Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/5165
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dc.contributor.authorBotta, Ben_us
dc.contributor.authorCaporuscio, Fen_us
dc.contributor.authorD'Acquarica, Ien_us
dc.contributor.authorDelle Monache, Gen_us
dc.contributor.authorSubissati, Den_us
dc.contributor.authorTafi, Andreaen_us
dc.contributor.authorBotta, Maurizioen_us
dc.contributor.authorFilippi, Aen_us
dc.contributor.authorSperanza, M.en_us
dc.date.accessioned2021-03-30T15:49:33Z-
dc.date.available2021-03-30T15:49:33Z-
dc.date.issued2006-
dc.identifier.issn0947-6539en_US
dc.identifier.urihttp://hdl.handle.net/20.500.12779/5165-
dc.description36159en_US
dc.description.abstractDiastereomeric 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.en_US
dc.language.isoenen_US
dc.relationNoneen_US
dc.relation.ispartofCHEMISTRY-A EUROPEAN JOURNALen_US
dc.titleGas-phase enantioselectivity of chiral amido[4]resorcinarene receptorsen_US
dc.typeArticleen_US
dc.identifier.doi10.1002/chem.200600102en_US
dc.identifier.pmid16881028en_US
dc.identifier.scopus2-s2.0-33750569096en_US
dc.identifier.isiWOS:000241913600016en_US
dc.relation.volume12en_US
dc.relation.issue31en_US
dc.description.firstpage8096en_US
dc.description.lastpage8105en_US
dc.description.thirdmissionNot applicableen_US
item.cerifentitytypePublications-
item.grantfulltextnone-
item.languageiso639-1en-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.openairetypeArticle-
item.fulltextNo Fulltext-
crisitem.author.orcid0000-0003-4308-3531-
crisitem.author.orcid0000-0003-0456-6995-
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