CHIRALITY ALTERATION OF RACEMIC THIAHETEROHELICENES WITH A LABILE HELIX INCORPORATED INTO ALKYL BETA-D-PYRANOSIDE MICELLES

Alcoholic (5HM) and carboxylic (5HA) derivatives of racemic [5]thiahet erohelicene with a labile helical structure were incorporated into alk yl beta-D-glucoside and -maltoside micelles to exhibit induced CD (ICD ) attributable to the displacement of the equilibrium between helicene -micelle complexes to an (M) enantiomer side. The temperature-dependen ce of the equilibrium constants obtained from the ICD intensities affo rded the thermodynamic parameters, the discrimination energy by the mi celles between the enantiomers being ca. 1.6 kJ mol(-1) for 5HM and ca . 2.5 kJ mol(-1) for 5HA.