[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[O:13]=[CH:14][C@@H:15]([C@H:17]([C@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[OH:18])[OH:16].OCC([C@H]([C@H]([C@@H](CO)O)O)O)=O.O>[Ca]>[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[OH:13][CH2:14][C:15]([C@H:17]([C@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[OH:18])=[O:16]A test chromatographic column of 316 stainless steel and having an inside diameter of 10 mm and a length of 250 mm was prepared for liquid chromatography (LC) for use in establishing the elution profile for d-glucose, d-galactose, and d-tagatose for each stationary phase agent tested. One chromatographic column was filled with about 15.2 gm of DOWEX MONOSPHERE 99Ca/320 (Available from The Dow Chemical Company, Midland, Mich.), a strong acid cation exchange resin in calcium form (or strong acid calcium exchange resin) as stationary phase. Another test column was filled with about 16.3 gm of Mitsubishi DIAION UBK 555 (Available from Mitsubishi Chemical Corporation, Tokyo, Japan) a strong acid exchange resin in calcium form. The DOWEX resin particles were in the form of beads and were nominally 300-330 microns in diameter, and the DIAION particles were nominally 190-240 microns in diameter. Separate 5 wt-% solutions of d-glucose, 5 wt-% d-galactose, and 5 wt-% d-tagatose in deionized water were prepared to inject separately into each chromatography column. The injection volume was about 250 ul. A flow of mobile phase desorbent as deionized water at a rate of 0.5 ml/min was established in the column at a temperature of 65° C. The column was maintained at a temperature of 65° C. Each of the solutions was injected into the column and the eluent from the chromatographic column was monitored by refractive index using a Waters 410 RI detector (Available from Waters Corporation, Milford Mass.). The compositions were analyzed by HPLC. The relative selectivities for each of the sugar species over the DOWEX 99 Ca/320 and the DIAION UBK 555 resins were calculated and are shown hereinbelow in Table 1A. The relative selectivity was determined by considering the retention times for each of the components and the void marker time of the column.
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