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Issue 41, 2006
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Hydration profiles of aromatic amino acids: conformations and vibrations of l-phenylalanine–(H2O)n clusters

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Abstract

IR-UV double resonance spectroscopy and ab initio calculations were employed to investigate the structures and vibrations of the aromatic amino acid, L-phenylalanine–(H2O)n clusters formed in a supersonic free jet. Our results indicate that up to three water molecules are preferentially bound to both the carbonyl oxygen and the carboxyl hydrogen of L-phenylalanine (L-Phe) in a bridged hydrogen-bonded conformation. As the number of water molecules is increased, the bridge becomes longer. Two isomers are found for L-Phe–(H2O)1, and both of them form a cyclic hydrogen-bond between the carboxyl group and the water molecule. In L-Phe–(H2O)2, only one isomer was identified, in which two water molecules form extended cyclic hydrogen bonds with the carboxyl group. In the calculated structure of L-Phe–(H2O)3 the bridge of water molecules becomes larger and exhibits an extended hydrogen-bond to the π-system. Finally, in isolated L-Phe, the D conformer was found to be the most stable conformer by the experiment and by the ab initio calculation.

Graphical abstract: Hydration profiles of aromatic amino acids: conformations and vibrations of l-phenylalanine–(H2O)n clusters

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Article information


Submitted
29 Jun 2006
Accepted
04 Sep 2006
First published
14 Sep 2006

Phys. Chem. Chem. Phys., 2006,8, 4783-4791
Article type
Paper

Hydration profiles of aromatic amino acids: conformations and vibrations of L-phenylalanine–(H2O)n clusters

T. Ebata, T. Hashimoto, T. Ito, Y. Inokuchi, F. Altunsu, B. Brutschy and P. Tarakeshwar, Phys. Chem. Chem. Phys., 2006, 8, 4783
DOI: 10.1039/B609229B

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