N-Benzyl-(1-deoxy-1-
p-toluidino)-D-fructosylamine gives extensive browning on heating in methanol or ethyl acetate especially in the present acid, and from the browned solutions
N-benzyl-D-arabinonamide has been isolated. Under stream of oxygen the browning is less extensive but the yield of D-arabinonamide is increased; under nitrogen the browning is slight and unchanged diaminosugar has been recovered. In the presence of an excess of benzylamine, benzylammonium D-arabinonate has been isolated.
N-Cyclohexyl-(2-cyclohexylamino-2-deoxy)-D-glucosylamine on heating with acid in stream of oxygen gives small amounts of
N,
N-bis (cyclohexyl)-oxaldiamide, dicyclohexyliminoglyoxal and cyclohexylammonium D-arabinonate as the oxidation products. The mechanism of the oxidative cleavages has been explained in terms of the high reducing ability of the enediamine structures which are formed by rearrangement of 1, 2-diaminosugars; in the case of
N-cyclohexyl-(2-cyclohexylamino-2-deoxy)-D-glucosylamine dehydrogenation of the enediamine structure to diiminoglucosone should be involved. The findings are applied to explain the fragmentation of sugar molecules in the amino-carbonyl reactions.
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