Dynamics of Spontaneous Peptidization of l-, d- and dl-Serine in an Abiotic Solution as Investigated with Use of TLC-Densitometry and the Auxiliary Chromatographic Techniques

J Chromatogr Sci. 2016 Aug;54(7):1090-5. doi: 10.1093/chromsci/bmw036. Epub 2016 Mar 14.

Abstract

From our earlier investigations, it comes out that proteinogenic amino acids can undergo spontaneous oscillatory reactions of chiral inversion and peptidization. l-Serine (l-Ser) is an important proteinogenic amino acid with many vital functions in human and mammalian organisms, e.g., it is responsible for good condition of the nervous cell membranes. It undergoes spontaneous oscillatory processes of chiral inversion and peptidization, and the goal of this study was to compare the dynamics of its peptidization with that of d-Ser and dl-Ser (racemate). The main analytical technique used in our experiment was TLC-densitometry, and the auxiliary chromatographic techniques were HPLC-evaporative light scattering detector and LC-MS. The results obtained witness to the differences in peptidization dynamics of the two Ser enantiomers (l and d) and of the racemic mixture thereof (dl). It was shown that dl-Ser characterizes with the higher, and l- and d-Ser with the lower peptidization yields.

MeSH terms

  • Chromatography, Liquid
  • Chromatography, Thin Layer / methods
  • Colloids
  • Densitometry
  • Kinetics
  • Mass Spectrometry
  • Phase Transition*
  • Serine / chemistry*
  • Solutions
  • Stereoisomerism

Substances

  • Colloids
  • Solutions
  • Serine