83
Chapter 5
α-Amino Acids In Water: A Review
Of VCD And Roa Spectra
Jan Cz. Dobrowolski, Piotr F.J. Lipiński, Joanna E. Rode and Joanna Sadlej
J. C. dobrowolski () · J. E. Rode
Industrial Chemistry Research Institute, 8 Rydygiera Street, 01-793, Warsaw, Poland
e-mail: j.dobrowolski@nil.gov.pl
P. J. F. Lipiński
mossakowski medical Research Centre
Polish Academy of Sciences
5 Pawinskiego Street, 02-106 Warsaw, Poland
J. C. dobrowolski · J. Sadlej
National Medicines Institute, 30/34 Chełmska Street, 00-725, Warsaw, Poland
J. Sadlej
Faculty of Chemistry, university of Warsaw, 1 Pasteura Street, 02-093, Warsaw, Poland
Abstract An up-to-date perspective on the capability of vibrational Circular dichroism (vCd) and Raman optical Activity (RoA) spectroscopy of the 20 encoded
α-amino acids to solve the structural problems appearing in water is provided in this
review. VCD and ROA spectroscopy of the α-amino acid molecules reviewed in
this chapter refer only to free and single amino acids in water at various ph levels.
to well understand the implications of such studies for biology and medicine, we
devote one subchapter to the role of free amino acids in an organism’s metabolism
and physiology. A variety of side chains that modify the α-amino acids character
from acidic to basic and from hydrophilic to hydrophobic makes the possible dissociation equilibria in water very complex and dependent on several factors. therefore, information on dissociation constants, isoelectric points, and hydrophobicity
parameters of α-amino acids is summarised in the next subchapter. The conformational variety, complexity of interactions, and entanglement of equilibria makes
considering the influence of these factors on vCd and RoA spectra with quantum
chemical analysis absolutely necessary. the elements of the theory of chiroptical
vibrational spectra and methods enabling solvent simulations are provided in the
subsequent subchapter. We report on experimental methods, techniques and tricks
for measuring and simulating the vCd and RoA spectra in water at different ph
levels. the review is concluded by listing the not-yet-measured amino acids, a presentation of the main challenges for computational methods, and suggestions for the
most promising experimental techniques that may be used in future studies.
Keywords Amino acids • Vibrational circular dichroism • Raman optical activity •
Water • Experimental • Theoretical • Ab initio • DFT • Quantum mechanical calculation
m. Baranska (ed.), Optical Spectroscopy and Computational Methods in Biology and
Medicine, Challenges and Advances in Computational Chemistry and Physics 14,
doI 10.1007/978-94-007-7832-0_5, © Springer Science+Business media dordrecht 2014
Chapter 5
α-Amino Acids In Water: A Review
Of VCD And Roa Spectra
Jan Cz. Dobrowolski, Piotr F.J. Lipiński, Joanna E. Rode and Joanna Sadlej
J. C. dobrowolski () · J. E. Rode
Industrial Chemistry Research Institute, 8 Rydygiera Street, 01-793, Warsaw, Poland
e-mail: j.dobrowolski@nil.gov.pl
P. J. F. Lipiński
mossakowski medical Research Centre
Polish Academy of Sciences
5 Pawinskiego Street, 02-106 Warsaw, Poland
J. C. dobrowolski · J. Sadlej
National Medicines Institute, 30/34 Chełmska Street, 00-725, Warsaw, Poland
J. Sadlej
Faculty of Chemistry, university of Warsaw, 1 Pasteura Street, 02-093, Warsaw, Poland
Abstract An up-to-date perspective on the capability of vibrational Circular dichroism (vCd) and Raman optical Activity (RoA) spectroscopy of the 20 encoded
α-amino acids to solve the structural problems appearing in water is provided in this
review. VCD and ROA spectroscopy of the α-amino acid molecules reviewed in
this chapter refer only to free and single amino acids in water at various ph levels.
to well understand the implications of such studies for biology and medicine, we
devote one subchapter to the role of free amino acids in an organism’s metabolism
and physiology. A variety of side chains that modify the α-amino acids character
from acidic to basic and from hydrophilic to hydrophobic makes the possible dissociation equilibria in water very complex and dependent on several factors. therefore, information on dissociation constants, isoelectric points, and hydrophobicity
parameters of α-amino acids is summarised in the next subchapter. The conformational variety, complexity of interactions, and entanglement of equilibria makes
considering the influence of these factors on vCd and RoA spectra with quantum
chemical analysis absolutely necessary. the elements of the theory of chiroptical
vibrational spectra and methods enabling solvent simulations are provided in the
subsequent subchapter. We report on experimental methods, techniques and tricks
for measuring and simulating the vCd and RoA spectra in water at different ph
levels. the review is concluded by listing the not-yet-measured amino acids, a presentation of the main challenges for computational methods, and suggestions for the
most promising experimental techniques that may be used in future studies.
Keywords Amino acids • Vibrational circular dichroism • Raman optical activity •
Water • Experimental • Theoretical • Ab initio • DFT • Quantum mechanical calculation
m. Baranska (ed.), Optical Spectroscopy and Computational Methods in Biology and
Medicine, Challenges and Advances in Computational Chemistry and Physics 14,
doI 10.1007/978-94-007-7832-0_5, © Springer Science+Business media dordrecht 2014