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Conformational Solvation Studies of LIGNOLs with Molecular Dynamics and Conductor-Like Screening Model
Centre of Excellence for Functional Materials, Physical Chemistry, Åbo Akademi University, Porthansgatan 3–5, 20500 Åbo (Turku), Finland
Organic Chemistry, Åbo Akademi University, Biskopsgatan 8, 20500 Åbo (Turku), Finland
* Author to whom correspondence should be addressed.
Received: 18 June 2012; in revised form: 16 July 2012 / Accepted: 30 July 2012 / Published: 7 August 2012
Abstract: Molecular dynamics (MD) simulations were performed on sterically hindered -conidendrin-based chiral 1,4-diols (LIGNOLs) from the naturally occurring lignan hydroxymatairesinol (HMR) using the GROMACS software. The aim of this study was to explore the conformational behaviour of the LIGNOLs in aqueous solution adopting the TIP4P model. The topologies of the LIGNOLs were constructed manually and they were modeled with the OPLS-AA force field implemented in GROMACS. The four most relevant torsional angles in the LIGNOLs were properly analyzed during the simulations. The determining property for the conformation preferred in aqueous solution was found to be the lowest energy in gas phase. The solvation effects on the LIGNOLs were also studied by quantum chemical calculations applying the COnductor-like Screening MOdel (COSMO). The hydration studies of the MD simulations showed that several of these LIGNOLs, produced from a renewable source, have a great potential of acting as chiral catalysts.
Keywords: conformation; chiral 1,4-diol; lignan; LIGNOL; molecular dynamics; GROMACS; COSMO
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Sandberg, T.; Eklund, P.; Hotokka, M. Conformational Solvation Studies of LIGNOLs with Molecular Dynamics and Conductor-Like Screening Model. Int. J. Mol. Sci. 2012, 13, 9845-9863.
Sandberg T, Eklund P, Hotokka M. Conformational Solvation Studies of LIGNOLs with Molecular Dynamics and Conductor-Like Screening Model. International Journal of Molecular Sciences. 2012; 13(8):9845-9863.
Sandberg, Thomas; Eklund, Patrik; Hotokka, Matti. 2012. "Conformational Solvation Studies of LIGNOLs with Molecular Dynamics and Conductor-Like Screening Model." Int. J. Mol. Sci. 13, no. 8: 9845-9863.