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- Title
Computational ECD Spectrum Simulation of the Phytotoxin Scytalone: Importance of Solvent Effects on Conformer Populations.
- Authors
Mazzeo, Giuseppe; Cimmino, Alessio; Andolfi, Anna; Evidente, Antonio; Superchi, Stefano
- Abstract
ABSTRACT A time-dependent Density Functional Theory (TDDFT) computational simulation of the electronic circular dichroism (ECD) spectrum of the phytotoxin scytalone ( 1), produced by different plant pathogenic fungi and involved in melanin production, was undertaken with the aim to establish a nonempirical correlation between the spectrum and the absolute configuration of this compound. In fact, very low optical rotation data of 1 do not afford a reliable absolute configuration assignment while, on the contrary, the use of ECD can provide a useful tool for its stereochemical description. This structurally simple molecule displayed a considerable molecular flexibility, which made it mandatory to obtain an accurate conformers distribution to get a good reproduction of the experimental ECD spectrum. Only the application of an implicit integral equation formalism Polarizable Continuum Model (IEF-PCM) solvation model in the calculations allowed us to properly describe the conformer populations and finally obtain a more than satisfactory spectral simulation. Chirality 26:142-148, 2014. © 2014 Wiley Periodicals, Inc.
- Subjects
PHYTOTOXINS; CONFORMERS (Chemistry); TIME-dependent density functional theory; CIRCULAR dichroism; INTEGRAL equations; ORGANIC solvents
- Publication
Chirality, 2014, Vol 26, Issue 9, p142
- ISSN
0899-0042
- Publication type
Article
- DOI
10.1002/chir.22311