The gas-phase 2-aminobutane-induced displacement of the enantiomers of tryptophan from the achiral hydrophobic rim of flattened cone 2,8,14,20-tetrakis(L-valinamido)[4] resorcinarene, exhibits a marked kinetic enantioselectivity. This nantioselectivity is traced to a conformational coupling between the achiral hydrophobic rim of the resorcinarene host and its chiral hydrophilic rim wherein the 2-aminobutane enantiomers are trapped. This type of conformational coupling is therefore regarded as the first example of enantioselective allosteric effect, more specifically, of heterotropic negative cooperativity in the gas phase.
Flattened cone 2,8,14,20-tetrakis(L-valinamido)[4]resorcinarene: An enantioselective allosteric receptor in the gas phase / Botta, Bruno; D., Subissati; A., Tafi; M., Botta; Filippi, Antonello; Caporuscio, Fabiana; Speranza, Maurizio. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - STAMPA. - 45:(2006), pp. 2717-2720. [10.1002/anie.200503987]
Flattened cone 2,8,14,20-tetrakis(L-valinamido)[4]resorcinarene: An enantioselective allosteric receptor in the gas phase
BOTTA, Bruno;FILIPPI, Antonello;CAPORUSCIO, Fabiana;SPERANZA, Maurizio
2006
Abstract
The gas-phase 2-aminobutane-induced displacement of the enantiomers of tryptophan from the achiral hydrophobic rim of flattened cone 2,8,14,20-tetrakis(L-valinamido)[4] resorcinarene, exhibits a marked kinetic enantioselectivity. This nantioselectivity is traced to a conformational coupling between the achiral hydrophobic rim of the resorcinarene host and its chiral hydrophilic rim wherein the 2-aminobutane enantiomers are trapped. This type of conformational coupling is therefore regarded as the first example of enantioselective allosteric effect, more specifically, of heterotropic negative cooperativity in the gas phase.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
