Fluorine-1 9 magnetization transfer studies have been used to measure the transport rate of glucopyranosyl fluorides under equilibrium exchange conditions. Although rate constants and permeabilities could be determined for ,B-D-glucopyranosyl fluoride, the exchange rate for aD -glucopyranosyl fluoride was found to be too slow for determination using this method. The time-dependent decomposition of the ,B-glucopyranosyl fluoride also limits the accuracy of the numerical results for this species; however, it is clear that the permeabilities of the a and P forms differ significantly, i.e., P > P,. This observation is in contrast to recent observations for n-fluoro-n-deoxyglucose, for which P,, > PJ, for n = 2, 3, 4, or 6. The difference can be explained in terms of a simple alternating conformation model in which one of the conformations (with an external sugar-binding site) exhibits a preference for the form of the molecule, while the second conformation (with an internal sugar binding site) exhibits a preference for the a form. Fluorine/hydroxyl substitutions unmask these preferences by selectively reducing the binding to one of the conformations, depending on the specific site of fluorination.