Novel immunomodulator FTY720 is phosphorylated in rats and humans to form a single stereoisomer. Identification, chemical proof, and biological characterization of the biologically active species and its enantiomer.
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Albert, Rainer, Hinterding, Klaus, Brinkmann, Volker, Guerini, Danilo, Mueller-Hartwieg, Constanze, Knecht, Helmut, Simeon, Corina, Streiff, Markus, Wagner, Beatrix, Welzenbach, Karl, Zecri, Frederic, Zollinger, Markus, Cooke, Nigel Graham and Francotte, Eric (2005) Novel immunomodulator FTY720 is phosphorylated in rats and humans to form a single stereoisomer. Identification, chemical proof, and biological characterization of the biologically active species and its enantiomer. Journal of Medicinal Chemistry, 48 (16). pp. 5373-5377. ISSN 0022-2623
Abstract
In vivo phosphorylation of FTY720 (1) in rats and humans resulted exclusively in the biologically active (S)-configured enantiomer, which was proven by an ex vivo o-phthaldialdehyde derivatization protocol especially elaborated for phosphates of 1. Starting from the prochiral amino alcohol 1, racemic and enantiomerically pure phosphates of 1 were synthesized. Pure enantiomers were obtained after purification of a partially protected key intermediate on an enantioselective support. The absolute stereochemistry was determined by X-ray diffraction.
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| Date Deposited: | 14 Dec 2009 13:58 |
| Last Modified: | 31 Jan 2013 01:14 |
| URI: | https://oak.novartis.com/id/eprint/519 |