Individual stereoisomers of phosphinic dipeptide inhibitor of leucine aminopeptidase |
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Authors: | Mucha Artur Lämmerhofer Michael Lindner Wolfgang Pawełczak Małgorzata Kafarski Paweł |
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Institution: | 1. Department of Bioorganic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland;2. Christian Doppler Laboratory for Molecular Recognition Materials, Department of Analytical Chemistry & Food Chemistry, University of Vienna, Währinger Strasse 38, A-1090 Vienna, Austria;3. Institute of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland |
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Abstract: | Individual stereoisomers of the phosphinic pseudodipeptide hPhepsiP(O)(OH)CH(2)]Phe were obtained by stereoselective liquid chromatographic separation as N- and C-terminally protected derivative on quinidine carbamate modified silica stationary phase. The stereoisomeric purity, exceeding 95% for each fraction, was determined before and after deprotection using two independent methods. The absolute configuration was rationally assigned by application of enantiomerically pure phosphinic acid substrates in the synthetic procedure and correlation with biological activity of the products. Substantial differences in inhibition of leucine aminopeptidase by the individual isomers revealed novel insights into potency of the recently developed and remarkably effective compound. |
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