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Flattened Cone 2,8,14,20‐Tetrakis( L ‐valinamido)[4]resorcinarene: An Enantioselective Allosteric Receptor in the Gas Phase
Author(s) -
Botta Bruno,
Caporuscio Fabiana,
Subissati Deborah,
Tafi Andrea,
Botta Maurizio,
Filippi Antonello,
Speranza Maurizio
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200503987
Subject(s) - resorcinarene , enantiomer , chemistry , enantioselective synthesis , derivative (finance) , calixarene , stereochemistry , organic chemistry , molecule , catalysis , financial economics , economics
A get‐out clause : Displacement of the enantiomers of tryptophan from the achiral hydrophobic rim of a flattened cone resorcinarene derivative is induced by 2‐aminobutane ( B ). The displacement exhibits a marked enantioselectivity which 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.