Enzymes in organic chemistry. Part 10: Chemo-enzymatic synthesis of l-phosphaserine and l-phosphaisoserine and enantioseparation of amino-hydroxyethylphosphonic acids by non-aqueous capillary electrophoresis with quinine carbamate as chiral ion pair agent |
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| Institution: | 1. Institut für Organische Chemie der Universität Wien, Währingerstraße 38, A-1090 Wien, Austria;2. Institut für Analytische Chemie der Universität Wien, Währingerstraße 38, A-1090 Wien, Austria;1. Dipartimento di Farmacia, Università di Pisa, Via Bonanno 6, 56126 Pisa, Italy;2. CNR Istituto di Fisiologia Clinica, Via Moruzzi, 1, 56124 Pisa, Italy;3. ANSTO LifeSciences, PO Box M34, Camperdown 2050, Australia;4. Fondazione Toscana G. Monasterio, Via Moruzzi, 1, 56124 Pisa, Italy;1. Department of Mathematics and Natural Sciences, School of Arts and Sciences, American University of Ras Al Khaimah, Ras Al Khaimah, United Arab Emirates;2. Medicinal and Process Chemistry Division, Sector 10, Jankipuram Extension, Sitapur Road, CSIR-Central Drug Research Institute, Lucknow, 226 031, UP, India |
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| Abstract: | Diisopropyl 2-azido-1-acetoxyethylphosphonate (±)-7 was hydrolysed with high enantioselectivity by lipase SP 524 to give α-hydroxyphosphonate (S)-(−)-6 and ester (R)-(−)-7, which was saponified to give (R)-(+)-6. The two α-hydroxyphosphonates (R)- and (S)-6 were transformed into l-phosphaisoserine and l-phosphaserine, respectively. Their enantiomeric excesses were determined to be 97% by HPLC on an chiral stationary phase. A mixture of all four stereoisomeric amino-hydroxyethylphosphonic acids can be separated by non-aqueous capillary electrophoresis with quinine carbamate as the chiral ion pair agent applying the partial filling technique. |
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