Conformational Solvation Studies of LIGNOLs with Molecular Dynamics and Conductor-Like Screening Model

Thomas Sandberg,Patrik Eklund,Matti Hotokka

doi:10.3390/ijms13089845

Thomas Sandberg, Patrik Eklund + Show 1 more

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https://doi.org/10.3390/ijms13089845

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Abstract

Molecular dynamics (MD) simulations were performed on sterically hindered α-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.

Highlights

The forest industries are developing new innovative products in addition to the traditional bulk products
The anticarcinogenic and antioxidative lignan hydroxymatairesinol (HMR) is found in large amounts in the knots of Norway spruce (Picea abies) [1]. It has been used in the synthesis of TADDOL-like α-conidendrin-based chiral 1,4-diols (LIGNOLs) [2] with the same functionality as TADDOLs [3,4] or BINOLs [5], which are often used as ligands for transition metal catalysed asymmetric synthesis
The structures of the LIGNOLs included in this study have been quantum chemically optimized [2], and in this study molecular dynamics (MD) simulations are used to explore the conformational changes of the LIGNOLs in aqueous solution

Summary

Introduction

The forest industries are developing new innovative products in addition to the traditional bulk products. The anticarcinogenic and antioxidative lignan hydroxymatairesinol (HMR) is found in large amounts in the knots of Norway spruce (Picea abies) [1] It has been used in the synthesis of TADDOL-like α-conidendrin-based chiral 1,4-diols (LIGNOLs) [2] with the same functionality as TADDOLs [3,4] or BINOLs [5], which are often used as ligands for transition metal catalysed asymmetric synthesis. The structures of the LIGNOLs included in this study have been quantum chemically optimized [2], and in this study MD simulations are used to explore the conformational changes of the LIGNOLs in aqueous solution. Such an analysis has to the best of our knowledge not been performed before

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