Effect of Water Isotopic Composition on Galactose Mutarotation Kinetics

A number of new glycoprotein-based and chiral drugs possessing complex carbohydrate structures have been developed as a result of advances in organic synthesis. Specific features of glycosylation related to carbohydrate tautomerism can play an important role in determining the mechanism of action, pharmacokinetics, pharmacodynamics, stability, and immunogenicity of these drugs. Active discussion in the literature concerning the need for separating the active tautomer and its inert or even toxic optical counterpart stimulates the search for new quality control methods in the production of optically active drugs. Herein, we present results of an investigation of the kinetics of D- and L-galactose mutarotation in aqueous solutions with variable mole fractions of a heavy hydrogen isotope (D/H ratio). © 2015, Springer Science+Business Media New York.