Phenylisoserine in the gas-phase and water: Ab initio studies on neutral and zwitterion conformers.

Journal of Molecular Modeling
Joanna E RodeJoanna Sadlej

Abstract

The conformational landscape of phenylisoserine (PhIS) was studied. Trial structures were generated by allowing for all combinations of single-bond rotamers. Based on the B3LYP/aug-cc-pVDZ calculations 54 conformers were found to be stable in the gas phase. The six most stable conformers were further optimized at the B3LYP/aug-cc-pVTZ and MP2/aug-cc-pVDZ levels for which characteristic intramolecular hydrogen bond types were classified. To estimate the influence of water on PhIS conformation, the IEF-PCM/B3LYP/aug-cc-pVDZ calculations were carried out and showed 51 neutral and six zwitterionic conformers to be stable in water solution. According to DFT calculations, the conformer equilibrium in the gas phase is dominated by one conformer, whereas the MP2 calculations suggest three PhIS structures to be significantly populated. Comparison of DFT and MP2 energies of all 57 structures stable in water indicates that, in practice, one zwitterionic and one neutral conformer determine the equilibrium in water. Based on the AIM calculations, we found that for the neutral conformers in vacuum and in water, d(H...B) is linearly correlated with Laplacian at the H-bond critical point. Figure Phenylisoserine (PhIS) is an active side chain o...Continue Reading

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Citations

Mar 1, 2017·Journal of Molecular Graphics & Modelling·Maciej Janicki, Marek Lozynski
Oct 25, 2014·Chemical Reviews·Shridhar R GadreNityananda Sahu
May 17, 2012·Journal of Chemical Information and Modeling·Michał H JamrózJan Cz Dobrowolski

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Software Mentioned

AIM
Gaussian

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