Research article
Condensation oscillations in the peptidization of phenylglycine
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* Corresponding author: Irving R Epstein epstein@brandeis.edu
1 Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice, Poland
2 Chemistry Department, MS 015, Brandeis University, Waltham, MA 02454-9110, USA
3 Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Journal of Systems Chemistry 2010, 1:7 doi:10.1186/1759-2208-1-7
Published: 18 August 2010Abstract
In earlier studies, we showed that certain low-molecular-weight carboxylic acids (profens, amino acids, hydroxy acids) can undergo spontaneous in vitro chiral conversion accompanied by condensation to from oligomers, and we proposed two simple models to describe these processes. Here, we present the results of investigations using non-chiral high-performance liquid chromatography with diode array detector (HPLC-DAD) and mass spectrometry (MS) on the dynamics of peptidization of S-, R-, and rac-phenylglycine dissolved in 70% aqueous ethanol and stored for times up to one year. The experimental results demonstrate that peptidization of phenylglycine can occur in an oscillatory fashion. We also describe, and carry out simulations with, three models that capture key aspects of the oscillatory condensation and chiral conversion processes.