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Article: Competition between π and Non-π Cation-Binding Sites in Aromatic Amino Acids: A Theoretical Study of Alkali Metal Cation (Li+, Na +, K+)-Phenylalanine Complexes

TitleCompetition between π and Non-π Cation-Binding Sites in Aromatic Amino Acids: A Theoretical Study of Alkali Metal Cation (Li+, Na +, K+)-Phenylalanine Complexes
Authors
KeywordsAlkali Metals
Binding Affinities
Cation-Pi Interactions
Molecular Modeling
Phenylalanine
Issue Date2004
PublisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistry
Citation
Chemistry - A European Journal, 2004, v. 10 n. 8, p. 1966-1976 How to Cite?
AbstractTo understand the cation-π interaction in aromatic amino acids and peptides, the binding of M+ (where M+ = Li+, Na+, and K+) to phenylalanine (Phe) is studied at the best level of density functional theory reported so far. The different modes of M+ binding show the same order of binding affinity (Li+ > Na+ > K+), in the approximate ratio of 2.2:1.5:1.0. The most stable binding mode is one in which the M+ is stabilized by a tridentate interaction between the cation and the carbonyl oxygen (O=C), amino nitrogen (-NH2), and aromatic π ring; the absolute Li+, Na+, and K+ affinities are estimated theoretically to be 275, 201, and 141 kJ mol-1, respectively. Factors affecting the relative stabilities of various M +-Phe binding modes and conformers have been identified, with ion-dipole interaction playing an important role. We found that the trend of π and non-π cation bonding distances (Na+-π > Na +-N > Na+-O and K+ -π > K +-N > K+-O) in our theoretical Na+/K +-Phe structures are in agreement with the reported X-ray crystal structures of model synthetic receptors (sodium and potassium bound lariat ether complexes), even though the average alkali metal cation-π distance found in the crystal structures is longer. This difference between the solid and the gas-phase structures can be reconciled by taking the higher coordination number of the cations in the lariat ether complexes into account.
Persistent Identifierhttp://hdl.handle.net/10722/167946
ISSN
2015 Impact Factor: 5.771
2015 SCImago Journal Rankings: 2.323
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorSiu, FMen_US
dc.contributor.authorMa, NLen_US
dc.contributor.authorTsang, CWen_US
dc.date.accessioned2012-10-08T03:13:14Z-
dc.date.available2012-10-08T03:13:14Z-
dc.date.issued2004en_US
dc.identifier.citationChemistry - A European Journal, 2004, v. 10 n. 8, p. 1966-1976en_US
dc.identifier.issn0947-6539en_US
dc.identifier.urihttp://hdl.handle.net/10722/167946-
dc.description.abstractTo understand the cation-π interaction in aromatic amino acids and peptides, the binding of M+ (where M+ = Li+, Na+, and K+) to phenylalanine (Phe) is studied at the best level of density functional theory reported so far. The different modes of M+ binding show the same order of binding affinity (Li+ > Na+ > K+), in the approximate ratio of 2.2:1.5:1.0. The most stable binding mode is one in which the M+ is stabilized by a tridentate interaction between the cation and the carbonyl oxygen (O=C), amino nitrogen (-NH2), and aromatic π ring; the absolute Li+, Na+, and K+ affinities are estimated theoretically to be 275, 201, and 141 kJ mol-1, respectively. Factors affecting the relative stabilities of various M +-Phe binding modes and conformers have been identified, with ion-dipole interaction playing an important role. We found that the trend of π and non-π cation bonding distances (Na+-π > Na +-N > Na+-O and K+ -π > K +-N > K+-O) in our theoretical Na+/K +-Phe structures are in agreement with the reported X-ray crystal structures of model synthetic receptors (sodium and potassium bound lariat ether complexes), even though the average alkali metal cation-π distance found in the crystal structures is longer. This difference between the solid and the gas-phase structures can be reconciled by taking the higher coordination number of the cations in the lariat ether complexes into account.en_US
dc.languageengen_US
dc.publisherWiley - V C H Verlag GmbH & Co KGaA. The Journal's web site is located at http://www.wiley-vch.de/home/chemistryen_US
dc.relation.ispartofChemistry - A European Journalen_US
dc.subjectAlkali Metalsen_US
dc.subjectBinding Affinitiesen_US
dc.subjectCation-Pi Interactionsen_US
dc.subjectMolecular Modelingen_US
dc.subjectPhenylalanineen_US
dc.titleCompetition between π and Non-π Cation-Binding Sites in Aromatic Amino Acids: A Theoretical Study of Alkali Metal Cation (Li+, Na +, K+)-Phenylalanine Complexesen_US
dc.typeArticleen_US
dc.identifier.emailSiu, FM:fmsiu@hku.hken_US
dc.identifier.authoritySiu, FM=rp00776en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1002/chem.200305519en_US
dc.identifier.pmid15079836-
dc.identifier.scopuseid_2-s2.0-2342420683en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-2342420683&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume10en_US
dc.identifier.issue8en_US
dc.identifier.spage1966en_US
dc.identifier.epage1976en_US
dc.identifier.isiWOS:000221025200012-
dc.publisher.placeGermanyen_US
dc.identifier.scopusauthoridSiu, FM=6701518489en_US
dc.identifier.scopusauthoridMa, NL=7103357185en_US
dc.identifier.scopusauthoridTsang, CW=7202935952en_US

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