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Cellooligosaccharides are the reaction intermediates produced during the hydrolysis of cellulose to glucose. Hence, they have the same chemical structure as cellulose, just shorter chain lengths. Cellooligosaccharides up to DP eight are soluble in water. The soluble cellooligosaccharides can be used "as is" in the food industry as non-digestible oligosaccharides and in the laboratory as representative substrates for cellulolytic enzymes. The soluble cellooligosaccharides may also be chemically modified for use in the laboratory, in this case serving as affinity ligands, reporter groups, or model substrates. A number of methods are available for the separation of cellooligosaccharides differing only with respect to DP. This type of separation is relevant to both laboratory and industrial applications. A new approach to the chromatographic separation of cellooligosacchandes is presented in this thesis. It is shown that cellulose stationary phases, in conjunction with ethanol-water mobile phases, may be used for cellooligosaccharide fractionation. The system appears to behave as an affinity/partition system, with retention times increasing as the DP of the cellooligosaccharides increase. The feasibility of using such a chromatographic system for the "clean-up" of cellooligosaccharide mixtures is demonstrated. The relative merit of different chromatographic approaches putatively used for the fractionation of cellooligosaccharides was determined. Affinity-, adsorption-, ion-mediated- and molecular exclusion-approaches were tested. Adsorption chromatography, using a charcoal-celite stationary phase, was the most generally applicable method for the preparation of near gram quantities of pure cellooligosaccharides. Cellulose-based affinity/partition chromatography was found to be the least time consuming and most economical method for the preparation of cellotetraose and cellopentaose. Studies using chemically modified cellooligosaccharides are typically limited to derivatives whose aglycone group is conjugated to the reducing end of the sugar. This is because the chemistry involved in modifying the reducing end is typically much easier than that involved in selectively modifying other sites on the oligosaccharides. A portion of the studies presented herein was aimed at exploring approaches for the modification of the non-reducing end of cellooligosaccharides. Methyl 6-O-p-nitrobenzoyl-β-D-glucoside was synthesized by reacting methyl 4,6-O-p-nitrobenzylidine-β-Dglucoside with N-bromosuccinimide. This method has potential as a general method for the modification of the reducing terminus of oligosaccharides, including, cellooligosaccharides. / Graduation date: 2003

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Note:

Linear oligosacchardies of 1,4 linked β-D-glucopyranose are commonly referred to as cellodextrins (CD) or cellooligosaccharides (CO). They are of interest to those working in disciplines involving cellulose chemistry because they are often used as model substrates for cellulose itself. They are of interest to food scientists and nutritionists because they are easily incorporated into foods as non-digestible oligosaccharides, a category of food ingredients that is thought to be beneficial lo human health. The intent of the research presented in this thesis was to evaluate the potential of using cellulose supports for the chromatographic separation of soluble CDs differing in their degree of polymerization (DP; a numerical value indicating the number of glucose substituents per molecule). Soluble CDs range in DP from 2 to 8. Thin layer chromatography (TLC), using cellulose-coated TLC plates, was used as a model chromatographic system. Mixed CD preparations, containing CDs ranging in DP from 2 to 8 were prepared by incomplete acid-catalyzed hydrolysis of cellulose. The DP profiles of the different CD preparations were qualitatively demonstrated by TLC using silica-coated plates, an organic solvent-based mobile phase, and a standard carbohydrate visualizing reagent (p-anisaldehye in sulfuric acid). CD-preparations were then chromatographed on cellulose-coated TLC plates. Visualization of the chromatographed CDs was accomplished using a silver nitrate-sodium hydroxide reagent system, a reducing-sugar visualizing reagent. The silver nitrate-sodium hydroxide system was found to be the most appropriate, based on detection limits, simplicity and safety, of the several visualization reagents tested. Eight different mobile phases, all aqueous-based, were tested as potential solvents for the resolution of CDs, differing in DP, on cellulose-coated tlc plates at room temperature. The optimum solvent was found to be 60% ethanol/40% water. This solvent clearly resolved CDs of DP 3, 4 and 5. CD preparations chromatographed with the same mobile phase, but with silica-coated TLC plates, were not resolved. These combined results suggest that the TLC system with the cellulose stationary phase behaves similar to an affinity system, since silica and cellulose are both relatively hydrophilic stationary phases (i.e. both systems are typically considered examples of normal phase adsorption chromatography). The results further illustrate that cellulose supports have potential for use in the preparation of CDs of defined DP. / Graduation date: 2002

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