Complexation of Al(III) by aromatic amino acids in the gas phase.
The coordination properties of three natural aromatic amino acids (AAAs)-phenylalanine (Phe), tyrosine (Tyr), and tryptophan (Trp)-to AlIII are studied in this work, devoting special attention to the role of the aromatic side chain. A comparison with aluminum(III)-alanine complexes is also presented. The polarizability arising from the ring has been seen to be a key factor in the stability of the complexes, with the order being Trp-AlIII > Tyr-AlIII > Phe-AlIII, starting from the most stable one. Cation-pi interactions between the metal and the aromatic ring are present in the lowest energy conformers, especially for Trp, which seems to be very well suited for these kinds of interactions, occurring with both the six- and five-membered rings of the indole side chain. The most stable coordination mode for the three AAAs is found to be tricoordinated with the N and O of the backbone chain and the aromatic ring, as was found theoretically and experimentally for other metals.
Rezabal
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Kimika Fakultatea, Euskal Herriko Unibertsitatea and Donostia International Physics Center, PK 1072, 20080 Donostia, Euskadi, Spain. pobrease@sc.ehu.es
Marino
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T
Mercero
J M
JM
Russo
N
N
Ugalde
J M
JM
D000409:Alanine / Q000737:chemistry; D000535:Aluminum / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002412:Cations; D008670:Metals / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D010649:Phenylalanine / Q000737:chemistry*; D012984:Software; D012997:Solvents / Q000737:chemistry; D014364:Tryptophan / Q000737:chemistry*; D014443:Tyrosine / Q000737:chemistry*
D000596:Amino Acids; D002412:Cations; D008670:Metals; D012997:Solvents; D014443:Tyrosine; D010649:Phenylalanine; D014364:Tryptophan; D000535:Aluminum; D009584:Nitrogen; D000409:Alanine; D010100:Oxygen