Article

Conformational analysis of ochratoxin a by NMR spectroscopy and computational molecular modeling.

NMR Laboratory, Department of Chemistry, University of Crete, 71409 Iraklion, Crete, Greece.
The Journal of Physical Chemistry B (impact factor: 3.7). 10/2005; 109(35):16926-36. DOI:10.1021/jp058035e pp.16926-36
Source: PubMed

ABSTRACT Two-dimensional NMR spectroscopy has been used for a complete assignment of the proton and carbon-13 spectra of the metabolite from Aspergillus ochraceus, ochratoxin A. In addition, phase-sensitive nuclear Overhauser effect spectrometry experiments and computational molecular modeling (MM2 and MMFF force field programs) have been employed to examine the conformational properties of ochratoxin A in chloroform solutions. Particular attention has been given to intramolecular hydrogen-bonding formation involving the phenolic group on dihydroisocoumarin, which may be responsible for the toxic mechanism of ochratoxin A.

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Keywords

Aspergillus ochraceus
 
carbon-13 spectra
 
complete assignment
 
computational molecular modeling
 
conformational properties
 
dihydroisocoumarin
 
intramolecular hydrogen-bonding formation
 
metabolite
 
MMFF force field programs
 
ochratoxin
 
ochratoxin A
 
Particular attention
 
phase-sensitive nuclear Overhauser effect spectrometry experiments
 
proton
 
toxic mechanism
 
Two-dimensional NMR spectroscopy