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Spontaneous oscillatory in vitro chiral conversion of simple carboxylic acids and its possible mechanism
Author(s) -
Sajewicz Mieczysław,
Matlengiewicz Marek,
Leda Marcin,
Gontarska Monika,
Kronenbach Dorota,
Kowalska Teresa,
Epstein Irving R.
Publication year - 2010
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1739
Subject(s) - chemistry , biuret test , carboxylic acid , context (archaeology) , organic chemistry , mechanism (biology) , condensation reaction , amino acid , aqueous solution , computational chemistry , combinatorial chemistry , catalysis , biochemistry , paleontology , philosophy , epistemology , urea , biology
In earlier studies, we have collected experimental evidence (mostly from thin‐layer chromatography and polarimetry) on the spontaneous oscillatory in vitro chiral conversion of simple carboxylic acids dissolved in 70% aqueous ethanol. To elucidate this phenomenon, we developed a simple theoretical model of two linked Templators. Recently, we have obtained additional experimental evidence of the spontaneous condensation of chiral carboxylic acids, based on the biuret test (amino acids), high performance liquid chromatography, and 13 C NMR spectroscopy (profens and hydroxy acids). We briefly describe our experimental results in the context of the existing literature and outline an improved theoretical model for these phenomena. Our system resembles in some respects the reported oscillatory condensation of organic silanols. Here, the key reaction is the formation of carboxylic acid‐derived enols. Finally, we discuss the importance of the oscillatory chiral conversion of simple carboxylic acids for biochemistry, pharmacology, and related life sciences. Copyright © 2010 John Wiley & Sons, Ltd.