Abstract
Kinetic data have been determined for the acid-catalyzed hydrolysis of the xylosidic bond in 2- O-(4- O-methyl-α- D-glucopyranosyluronic acid)xylobiose, 2′- O-(4- O-methyl-α- D-glucopyranosyluronic acid)xylobiose, and 2′ O-(4- O-methyl-α- D-glucopyranosyl)xylobiose. Xylobiose is hydrolyzed 1.2, 7.0, and 3.4 times as fast as the above compounds, respectively, indicating the stabilizing effect of the 4- O-methyl- D-glucuronic acid residue. The lower rate of hydrolysis of the xylosidic bond in the trisaccharides is attributed to conformational and steric effects. There is no evidence for the existence of any “activating inductive effect”, postulated by earlier investigators.
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