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Contents Vol 68(3)

Serine and Cysteine π-Interactions in Nature: A Comparison of the Frequency, Structure, and Stability of Contacts Involving Oxygen and Sulfur

Hanzala B. Hussain A , Katie A. Wilson A and Stacey D. Wetmore A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry and Biochemistry, University of Lethbridge, 4401 University Drive W, Lethbridge, Alberta T1K 3M4, Canada.

B Corresponding author. Email: stacey.wetmore@uleth.ca

Australian Journal of Chemistry 68(3) 385-395 https://doi.org/10.1071/CH14598
Submitted: 1 October 2014  Accepted: 3 November 2014   Published: 9 December 2014

Abstract

Despite many DNA–protein π-interactions in high-resolution crystal structures, only four X–H···π or X···π interactions were found between serine (Ser) or cysteine (Cys) and DNA nucleobase π-systems in over 100 DNA–protein complexes (where X = O for Ser and X = S for Cys). Nevertheless, 126 non-covalent contacts occur between Ser or Cys and the aromatic amino acids in many binding arrangements within proteins. Furthermore, Ser and Cys protein–protein π-interactions occur with similar frequencies and strengths. Most importantly, due to the great stability that can be provided to biological macromolecules (up to –20 kJ mol–1 for neutral π-systems or –40 kJ mol–1 for cationic π-systems), Ser and Cys π-interactions should be considered when analyzing protein stability and function.


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