Title of Invention: Composition for preparing allulose and method for preparing allulose using the same
technical field
[One]
The present application relates to a composition for preparing allulose and a method of using the same.
[2]
background
[3]
In order to stably store and distribute saccharides, research has been conducted on the development (utilization) of precursors for the production of saccharides. As an example, International Patent Publication No. WO2012-113405 A1 discloses a precursor composition for preparing a component of human milk oligosaccharide with high purity, which is difficult to synthesize or purify by a chemical or enzymatic method. However, there is no research on a precursor composition for preparing allulose, a material that has recently been spotlighted as a low-calorie saccharide.
[4]
DETAILED DESCRIPTION OF THE INVENTION
technical challenge
[5]
Under this background, the present inventors have completed the present application by confirming that the novel compound can be used as a precursor for the production of allulose.
[6]
means of solving the problem
[7]
The present application provides a novel composition for preparing allulose, and a method for preparing allulose using the same.
[8]
Effects of the Invention
[9]
The allulose precursor of the present application can be conveniently converted into allulose, and since the level of conversion to other substances other than allulose is low, it can be usefully used to improve the quality stability of a food composition containing allulose.
[10]
Brief description of the drawing
[11]
1 is an HPLC chromatogram analyzed by a size exclusion column (Biorad Aminex HPX-87C) of disaccharides generated during the preparation of allulose.
[12]
FIG. 2 is an HPLC chromatogram of D1 and D2 analyzed by a normal phase column (YMC Pack Polyamine II) of a mixture of disaccharides generated during the preparation of allulose using a size exclusion column.
[13]
3 shows the three-dimensional structure of D1, which is an allulose disaccharide.
[14]
4 shows the structure and carbon numbering of allulose.
[15]
Best mode for carrying out the invention
[16]
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.
[17]
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 embodiments of the present application described herein. Also, such equivalents are intended to be covered by this application.
[18]
[19]
One aspect of the present application provides a novel allulose precursor.
[20]
The allulose precursor of the present application may include an allulose disaccharide. The allulose precursor of the present application may have a structure of allulose disaccharide.
[21]
"Allulose disaccharide" in the present application means "a compound in which two molecules of allulose are linked by a glycosidic bond". The term "allulose disaccharide" may also be referred to as "allulose dimer", "allulose diploid", "disaccharide allulose".
[22]
Specifically, in the allulose disaccharide, two molecules of allulose are linked by a glycosidic bond, and the glycosidic bond is allulose having a different hydroxyl group on carbon 2 (C2) of one molecule of allulose among the two molecules of allulose. Loss 1 to 6 (C1 to C6) carbons of 1 molecule may be a glycosidic bond to the hydroxyl group of any one carbon.
[23]
Specifically, at least one molecule of two molecules of allulose is cyclic allulose, and a hydroxyl group at carbon 2 of the cyclic allulose and a hydroxyl group at any one carbon of carbon 1 to 6 of another allulose molecule It may be a compound connected between them by a glycosidic bond. The number of glycosidic bonds may be 1 to 2, specifically, 1 may be.
[24]
In one embodiment, it may be a glycosidic bond between a hydroxyl group on carbon 2 of the cyclic allulose and a hydroxyl group on carbon 6 of another allulose.
[25]
In one embodiment, in the allulose precursor, 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. In one embodiment, the allulose precursor may be a compound represented by the following formula (1).
[26]
[Formula 1]
[27]

[28]
In one embodiment, the allulose precursor of the present application is 2-(hydroxymethyl)-2-((3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl) Methoxy)tetrahydro-2H-pyran-3,4,5-triol (2-(hydroxymethyl)-2-((3,4,5-trihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)methoxy) It may be a compound named 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.
[29]
(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-psico furanose) or 6-O-β-D-Psycopyranosyl-β-D-Psicopyranosyl -β-D-psico furanose) may be collectively named.
[30]
(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 (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-tri All((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-tri All((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.
[31]
Specifically, the compound of Formula 1 may exist in two forms of Formulas 2 and/or 3 below.
[32]
[Formula 2]
[33]

[34]
[Formula 3]
[35]

[36]
The compound of Formula 2 is 6-O-β-D-Psycopyranosyl-α-D-Psycofuranose (6-O-β-D-Psicopyranosyl-α-D-psicofuranose), and the compound of Formula 3 is 6 -O-β-D-Psycopyranosyl-β-D-Psycofuranose (6-O-β-D-Psicopyranosyl-β-D-psicofuranose).
[37]
The allulose precursor of the present application may be converted into allulose by heating.
[38]
The heating may be performed at a temperature of 60°C or higher and 100°C or lower, and more specifically, it may be performed at a temperature of 60°C or higher and 95°C or lower, 65°C or higher 95°C or lower, 70°C or higher and 95°C or lower. It is not limited thereto.
[39]
The heating may be performed for more than 0 hours and 108 hours or less, specifically, 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours. , 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, or may be carried out for more than 12 hours, but is not limited thereto.
[40]
When the allulose precursor of the present application is converted to allulose, 20 parts by weight or more may be converted to allulose based on 100 parts by weight of the initial allulose precursor. Specifically, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 90, 95, or 99 parts by weight or more may be converted based on 100 parts by weight of the initial allulose precursor, Or 100 parts by weight, that is, all of the allulose precursor may be converted to allulose, but is not limited thereto.
[41]
Meanwhile, the conversion may be performed for more than 0 hours and not more than 108 hours, specifically, 10 minutes, 20 minutes, 30 minutes, 40 minutes, 50 minutes, 1 hour, 2 hours, 3 hours, 4 hours, 5 hours. hours, 6 hours, 7 hours, 8 hours, 9 hours, 10 hours, 11 hours, or 12 hours or more, but is not limited thereto.
[42]
When the allulose precursor of the present application is converted to allulose, the amount of by-products generated other than the desired allulose may be 10 parts by weight or less based on 100 parts by weight of the total composition. Specifically, it may be 10, 9, 8, 7.5, 7, 6.5, 6, 5.5, 5, 4.5, 4, 3.5, 3, 2.5, 2, 1.5, or 1 part by weight or less. Alternatively, 0 parts by weight based on 100 parts by weight of the total composition, that is, by-products may not be generated, but is not limited thereto.
[43]
[44]
Another aspect of the present application provides the use of an allulose disaccharide as an allulose precursor.
[45]
Another aspect of the present application provides an allulose precursor composition comprising an allulose disaccharide.
[46]
Another aspect of the present application provides the use of an allulose disaccharide for use in the preparation of allulose.
[47]
Another aspect of the present application provides a composition for preparing allulose including allulose disaccharide.
[48]
Another aspect of the present application provides a method for producing allulose comprising heating allulose disaccharide.
[49]
[50]
As described above, since the allulose disaccharide of the present application can be converted to allulose, the allulose disaccharide can be applied to the production of allulose. Allulose disaccharides, precursors and heating are as described above.
[51]
Another aspect of the present application provides a method for producing allulose, comprising heating a composition comprising allulose disaccharide.
[52]
As described above, since the allulose disaccharide of the present application can be converted to allulose, a composition including the allulose disaccharide can be applied to the production of allulose. Allulose disaccharide, precursor, and heating are as described above.
[53]
Heating the allulose disaccharide may be that allulose disaccharide is converted to allulose or that allulose is produced, but is not limited thereto
[54]
[55]
The composition may include saccharides. Specifically, it may further include allulose. However, it is not limited thereto.
[56]
[57]
The content of allulose disaccharide in the composition including allulose disaccharide may be greater than 0 and 15 parts by weight or less of allulose disaccharide relative to 100 parts by weight of the total saccharides contained in the composition. Specifically, it may contain allulose disaccharides in an amount of more than 0.0001 parts by weight, more than 0.001 parts by weight, more than 0.01 parts by weight, more than 0.1 parts by weight, or more than 0.15 parts by weight and not more than 15 parts by weight, based on 100 parts by weight of the total saccharides, , and/or, 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, allulose disaccharide relative to 100 parts by weight of total saccharides; 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 parts by weight or less, or 1 part by weight or less and may be included in an amount exceeding 0 parts by weight, but is not limited thereto.
[58]
[59]
The composition may be a food composition.
[60]
The food composition is included without limitation as long as it is a food in which allulose can be used. Specifically, it 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, carbonated beverage, fruit juice, fruit and vegetable beverage, dietary fiber beverage, carbonated water, wheat flour, tea, coffee, etc.), alcoholic beverage, bakery, sauce (eg, ketchup, pork cutlet sauce) etc.), dairy products (eg, fermented milk, processed milk, etc.), processed meat products (eg, ham, sausage, jerky, etc.), chocolate products, gum, candy, jelly, ice cream, syrup, dressing, snacks (eg, cookies, crackers, biscuits, etc.) etc.), pickled fruits and vegetables (eg, cheong, dangchim fruit, red ginseng extract or red ginseng slices, etc.), meal substitutes (eg, frozen food, retort food, home meal replacement (HMR), etc.) or processed food. However, this is only an example and is not limited thereto.
[61]
[62]
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, fructose, and allulose, 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, synthetic sweeteners such as sucralose, saccharin, and aspartame may be used.
[63]
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 acidifying agents and salting agents used in carbonated beverages. 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. In addition, a person skilled in the art may appropriately select and add substances that may be normally included in the food composition, and the ratio of these additives may be selected in the range of 0.001 to 1 parts by weight, or 0.01 to 0.20 parts by weight per 100 parts by weight of the food composition of the present application. can, but is not limited thereto.
[64]
[65]
Another aspect of the present application provides a method for enhancing the quality stability of food, comprising heating a food composition comprising allulose disaccharide.
[66]
The food may contain allulose.
[67]
The "improvement of quality stability" means any denaturation that may occur during distribution, storage, and processing, and suppressing deterioration of quality due to this, or lowering the level of denaturation and deterioration that has already occurred. Specifically, the denaturation may include a phenomenon in which allulose is changed to a substance other than allulose, such as crystallization, browning, and oxidation/reduction reaction, or the physical properties thereof are changed.
[68]
When allulose or a composition containing the same is stored for a long period of time, a problem of deterioration of food quality may occur due to denaturation such as crystallization of allulose. However, when the allulose precursor of the present application is added to food, it is heated It can also be used to improve food quality stability by obtaining allulose at a desired time.
[69]
The food is the same as described above.
[70]
Modes for carrying out the invention
[71]
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.
[72]
[73]
Example 1. Isolation of allulose precursors
[74]
In the process of preparing allulose known from US 2018-0327796 A1, a novel substance was isolated through HPLC.
[75]
Specifically, it was confirmed that the desired disaccharide component was generated according to the HPLC chromatogram analysis conditions of Table 1 below, and it was confirmed that a new unknown substance other than allulose was generated from the stock solution as shown in FIG. 1 . Allulose was identified at 21.1 minutes and novel material at 31.7 minutes.
[76]
[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 30℃
[77]
[78]
In order to separate the resulting novel material, it was precisely separated again under the conditions of Table 2 using HPLC and a normal phase column.
[79]
[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℃
[80]
[81]
[82]
As a result, it was confirmed that the material that appeared as one peak under the HPLC conditions of Table 1 appeared as two peaks under the separation conditions of Table 2 (FIG. 2), 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.
[83]
[84]
Further analysis of ESI-MS, 1 H NMR, and 13 C NMR was performed on D1.
[85]
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.
[86]
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.
[87]
[88]
As a result, it was confirmed that D1 is a novel compound in which two molecules of allulose are bonded and has the structure of Formula 1 below.
[89]
[Formula 1]
[90]

[91]
In addition, D1 has two forms, major or minor form (FIG. 3), and 6-O-β-D-Psicopyranosyl-α-D-psicofuranose, which is a major form, is represented by the following Chemical Formula 2, minor form 6-O-β -D-Psicopyranosyl-β-D-psicofuranose was confirmed to have a structure of the following formula (3).
[92]
[Formula 2]
[93]

[94]
[Formula 3]
[95]

[96]
The compound of formula 2 (6-O-β-D-Psicopyranosyl-α-D-psicofuranose) is compound A, and the compound of formula 3 (6-O-β-D-Psicopyranosyl-β-D-psicofuranose) is compound B named as
[97]
In addition, D2 is different from the hydroxyl group of carbon 2 (C2; according to carbon numbering in FIG. 4) of allulose in a structural isomer relationship with the compound of Formula 1, and positions 1 to 6 (C1 to C6) of one molecule of allulose It was confirmed that they were novel allulose disaccharides, which are glycosidic bonds of the hydroxyl group of any one of the carbons.
[98]
In the following experiment, an experiment was performed to confirm that the novel compounds D1 and D2 can be used as allulose precursors.
[99]
[100]
Example 2, Allulose Production Using Allulose Precursors
[101]
Example 2-1: Comparison of heat conversion reaction of allulose disaccharide
[102]
Ultrapure water without impurities was added to the two types of disaccharides, D1 and D2, separated in Example 1 above to prepare a sample having a concentration of 1% (w/w), and used as Experimental Examples 1 and 2, respectively. To compare the decomposition reaction according to heating conditions, sugar (CJ Cheiljedang, purity 99% or more) composed of one molecule of glucose and fructose was selected as the most common disaccharide (dimer). Similarly, ultrapure water was added to 1% (w/w) was prepared as a sample and used as Comparative Example 1.
[103]
Each prepared sample was placed in a sealed glass reagent bottle and heated in a water bath (Water bath, Daehan Science) preheated to 70, 80, 90, and 95°C. The heated sample was collected and sampled at intervals of 12 hours, and the change was analyzed under the conditions of Table 1 using HPLC. All experiments were repeated three times, and the results are shown in Table 3 below.
[104]
[Table 3]
[105]
※ Different character strings A, B, and C mean that there is a significant difference (p<0.05) between Experimental Example 1, Experimental Example 2, and Comparative Example 1 in the horizontal direction
[106]
※ % of monosaccharides and disaccharides refers to the weight ratio (%, w/w) of the total analyzed saccharides, and others are classified as other saccharides.
[107]
[108]
As a result, the conversion rate to monosaccharides at the same level of heat damage (temperature, time) was found to be significantly higher in D1, followed by D2 and sugar in the order of higher conversion rates.
[109]
Specifically, under the highest temperature condition of 95°C, in the case of D1, about 74% of D1 was converted to allulose (monosaccharide) as the target ingredient after 12 hours, and 98% or more was converted after 24 hours, confirming that allulose was produced. On the other hand, D2 was converted to about 58% after 12 hours and 89% after 24 hours, and sugar was confirmed to have relatively insignificant conversion to monosaccharides at 23% and 40% levels, respectively.
[110]
Basically, in both Experimental Examples 1 and 2 and Comparative Example 1, the higher the heating temperature and the longer the heating time, the more the disaccharides are decomposed and converted to monosaccharides. Allulose) was significantly faster and the purity of the converted monosaccharide was maintained high, confirming that the conversion efficiency was high.
[111]
In particular, in the case of D1, it was confirmed that the conversion to allulose was faster and high-purity results were obtained compared with D2, which is an allulose disaccharide.
[112]
[113]
Example 2-2: Utilization of Allulose Precursors in Food Models Containing Allulose
[114]
It was verified by adding D1, a disaccharide, to a food model containing allulose as a main ingredient, whether the conversion to the target ingredient was smooth even in the form present in the mixture rather than the precursor alone.
[115]
Specifically, a beverage model was prepared by dissolving pure allulose crystals with minimal impurities (CJ Cheiljedang, purity of 99.8% or more) and D1 among the previously separated disaccharides in purified water (Experimental Example 3). The prepared Experimental Example 3 was heat-treated for about 1 hour at 95°C, which is one of the usual beverage processing conditions, and whether the disaccharide added in Experimental Example 3 is converted to allulose before and after the heat treatment was determined using HPLC under the conditions of Table 1 was analyzed. The detailed composition ratio of each sample and the change before and after heating are shown in Table 4 below. Likewise, all experiments were repeated three times.
[116]
[117]
[Table 4]
classification Heating time
(95℃) Weight ratio in total solids (%) Total solids
(g/100g)
Monosaccharides
(Allulose) Disaccharides
(D1) Etc
Experimental Example 3 initial value 95.24 4.74 0.02 10.0
after 60 minutes 98.46 1.53 0.01 10.0
[118]
As a result, in the case of Experimental Example 3 in which D1 was added as an allulose precursor to allulose, it was confirmed that D1 was converted into allulose, a desired component, and the purity of allulose was increased. Specifically, in the case of Experimental Example 3, D1 contained in a ratio of about 4.7% of the total solid content was decreased to about 1.5% (-3.2%) after heat treatment, and on the contrary, allulose, the target component, increased to the same amount.
[119]
That is, it was confirmed that D1 is converted into allulose, a target component, under general processing (heating) treatment conditions, and at the same time, it has properties suitable as a precursor by preventing the generation of unintentional products.
[120]
Furthermore, as D1 as a precursor receives thermal energy, a positive effect can be expected that can suppress the denaturation (disappearance) of allulose, which is a useful component, by exposure to excessive thermal damage to some extent.
[121]
[122]
Example 2-3: Comparison of precursor utilization by temperature and solid concentration conditions
[123]
The conversion characteristics of D1 to allulose were tested under various temperature and solid concentration conditions. The isolated precursor D1 was added to the pure allulose monosaccharide in the same manner as in Example 2-2 previously tested, and the concentration of the solid content was adjusted using purified water. Detailed compositions of the prepared Experimental Examples 4 to 6 are shown in Tables 5 and 6 below.
[124]
[125]
First, the conversion rate of D1 was compared when heated for 24 hours under different temperature conditions at 40, 60, and 80 °C (Table 5).
[126]
[127]
[Table 5]
sample classification Heating temperature
(℃) Heating time
(hr) Percentage of total solids (%) Total solids
(g/100g)
Monomer
(Allulose) dimer
(D1)
Experimental Example 4 initial value - - 94.3 2.0 20.0
after heating 40 24 95.1B 1.5A 20.0
60 24 97.6A 0.6B 20.0
80 24 96.5C 0.5C 20.0
[128]
※ Strings ABC that are different in the vertical direction mean that there is a significant difference (p<0.05) compared to the time of manufacture in the same sample
[129]
[130]
As in the previous experiment, it was confirmed that D1 was converted into allulose, the desired component, and the purity of allulose was increased under all temperature conditions. In particular, it was confirmed that most of them were converted to allulose when heated at a temperature of 60 to 80°C.
[131]
[132]
Next, the conversion rate of D1 was compared when heated at high temperature (121° C.) for a short period of time (15 minutes) at different concentrations of solid content of 10 and 30% (w/w, g/100g) (Table 6).
[133]
[134]
[Table 6]
sample classification Total solids
(g/100g) Percentage of total solids (%) Heating temperature
(℃) Heating time
(hr)
Monomer
(Allulose) dimer
(D1)
Experimental Example 5 initial value 10.0 95.2 2.1 - -
after heating 10.0 98.6A 0.5B 121 15
Experimental Example 6 initial value 30.0 95.2 2.1 - -
after heating 30.0 97.3B 0.8A 121 15
[135]
※ Strings ABC that are different in the vertical direction mean that there is a significant difference (p<0.05) compared to the time of manufacture in the same sample
[136]
[137]
As in the previous experiment, it was confirmed that when heat treatment was performed under all concentration conditions, D1 was converted to allulose, a desired component, and the purity of allulose was increased. In particular, it was confirmed that the lower the total solid content, the higher the efficiency of D1 conversion to allulose even after heat treatment.
[138]
[139]
Through this experimental process, it was confirmed that the allulose disaccharide of the present application has high efficiency as a precursor to be converted into allulose, a high value-added material beneficial to consumers.
[140]
In particular, it was confirmed that allulose, the target material of the final step, is generated through a simple heating reaction (normal processing level) rather than a complicated conversion reaction. There is no unintentional generation of impurities and allulose is exposed to excessive heat damage. It was confirmed that it has the potential to preserve it so that it does not occur. Based on this effect, it can be expected to utilize D1 as a precursor that can enhance and preserve the purity of allulose in food and beverage products.
[141]
[142]
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.
Claims
[Claim 1]
A composition for preparing allulose comprising allulose disaccharides.
[Claim 2]
The method according to claim 1, wherein, in the allulose disaccharide, two molecules of allulose are linked by a glycosidic bond, and the glycosidic bond is the second carbon (C2) of one molecule of allulose among the two molecules of allulose. A composition for preparing allulose, wherein the hydroxyl group is bonded to the hydroxyl group of any one carbon of the 1st to 6th (C1 to C6) carbons of one molecule of other allulose.
[Claim 3]
A method for preparing allulose, comprising heating a composition comprising allulose disaccharides.
[Claim 4]
The method according to claim 3, wherein, in the allulose disaccharide, two molecules of allulose are linked by a glycosidic bond, and the glycosidic bond is the second carbon (C2) of one molecule of allulose among the two molecules of allulose. A method for producing allulose, wherein the hydroxyl group is bonded to a hydroxyl group of any one of carbons 1 to 6 (C1 to C6) of one molecule of other allulose.
[Claim 5]
The method according to claim 3, wherein the heating is performed at a temperature of 60°C or higher and 100°C or lower.
[Claim 6]
The method according to claim 3, wherein the composition comprising allulose disaccharide further comprises allulose.
[Claim 7]
The method according to claim 3, wherein the allulose disaccharide contained in the composition is a precursor of allulose.
[Claim 8]
Use of an allulose disaccharide as an allulose precursor.