<br/>For some time, it has been known that the reaction of glucose with diammonium phosphate (DAP) and other salts of ammonia yields depending on the pH of the solution a mixture of deoxyfructosazine [(1r,2s,3r)-1-{5-[(2s,3r)-2,3,4-trihydroxybutyl]pyrazin-2-yl}butane-1,2,3,4-tetrol] and fructoazine [1,2,3,4-Butanetetrol, 1,1'-(2,5-pyrazinediyl)bis-, (1R-(1R*,1'*,2S*,2'S*,3R,3R*))] among many other compounds ranging from pyrazines to intensely colored polymeric materials, which upon pyrolysis breakdown to various <i>heterocyclic</i> nitrogen compounds. When such reactions are carried out industrially, such as the production of certain reconstituted tobaccos, other sugars are present such as maltose and sucrose. It has been known since the work of Jezo in 1963, that sucrose must be hydrolyzed to glucose and fructose before it will react with ammonia and its compounds. However, it appears that the reactions of maltose with DAP and similar ammonium salts have not been reported in the literature. In the research to be presented, the reactions of glucose and maltose with DAP in aqueous solution at 80 C for 2 h were studied. Both glucose and maltose gave highly colored solutions although the final solution from maltose had a reddish-brown color while the final solution from glucose was dark brown. Based on the analogy with glucose, reaction of maltose should give a deoxyfructoazine-like molecule with glucose units linked to each of the four-carbon side chains. Previous attempts at finding such species failed when an ion-exchange type column was used to separate the reaction mixture. In the current work, a Cogent Amide column (250 x 4.6 mm) with ≈85/15 CH3CN/H2O at 2 mL/min as the mobile phase with both RI and UV detection at 195 and 280 nm was used. Column temperature was 45 C. Deoxyfructosazine was tentatively identified in the reaction of glucose with DAP. Retenton time was longer than that for sucrose. Thus, finding the reaction product of maltose and DAP was unlikely under the current set of chromatographic conditions and a less polar column will be used for the next set of experiments. Based on the chromatographic results, it appeared that most of the glucose and the maltose had been consumed by the reaction with DAP.

New look at reactions between maltose and other reducing disaccharides and ammonium salts

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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