SYNTHESIS OF 5-THIOMANNOSE-CONTAINING OLIGOMANNOSIDE MIMICS - BINDINGABILITIES TO CONCANAVALIN-A

5-Thiomannose-containing oligomannoside mimics, 5SMan alpha(1,6)Man, 5 SMan alpha(1,3)Man, 5SMan alpha(1,6){Man alpha(1,3)Man}, Man alpha(1,6 ){5SMan alpha(1,3)Man}, and 5SMan alpha(1,6){5SMan alpha(1,3)Man}, wer e synthesized. Dissociation constants for the binding of these mimics to concanavalin A (ConA) were determined by a fluorescence anisotropy inhibition assay. Comparison of these data with those of the natural o ligomannosides and with a crystal structure of the trimannoside-ConA c omplex established that replacing a ring oxygen atom with a sulfur ato m causes about 1 kcal/mol decrease in the binding free energy when the ring oxygen is recognized with a hydrogen bonding. (C) 1998 Elsevier Science Ltd. All rights reserved.