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ANANBIOANAL - 2010
Pharmaceutical R & D Summit
doi:10.4172/2155-9872.1000081
Structure Elucidation of Bioactive Compounds by Means of
Circular Dichroism Spectroscopy
Jadwiga Frelek
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka, Warszawa, Poland
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t is well known that the biological properties of bioactive compounds are closely
related to their stereostructure as well as their physicochemical and chemical
properties. Thus, the development of practical methods allowing for the unequivocal
and reliable determination of the absolute configuration is actively researched. The
high level of interest in this subject is, not withstanding the other reasons, related to
the fact that the enantiomers of a particular bio-active compound may demonstrate
differences of up to several orders of magnitude in their pharmaceutical effects
and potency at the same receptor. The fact that one of the enantiomers is usually
more active than its counterpart, which may even be toxic, necessitates the need
to use enantiomerically pure products to avoid adverse effects. In this context,
the chiroptical methods and the circular dichroism (CD) spectroscopy specifically,
appear to be sensitive, fast, and convenient methods for the stereochemical
assignment provided that the compounds studied are chiral and non-racemic.
During the present lecture, the most recent results on the application of electronic
circular dichroism spectroscopy in the structure elucidation of a broad variety of
important bioactive compounds will be presented. The scope of the present lecture
includes, among others, b-lactam antibiotics, amino acids, amino alcohols, vitamins,
and carbohydrates. For the representative derivatives, the CD spectra computed
applying the time-dependent density functional theory (TDDFT) will be compared
to the experimental CD curves. The high sensitivity of the CD spectroscopy to the
minor structural changes will be demonstrated.
ANALBIOANAL-2010
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