Glucosyl sucrose, production

The treatment of sucrose with anhydrous HF89 results in the formation of a complex mixture of pseudooligo- and poly-saccharides up to dp 14, which were detected by fast-atom-bombardment mass spectrometry (FABMS). Some of the smaller products were isolated and identified by comparison with the known compounds prepared86 88 a-D-Fru/-1,2 2,1 -p-D-Fru/j (1), either free or variously glucosylated, was a major product, and this is in accord with the known stability of the compound. The mechanism of formation of the products in the case of sucrose involves preliminary condensation of two fructose residues. The resultant dianhydride is then glucosylated by glucopyranosyl cation.89 The characterization of this type of compound was an important step because it has permitted an increased understanding of the chemical nature of caramels. 

Thermal activation of sucrose and inulin in the presence of citric acid,93 and sucrose in the presence of acetic94 acid, yields caramels containing, among other products, di-D-fructose dianhydrides and glycosylated difructose dianhydrides, as described in Section V.6). Similarly, the thermal treatment of 6-0-ot-D-glu-copyranosyl-D-fructofuranose (palatinose) in the presence of citric acid87 has been shown to produce appreciable proportions of glucosylated di-D-fructose dianhydrides. 

Various strains of oral streptococci produce D-glucosyltransferases which utilize sucrose as a o-glucosyl donor in the production of soluble and insoluble D-glucans. Consequently, it may be expected that some deoxyfluoro derivatives of sucrose function as competitive inhibitors for the dextransu-crases of tooth bacteria, thus preventing decay, or at least may be used as active-site probes for the enzymes. Another aim of these researches is to find non-metabolizable sweeteners. 

The pathogenesis of dental caries may involve three distinct processes (1) adherence of the bacteria to the tooth, (2) formation of glycocalyx due to synthesis of a sticky glucan by the action of the bacterial enzyme glucosyl transferase on sucrose, and (3) accumulation of biobUm (plaque), within which there is continuing acid production by constituent bacteria (including streptococci and lactobacflli) able to metabolize carbohydrates at low pH values. This acid demineralizes an enamel. 

Strain NRRL B-512(F) produces large proportions of the extracellular enzyme dextransucrase,339 which is responsible for the synthesis of linear sequences ofa-D-(l —> 6)-linked D-glucosyl residues. The enzyme transfers the D-glucosyl group from a sucrose molecule to an enlarging dextran chain and liberates the D-fructose portion. As dextransucrase is an extracellular enzyme, production of dextran by cell-free, culture filtrates can result in enhanced yield and quality, and ease of purification of the product. By suitable adjustment of the conditions, products in a chosen molecular-weight range can be obtained. Formation of branches is not yet well understood, but the enzymes responsible will certainly be found. 

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