Electronic properties of amino acid side chains: quantum mechanics calculation of substituent effects

BACKGROUND Electronic properties of amino acid side chains such as inductive and field effects have not been characterized in any detail. Quantum mechanics (QM) calculations and fundamental equations that account for substituent effects may provide insight into these important properties. PM3 analysis of electron distribution and polarizability was used to derive quantitative scales that describe steric factors, inductive effects, resonance effects, and field effects of amino acid side chains. RESULTS These studies revealed that: (1) different semiempirical QM methods yield similar results for the electronic effects of side chain groups, (2) polarizability, which reflects molecular deformability, represents steric factors in electronic terms, and (3) inductive effects contribute to the propensity of an amino acid for alpha-helices. CONCLUSION The data provide initial characterization of the substituent effects of amino acid side chains and suggest that these properties affect electron density along the peptide backbone.

• Publication year

  2005

• Venue

  BMC Chemical Biology

• Publication date

  2005-08-03

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1186/1472-6769-5-2PMID 16078995PMCID 1185526
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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