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Theoretical study of the NLO responses of some natural and unnatural amino acids used as probe molecules

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Abstract

The first hyperpolarizabilities β of the natural aromatic amino acids tryptophan and tyrosine have been investigated using several methods and basis sets. Some of the theoretical results obtained were compared to the only experimental hyper-Rayleigh scattering data available. The sensitivity of tryptophan to its local environment was analyzed by constructing two-dimensional potential energy plots around the dipeptide tryptophan-lysine. Static hyperpolarizabilities β(0) of the found minima were calculated by a second-order Møller–Plesset (MP2) method in combination with the 6-31 + G(d) basis set. Moreover, the efficiency of tryptophan and those of a series of unnatural amino acids as endogenous probe molecules were tested by calculating the nonlinear responses of some peptides. Impressive results were obtained for the amino acid ALADAN, which shows significantly improved nonlinear performance compared to other amino acids with weak nonlinear responses.

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Acknowledgments

The author M S-R thanks the Alexander von Humboldt-Stiftung, Bonn for financial support.

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Authors and Affiliations

  1. Laboratoire de Microscopie, Microanalyse de la matière et Spectroscopie Moléculaire, Université Djilali Liabès, B.P 89, Sidi Bel Abbès, 22000, Algérie

    S. N. Derrar & M. Sekkal-Rahal

  2. Laboratoire de Biochimie Théorique, UPR9080 CNRS, Institut de Biologie Physico-Chimique, 13 Rue Pierre et Marie Curie, 75005, Paris, France

    P. Derreumaux

  3. Institut Universitaire de France, 103 Bvd Saint Michel, 75005, Paris, France

    P. Derreumaux

  4. Physikalische und Theoretische Chemie, Universitaet des Saarlandes, Postfach 15 11 50, Saarbruecken, 66041, Germany

    M. Springborg

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  1. S. N. Derrar
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  2. M. Sekkal-Rahal
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  3. P. Derreumaux
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Correspondence to M. Sekkal-Rahal.

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Derrar, S.N., Sekkal-Rahal, M., Derreumaux, P. et al. Theoretical study of the NLO responses of some natural and unnatural amino acids used as probe molecules. J Mol Model 20, 2388 (2014). https://doi.org/10.1007/s00894-014-2388-0

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  • DOI: https://doi.org/10.1007/s00894-014-2388-0

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