The interaction of carbohydrates and amino acids with aromatic systems studied by density functional and semi-empirical molecular orbital calculations with dispersion corrections

Raman Sharma, Jonathan P. McNamara, Rajesh K. Raju, Mark A. Vincent, Ian H. Hillier, Claudio A. Morgado

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

Density functional theory (DFT-D) and semi-empirical (PM3-D) methods having an added dispersion correction have been used to study stabilising carbohydrate-aromatic and amino acid-aromatic interactions. The interaction energy for three simple sugars in different conformations with benzene, all give interaction energies close to 5 kcal mol-1. Our original parameterization of PM3 (PM3-D) seriously overestimates this value, and has prompted a reparametrization which includes a modified core-core interaction term. With two additional parameters, the carbohydrate complexes, as well as the S22 data set, are well reproduced. The new PM3 scheme (PM3-D*) is found to describe the peptide bond-aromatic ring interactions accurately and, together with the DFT-D method, it is used to investigate the interaction of six amino acids with pyrene. Whilst the peptide backbone can adopt both stacked and T-shaped structures in the complexes with similar interaction energies, there is a preference for the unsaturated ring to adopt a stacked structure. Thus, peptides in which the latter interactions are maximised are likely to be the most effective for the functionalisation of carbon nanotubes.

Original languageEnglish
Pages (from-to)2767-2774
Number of pages8
JournalPhysical Chemistry Chemical Physics
Volume10
Issue number19
DOIs
Publication statusPublished - 2008
Externally publishedYes

Fingerprint

Orbital calculations
Aromatic Amino Acids
carbohydrates
Molecular orbitals
amino acids
molecular orbitals
Carbohydrates
Amino Acids
Discrete Fourier transforms
Peptides
acids
Carbon Nanotubes
interactions
Parameterization
Benzene
peptides
Sugars
Density functional theory
Conformations
rings

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Atomic and Molecular Physics, and Optics

Cite this

The interaction of carbohydrates and amino acids with aromatic systems studied by density functional and semi-empirical molecular orbital calculations with dispersion corrections. / Sharma, Raman; McNamara, Jonathan P.; Raju, Rajesh K.; Vincent, Mark A.; Hillier, Ian H.; Morgado, Claudio A.

In: Physical Chemistry Chemical Physics, Vol. 10, No. 19, 2008, p. 2767-2774.

Research output: Contribution to journalArticle

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