The relatioship between decomposition of amino acid chloramines and their structures

   


1. Russian State Medical University
2. Research Institute of Physical-Chemical Medicine
Type: Experimental/clinical study
UDK: 61:577.112.34      PubMed Id: 20000128
Year: 2009 vol: 55  issue:4  pages: 510-518
Abstract: Rate constants of the decomposition of monoamine α-amino acid chloramine derivatives were determined by a spectrophotometeric method. Several amino acid chloramines with elevated stability have been found. These included n-chloroglycine, n-chlorovaline, n-chlorothreonine, and n-chloroisoleucine. Their molecular structures are characterized by some characteristic feature at the β-position. In the case of glycine chloramine, carbon atom at this position is absent, and the chloramine derivatives of three other amino acids possess branched chains. Partial atomic charges of the electrostatic potential (Wang-Ford) for chloramines of α-amino acids were computed using the semiempirical quantum-mechanical method AM1. The chloramines with elevated stability have high positive sums of charges of three carbon atoms that are atoms at α- and β-positions and a carboxyl group atom. High partial charge also was obtained for one carbon atom at the β-position. These computational values may be employed for prediction of the stability of designed amino acid chloramines. One of the important predictions is that the highest atomic charges and stabilities are characteristics of the amino acid chloramines, in which all hydrogen atoms at the β-position are replaced by carbon-hydrogen chains or hydroxyl groups.
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Reference: Roshchupkin D.I., Murina M.A., Petrova A.O., Sergiyenko V.I., The relatioship between decomposition of amino acid chloramines and their structures, Biomeditsinskaya khimiya, 2009, vol: 55(4), 510-518.
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