Cyclic taurine analogs. Synthesis and effects on ATP-dependent Ca2+ uptake in rat retina.

Syntheses of (+/-)trans- and (+/-)cis-2-aminocyclohexane sulfonic acid (TAHS and CAHS) and (+/-)trans-2-aminocyclopentane sulfonic acid (TAPS) were achieved. In solution, the preferred conformations of TAHS and CAHS have been determined by high field NMR to be diequatorial and equatorial (sulfonic acid moiety)-axial (amino moiety) respectively. When these agents were evaluated as cyclic analogs of taurine in rat retina, TAHS and TAPS inhibited ATP-dependent calcium uptake in the micromolar range, whereas CAHS stimulated calcium uptake in the millimolar range in a manner similar to taurine. TAHS and TAPS are the most potent inhibitors of ATP-dependent calcium uptake in the rat retinal preparation yet reported.