide, specifically 15 parts by weight or less, 13 parts by weight or less, 11 parts by weight or less , 10 parts by weight or less, 9 parts by weight or less, 8 parts by weight or less, 7 parts by weight or less, 6 parts by weight or less, 5 parts by weight or less, 4 parts by weight or less, 3 parts by weight or less, 2.5 parts by weight or less, 2 parts by weight or less , 1.5 parts by weight or less, 1 parts by weight or less, 0.7 parts by weight or less, 0.6 parts by weight or less, 0.5 parts by weight or less, 0.4 parts by weight or less, 0.3 parts by weight or less, 0.2 parts by weight or less, 0.1 parts by weight or less, 0.0001 parts by weight or less , or 0.001 parts by weight or less and/or more than 0 parts by weight, 0.1 parts by weight or more, 0.5 parts by weight or more, 0.7 parts by weight or more, 1 parts by weight or more, 1.5 parts by weight or more, 2 parts by weight or more, or 3 parts by weight or more. may include, but are not limited to.
[53]
In addition, the composition of the present application may exist in a crystalline form or a liquid form, and the content of allulose disaccharide in the composition may vary depending on the form. Specifically, when the composition of the present application is in a crystalline form, the allulose disaccharide in the composition is 5 parts by weight or less, 4 parts by weight or less, 3 parts by weight or less, 2.5 parts by weight or less based on 100 parts by weight of the total weight of disaccharide and monosaccharide allulose , 2 parts by weight or less, 1.5 parts by weight or less, 1 part by weight or less, 0.7 parts by weight or less, 0.6 parts by weight or less, 0.5 parts by weight or less, 0.4 parts by weight or less, 0.3 parts by weight or less, 0.2 parts by weight or less, 0.1 parts by weight or less , 0.05 parts by weight or less, 0.005 parts by weight or less, 0.001 parts by weight or less, 0.0005 parts by weight or less or 0.0001 parts by weight or less and/or more than 0 parts by weight, 0.1 parts by weight or more, 0.5 parts by weight or more, 0.7 parts by weight or more, 1 weight It may be included in parts by weight or more, 1.5 parts by weight or more, 2 parts by weight or more, or 3 parts by weight or more, but is not limited thereto.
[54]
When the composition of the present application is in a liquid form, the allulose disaccharide in the composition is 15 parts by weight or less, 13 parts by weight or less, 11 parts by weight or less, 10 parts by weight or less, 9 parts by weight based on 100 parts by weight of the total weight of the disaccharide and monosaccharide allulose parts by weight or less, 8 parts by weight or less, 7 parts by weight or less, 6 parts by weight or less, 5 parts by weight or less, 4 parts by weight or less, 3 parts by weight or less, 2.5 parts by weight or less, 2 parts by weight or less, 1.5 parts by weight or less, 1 weight parts by weight or less, 0.7 parts by weight or less, 0.6 parts by weight or less, 0.5 parts by weight or less, 0.3 parts by weight or less, 0.2 parts by weight or less, 0.1 parts by weight or less, 0.05 parts by weight or less, 0.005 parts by weight or less, 0.001 parts by weight or less, 0.0005 weight parts by weight or less or 0.0001 parts by weight or less and/or more than 0 parts by weight, 0.1 parts by weight or more, 0.5 parts by weight or more, 0.7 parts by weight or more, 1 parts by weight or more, 1.5 parts by weight or more, 2 parts by weight or more, or 3 parts by weight or more. may be included, but is not limited thereto.
[55]
[56]
Another aspect of the present application provides a food composition comprising the allulose disaccharide of the present application.
[57]
The food composition of the present application includes, but is not limited to, general food, health food and medical (or patient) food composition. Specifically, the food composition of the present application is a beverage (eg, dietary fiber beverage, carbonated water, wheat flour, tea, etc.), alcoholic beverage, bakery, sauce (eg, ketchup, pork cutlet sauce, etc.), dairy products (eg, fermented milk, etc.), Processed meat products (eg, ham, sausage, etc.), processed chocolate products, gum, candy, jelly, ice cream, syrup, dressing, snacks (eg, cookies, crackers, etc.), pickled vegetables (eg, green, pickled fruits, red ginseng extract or red ginseng) slices, etc.), meal replacements (eg, frozen foods and HMR, etc.) or processed foods. More specifically, the food composition may be a carbonated beverage composition, but is not limited thereto.
[58]
When the allulose disaccharide of the present application is used in a food composition, the sweetener of the present application may be added as it is or used together with other food ingredients, and may be appropriately used according to a conventional method. The food composition of the present application may contain various flavoring agents or natural carbohydrates as additional ingredients. The above-mentioned natural carbohydrates are monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol and erythritol. As the sweetener, natural sweeteners such as thaumatin and stevia extract or synthetic sweeteners such as saccharin and aspartame may be used.
[59]
In addition to the above, the food composition of the present application includes various nutrients, vitamins, electrolytes, flavoring agents, colorants, pectin and salts thereof, alginic acid and salts thereof, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohol, It may contain a carbonation agent used for carbonated beverages, and the like. In addition, the food composition of the present application may contain flesh for the production of natural fruit juice, fruit juice beverage, and vegetable beverage. These components may be used independently or in combination. The ratio of these additives may be selected in the range of 0.01 to 0.20 parts by weight per 100 parts by weight of the food composition of the present application.
[60]
[61]
The novel allulose-derived compound of the present application may be used in the form of a food pharmaceutically acceptable salt.
[62]
The term "food pharmaceutically acceptable salt" in the present application may be used interchangeably with "pharmaceutically acceptable salt", and does not cause serious irritation to the organism to which the compound is administered and impairs the biological activity and properties of the compound. It means a formulation of a compound that does not The salt may refer to any salt that retains the desired biological and/or physiological activity of the compound or derivative and exhibits minimal undesired toxicological effects. In one embodiment, it may be in the form of an acid addition salt formed by a pharmaceutically acceptable free acid. Acid addition salts are prepared by conventional methods, for example by dissolving the compound in an aqueous solution of an excess of acid and precipitating the salt with a water-miscible organic solvent such as methanol, ethanol, acetone or acetonitrile. Equal molar amounts of the compound and an acid or alcohol (eg glycol monomethyl ether) in water may be heated, and then the mixture may be evaporated to dryness, or the precipitated salt may be filtered off with suction. In this case, inorganic acids and organic acids can be used as free acids, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, tartaric acid, etc. can be used as inorganic acids, and methane sulfonic acid, p-toluene sulfonic acid, acetic acid, tri Fluoroacetic acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, manderic acid, propionic acid, citric acid, lactic acid, glycolic acid ( glycollic acid), gluconic acid, galacturonic acid, glutamic acid, glutaric acid,
[63]
In addition, bases can be used to prepare pharmaceutically acceptable metal salts. The alkali metal or alkaline earth metal salt is obtained, for example, by dissolving the compound in an excess alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the undissolved compound salt, and then evaporating and drying the filtrate. In this case, as a metal salt, it is pharmaceutically suitable to prepare a sodium, potassium or calcium salt, but is not limited thereto. In addition, the corresponding silver salt can be obtained by reacting an alkali metal or alkaline earth metal salt with a suitable silver salt (eg, silver nitrate).
[64]
The pharmaceutically acceptable salts of the present application include all salts of acidic or basic groups that may be present, unless otherwise indicated. For example, food-acceptable salts may include sodium, calcium and potassium salts of hydroxy groups, and other food-acceptable salts of amino groups include hydrobromide, sulfate, hydrogen sulfate, phosphate, hydrogen phosphate, and the like. There are hydrogen phosphate, acetate, succinate, citrate, tartrate, lactate, mandelate, methanesulfonate (mesylate) and p-toluenesulfonate (tosylate) salts, and through a method for preparing salts known in the art can be manufactured.
[65]
Modes for carrying out the invention
[66]
Hereinafter, the present application will be described in more detail through Examples and Experimental Examples. However, these Examples and Experimental Examples are for illustrative purposes of the present application, and the scope of the present application is not limited to these Examples and Experimental Examples.
[67]
[68]
Example 1: Isolation of novel allulose disaccharides
[69]
In the process of preparing allulose known in Korean Patent Registration No. 10-1723007, disaccharides were separated from the stock solution before the allulose crystallization step through HPLC, unlike the prior literature (WO2018/127669). Specifically, the HPLC chromatogram analysis conditions of Table 1 below were performed, and it was confirmed that a new, unknown substance other than allulose was generated from the stock solution as shown in FIG. 2 .
[70]
Although the content of the new material separated as described above was somewhat different depending on the manufacturing process, it was present at 2% or less in the initial stock solution, and it was confirmed that it increased to a level of 5% depending on the storage time.
[71]
[72]
[Table 1]
Equipment Agilent technologies 1200 series
Column Biorad Aminex HPX-87C (7.8 X 300mm, 9um)
Eluent Water
flow rate 0.6mL/min
Temperature 80℃
RI cell temperature 35℃
[73]
As a result, allulose was confirmed at 21.1 minutes and the new material was confirmed at 31.7 minutes. Accordingly, the new material was purified to a purity of 95% or more using preparative HPLC to separate the produced new material, and the column was used. Thus, it was precisely separated again.
[74]
Specifically, HPLC chromatograms were performed.
[75]
Chromatogram separation conditions are shown in Table 2 below.
[76]
[77]
[Table 2]
Equipment Shimadzu LC 10A
Column YMC Pack Polyamine II (4.6 X 250mm, 5um,12nm)
Eluent Acetonitrile / Water (80/20)
flow rate 1mL/min
Temperature 30℃
RI cell temperature 30℃
[78]
As a result, it was confirmed that the material that appeared as one peak in the HPLC conditions of Table 1 appeared as two peaks in the separation conditions of Table 2 (FIG. 3), and the material of the peak identified at 22.5 minutes was confirmed at D1 and 17.7 minutes. The material at the peak was named D2.
[79]
[80]
Example 2: Identification of allulose disaccharides
[81]
Further analysis was performed on D1 identified in Example 1.
[82]
[83]
Major 6-O-β-D-Psicopyranosyl-α-D-psicofuranose silver, white amorphous powder, ESI-MS m/z 365 [M+Na]+; 1H NMR (850 MHz, D2O) δH 3.44 (1H, d, J = 12.0 Hz), 3.47 (1H, d, J = 12.0 Hz), 3.56 (1H, dd, J = 11.0, 5.0 Hz), 3.60 (1H) , d, J = 12.0 Hz), 3.62 (1H, dd, J = 11.0, 2.5 Hz), 3.70 (1H, br d, J = 12.5 Hz), 3.75 (1H, d, J = 12.0 Hz), 3.75 ( 1H, br ma), 3.82 (1H, br d, J = 12.5 Hz), 3.84 (1H, br s), 3.92 (1H, t, J = 3.0 Hz), 3.97 (1H, d, J = 5.5 Hz) , 4.09 (1H, t, J = 5.5 Hz), 4.13 (1H, br m) [D2O signal δH 4.70]; 13C NMR signals δC 57.6, 60.4, 62.9, 64.7, 64.9, 69.1, 68.9, 70.2, 70.3, 81.2, 101.8, 103.4.
[84]
[85]
[86]
A. Measurement of spin-spin multiplicity and coupling constant is difficult due to overlapping peaks
[87]
B. 13C NMR peak information was obtained by analyzing HSQC (850 MHz, D2O) and HMBC (850 MHz, D2O) spectral data of NMR
[88]
[89]
Minor 6-O-β-D-Psicopyranosyl-β-D-psicofuranose, white amorphous powder, ESI-MS m/z 365 [M+Na]+; 1H NMR (850 MHz, D2O) δH 3.49 (1H, d, J = 13.0 Hz), 3.73 (1H, d, J = 13.0 Hz), 3.58 (1H, ma), 3.68 (1H, dd, J = 11.0, 2.5 Hz), 3.62 (1H, ma), 3.71 (1H, br d, J = 12.0 Hz), 3.82 (1H, br d, J = 12.0 Hz), 3.76 (1H, br ma), 3.78 (1H, ma) ), 3.87 (1H, br s), 3.98 (1H, t, J = 3.0 Hz), 3.95 (1H, d, J = 4.5 Hz), 4.00 (1H, br m), 4.34 (1H, dd, J = 8.0, 4.5 Hz) [DO signal δH 4.70]; 13C NMR signals δC 57.7, 61.4, 62.2, 64.7, 64.8, 69.0, 69.2, 70.8, 74.4, 80.8, 101.8, 105.9.
[90]
[91]
A. Measurement of spin-spin multiplicity and coupling constant is difficult due to overlapping peaks
[92]
B. 13C NMR peak information was obtained by analyzing HSQC (850 MHz, D2O) and HMBC (850 MHz, D2O) spectral data of NMR
[93]
[94]
As a result, it was confirmed that D1 is a novel allulose disaccharide and has the structure of Formula 2 below.
[95]
[96]
[Formula 2]
[97]

[98]
On the other hand, D1 has two types of optical isomer structures, and specifically, in major/minor form, the stereochemistry of carbon 2 (number 5 based on IUPAC name) of D-psicofuranose in the form of a pentagonal ring is different. was confirmed (FIG. 4). That is, it was confirmed that the following Chemical Formula 3 corresponds to the major, and Chemical Formula 4 corresponds to the minor form.
[99]
[Formula 3]
[100]

[101]
[Formula 4]
[102]

[103]
In addition, D2 is a hydroxy group at carbon 2 (C2) of allulose in a structural isomer relationship with Formula 2 above, and is a glycoside of a hydroxy group at any one of carbons 1 to 6 (C1 to C6) of one molecule of allulose. It was confirmed that they are novel allulose disaccharides that are glycosidic bonds.
[104]
[105]
Example 3: Evaluation of allulose disaccharide acid resistance
[106]
D1 1% (in 10mM citrate buffer) solution was prepared and acid resistance was measured. As controls, sucrose, a disaccharide having a similar structure, and D2, a different allulose disaccharide, were used.
[107]
Using citric acid and sodium citrate 10mM buffer, solutions adjusted to pH 2.0, 4.0 and 6.0 were prepared and stored at room temperature (about 40 degrees), respectively, and the substances remaining after 0 hours, 24 hours, 72 hours and 120 hours The purity of was confirmed through HPLC analysis (HPX-87C column, 80 degrees, 60min, 20ul). The residual ratios of D1, D2 and sucrose are shown in Table 3 below. The concentration of each substance is 1 (%, w/v), and the reaction temperature is 40.
[108]
If there was a statistically significant difference under the same conditions, different alphabets were used.
[109]
[110]
[Table 3]
pH 2, temperature 40 ℃
time (hr) D1 D2 Sucrose p
0 100.0 100.0 100.0 -
24 85.9 A 71.1 C 81.2 B 0.000
72 58.2 A 39.5 C 51.9 B 0.000
120 44.6 A 21.2 C 34.4 B 0.000
pH 4, temperature 40 ℃
time (hr) D1 D2 Sucrose p
0 100.0 100.0 100.0 -
24 99.0 A 98.4 A 98.1 A 0.109
72 98.8 A 95.9 B 95.8 B 0.001
120 97.9 A 93.2 B 92.9 B 0.000
pH 6, temperature 40 ℃
time (hr) D1 D2 Sucrose p
0 100.0 100.0 100.0 -
24 100.0 100.0 100.0 0.781
72 100.0 100.0 99.9 0.397
120 99.96 A* 99.64 A* 99.58 A* 0.069*
[111]
※ Different character strings A, B, and C indicate significant differences between the horizontal row results.
[112]
※ * indicates p<0.1, meaning that D1 and D2 are significant compared to sucrose
[113]
Results according to the measured storage period were analyzed using ANOVA as a statistical analysis and tukey's multiple range test as a post hoc test, and statistical significance was set to p<0.05.
[114]
As a result of the confirmation, the longer the time and the lower the pH, the greater the difference in the residual ratio. In particular, it was confirmed that the residual ratio of D1 after 120 hours at pH 2, which is a strong acidic condition, was about 130% higher than that of sucrose.
[115]
Based on the above results, it was confirmed that D1 has excellent acid resistance compared to D2 and sucrose having a similar structure at pH 6 or less, indicating that acid resistance may be different even for disaccharides having a similar structure, and the novel invention of the present application This indicates that allulose disaccharide has excellent acid resistance.
[116]
From the above description, those skilled in the art to which the present application pertains will understand that the present application may be embodied in other specific forms without changing the technical spirit or essential characteristics thereof. In this regard, it should be understood that the embodiments described above are illustrative in all respects and not restrictive. The scope of the present application should be construed as including all changes or modifications derived from the meaning and scope of the claims to be described later rather than the above detailed description and equivalent concepts thereof.
[117]

WE CLAIM

[Claim 1]Two molecules of allulose are linked by a glycosidic bond, and the glycosidic bond is one molecule of allulose with a different hydroxyl group at carbon 2 (C2) of one molecule of allulose among the two molecules of allulose. 6 (C1 to C6) a compound that is a glycosidic bond (glycosidic bond) to the hydroxyl group of any one carbon of the carbon.
[Claim 2]
The compound of claim 1 , wherein one of the two molecules of allulose is cyclic allulose.
[Claim 3]
The compound according to claim 1, wherein the bond is a glycosidic bond between a hydroxyl group on carbon 2 (C2) of one molecule of cyclic allulose and a hydroxyl group on carbon 6 of another molecule of allulose.
[Claim 4]
The compound according to claim 1, wherein one molecule of the two molecules of allulose is in the form of psicofuranose, and the other molecule is in the form of psicopyranose.
[Claim 5]
2. The compound of claim 1, wherein the compound is 2-(hydroxymethyl)-2-((3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetra Hydro-2H-pyran-3,4,5-triol(2-(hydroxymethyl)-2-((3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetrahydro-2H- pyran-3,4,5-triol).
[Claim 6]
According to claim 1, wherein the compound is represented by the following formula (1), the compound: [Formula 1]
[Claim 7]
2. The compound of claim 1, wherein the compound is (2S,3R,4R,5R)-2-(hydroxymethyl)-2-(((2R,3S,4R,5S)-3,4,5-trihydroxy -5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol ((2S,3R,4R,5R)-2-(hydroxymethyl) -2-(((2R,3S,4R,5S)-3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol) or (2S,3R,4R,5R)-2-(hydroxymethyl)-2-(((2R,3S,4R,5R)-3,4,5-trihydroxy-5-(hydroxymethyl) Tetrahydrofuran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol ((2S,3R,4R,5R)-2-(hydroxymethyl)-2-(((2R, 3S,4R,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triol).
[Claim 8]
According to claim 1, wherein the compound is represented by Formula 3 or Formula 4, the compound: [Formula 3] [Formula 4]
[Claim 9]
The compound according to claim 1, wherein the compound has acid resistance at pH 0.1-7.
[Claim 10]
A saccharide composition comprising the compound of claim 1 and the monosaccharide allulose.
[Claim 11]
A composition for adding food, comprising the compound of claim 1 .