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Title: Gas-phase enantioselectivity of chiral amido[4]resorcinarene receptors
Authors: Botta, B
Caporuscio, F
D'Acquarica, I
Delle Monache, G
Subissati, D
Tafi, Andrea 
Botta, Maurizio 
Filippi, A
Speranza, M.
Issue Date: 2006
Project: None 
Diastereomeric protonbound [1(L)HA](+) complexes between selected amino acids (A=phenylglycine (Phg), tryptophan (Trp), tyrosine methyl ester (TyrOMe), threonine (Thr), and allothreonine (AThr)) and a chiral amido[4]resorcinarene receptor (1(L)) display a significant enantioselectivity when undergoing loss of the amino acid guest A by way of the enantiomers of 2-aminobutanes (B) in the gas phase. The enantioselectivity of the B-to-A displacement is ascribed to a combination of thermodynamic and kinetic factors related to the structure and the stability of the diastereomeric [1(L)HA](+) complexes and of the reaction transition states. The results of the present and previous studies allow classification of the [1(L)HA](+) complexes in three main categories wherein: i) guest A does not present any additional functionalities besides the amino acid one (alanine (Ala), Phg, and phenylalanine (Phe)); ii) guest A presents an additional alcohol function (serine (Ser), Thr, and AThr); and iii) guest A contains several additional functionalities on its aromatic ring (tyrosine (Tyr), TyrOMe, Trp, and 3,4-dihydroxyphenylalanine (DOPA)). Each category exhibits a specific enantioselectivity depending upon the predominant [1(L)HA](+) structures and the orientation of the 2-aminobutane reactant in the relevant adducts observed. The results may contribute to the understanding of the exceptional selectivity and catalytic properties of enzyme mimics towards unsolvated biomolecules.
ISSN: 0947-6539
DOI: 10.1002/chem.200600102
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