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This paper may be viewed at the American Chemical Society's website (http://pubs.acs.org/subscribe/journals/tcaw/10/i11/html/11regs.html)

Summary. All of the eleven tested bi-and tricyclic sugar acetals were found to be competitive inhibitors of glucose exit from human red cells. The highest-affinity agents were those locked into a CI conformation by fusion with a m-dioxane ring attached to a phenyl group (methyl-4,6-O-benzylidene-o-glucopyranoside, K i = 0.73 mM; 4,6-O-benzylidene-o-glucopyranose, /s mM at 23 ~ All of the isopropylidene acetals had less affinity than D-glucose (Sen-Widdas Kin=2.5 raM) for the transport system. Sugars in which two or more hydroxyl groups were cross-linked by isopropylidene groups apparently penetrated the red cell membrane by simple diffusion, as shown by a lack of (1) saturation in the entry process, (2) competition for entry with other acetals or D-glucose, and (3) inhibition by phloretin or Hg 2+ on entry rates.

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