Novel allulose-derived compound
A technique of psicose and compound, which is applied in the field of psicose compositions, can solve the problems that psicose derivatives cannot be separated, and is difficult to identify specific properties, and achieves the effect of high acid resistance
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Embodiment 1
[0059] Example 1: Separation of novel psicose disaccharides
[0060] During the psicose manufacturing process disclosed in Korean Patent No. 10-1723007, in a different manner from that disclosed in International Patent Publication No. WO2018 / 127669, before the psicose crystallization step ) to separate the disaccharides from solution. Specifically, by performing HPLC under the HPLC analysis conditions listed in Table 1 below, it was confirmed that prior to the crystallization step, in addition to psicose, novel (unknown) substances were produced in the solution, such as figure 2 shown.
[0061] Although the amount of the novel substance isolated as described above varied slightly depending on the production method, it was confirmed that the amount of the novel substance contained in the initial solution was 2% or less and increased to about 5% depending on the storage time.
[0062] Table 1
[0063] equipment Agilent technologies 1200 Series column Bio...
Embodiment 2
[0071] Example 2: Identification of psicose disaccharides
[0072] D1 identified in Example 1 was further analyzed.
[0073] The main component, 6-O-β-D-psicopyranosyl-α-D-psicfuranose, is a white amorphous powder, ESI-MS m / z 365[M+Na] + ; 1 H NMR (850MHz,D 2 O)δ H 3.44(1H,d,J=12.0Hz),3.47(1H,d,J=12.0Hz),3.56(1H,dd,J=11.0,5.0Hz),3.60(1H,d,J=12.0Hz), 3.62(1H,dd,J=11.0,2.5Hz),3.70(1H,br d,J=12.5Hz),3.75(1H,d,J=12.0Hz),3.75(1H,br m a ),3.82(1H,brd,J=12.5Hz),3.84(1H,br s),3.92(1H,t,J=3.0Hz),3.97(1H,d,J=5.5Hz),4.09(1H, t,J=5.5Hz), 4.13(1H,br m)[D 2 O signal δ H 4.70]; 13 C NMR signal b δ C 57.6, 60.4, 62.9, 64.7, 64.9, 69.1, 68.9, 70.2, 70.3, 81.2, 101.8, 103.4.
[0074] A. Difficulty measuring spin-spin splitting (multiplicity) and coupling constants due to peak overlap.
[0075] B. By interpreting NMR's HSQC (850MHz, D 2 O) and HMBC (850MHz, D 2 O) Spectral data, obtained 13 C NMR peak information.
[0076] The minor component, 6-O-β-D-psicopyranosyl-β-D-psic...
Embodiment 3
[0088] Example 3: Evaluation of acid resistance of psicose disaccharide
[0089] A 1% D1 solution (in 10 mM citrate buffer) was prepared to measure its acid resistance. Sucrose, which is a disaccharide having a similar structure, and D2, which is another psicose disaccharide, were used as controls.
[0090] The pH of the solution was adjusted to pH 2.0, 4.0 and 6.0 using 10 mM citrate buffer and sodium citrate buffer. The prepared solutions were stored at room temperature (about 40°C), respectively, and the purity of the remaining material was identified by HPLC analysis (HPX-87C column, 80°C, 60min, 20μl) at 0 hours, 24 hours, 72 hours and 120 hours. The residual percentages of D1, D2 and sucrose are shown in Table 3 below. The concentration of each substance was 1% (w / v), and the reaction temperature was 40°C.
[0091] Those results showing statistically significant differences under the same experimental conditions are indicated by different letters.
[0092] table ...
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