IR/UV spectra and quantum chemical calculations of Trp–Ser: Stacking interactions between backbone and indole side-chain

Thomas Häber; Kai Seefeld; Gernot Engler; Stefan Grimme; Karl Kleinermanns

doi:10.1039/B718710F

IR/UV spectra and quantum chemical calculations of Trp–Ser: Stacking interactions between backbone and indole side-chain

Thomas Häber,^a Kai Seefeld,^a Gernot Engler,^a Stefan Grimme*^b and Karl Kleinermanns*^a

* Corresponding authors

^a Institut für Physikalische Chemie, Heinrich-Heine Universität Düsseldorf, Universitätsstr. 1, Düsseldorf, Germany
E-mail: kleinermanns@uni-duesseldorf.de

^b Theoretische Organische Chemie, Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, Münster, Germany
E-mail: grimmes@uni-muenster.de

Abstract

We present infrared-UV double resonance spectra and quantum chemical calculations of the natural di-peptide H–Trp–Ser–OH. Two conformers are present in the supersonic expansions. They have a compact folded structure with two hydrogen bonds and with the serin residue stacked above the indole ring and an unusual NH(Trp)⋯O [double bond, length as m-dash] C interaction in the lowest energy conformer. Conformational assignments are based on comparison with calculated (B97-D/TZV2P) structures and vibrational frequencies. Inclusion of dispersion in the quantum chemical calculations is mandatory for an accurate description of the conformer energies. We provide comparisons between methods often used in biochemistry and the dispersion-corrected double hybrid functional (B2PLYP-D) as a reference. Only concerted experimental and theoretical studies can unravel the conformational complexity already present in a dipeptide.

This article is part of the themed collection: Stacking interactions

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https://doi.org/10.1039/B718710F

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Paper

Submitted

03 Dec 2007

Accepted

18 Feb 2008

First published

11 Mar 2008

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Phys. Chem. Chem. Phys., 2008,10, 2844-2851

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IR/UV spectra and quantum chemical calculations of Trp–Ser: Stacking interactions between backbone and indole side-chain

T. Häber, K. Seefeld, G. Engler, S. Grimme and K. Kleinermanns, Phys. Chem. Chem. Phys., 2008, 10, 2844 DOI: 10.1039/B718710F

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Physical Chemistry Chemical Physics

IR/UV spectra and quantum chemical calculations of Trp–Ser: Stacking interactions between backbone and indole side-chain

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IR/UV spectra and quantum chemical calculations of Trp–Ser: Stacking interactions between backbone and indole side-chain

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