Constructing a useful tool for characterizing amino acid conformers by means of quantum chemical and graph theory indices

Constanza Cárdenas, Mateo Obregón, Eugenio-José Llanos, Eduardo Machado, Hugo-Javier Bohórquez, Jose-Luis Villaveces, Manuel-Elkin Patarroyo

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

The aim of this work is to construct a tool to assist in the prediction of peptidic properties resulting from the exchange of two amino acids in a proteic chain. In the past others have used experimental properties for this purpose. However, the nature of these data sets severely limits their access to important properties pertaining to secondary structure, and hence the indices used cannot characterize different backbone conformers like α helix and β strands, or side-chain conformations like gauche+, gauche− and trans. In this study we explore the importance of backbone and side-chain angles with regard to conformer similarity measured with theoretical properties calculated in an ab initio manner. For each of the 20 genetically encoded amino acids, we studied five conformers that correspond to α helical and β strand structures, with three different side chain conformations for each, defined solely by their angles Φ, Ψ and χ1. This methodology allowed each of the 108 conformers to be represented by a mathematical object without ambiguity. The peptidic chain was emulated using two capping models to simulate the effect of nearest neighbors. These are OHCXaaNH2 and AlaXaaAla, where Xaa is the conformer of interest. We then calculated 40 ab initio quantum chemical and graph theory indices for each backbone-side-chain conformer to obtain a characterization and classification scheme. We found that: (1) while backbone structure is very important to conformer similarity, side-chain conformations do not cluster together in a top-level manner; (2) amino acids with π electrons group together independent of backbone conformation.
Original languageEnglish
Pages (from-to)667-682
Number of pages16
JournalComputers & Chemistry
Issue number6
Publication statusPublished - 7 Nov 2002

Keywords / Materials (for Non-textual outputs)

  • Molecular similarity
  • Secondary structure
  • Backbone conformers
  • Side chain conformers
  • Theoretically derived indices
  • Correlation between amino acid conformers


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