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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.

Albert, Rainer and Hinterding, Klaus and Brinkmann, Volker and Guerini, Danilo and Mueller-Hartwieg, Constanze and Knecht, Helmut and Simeon, Corina and Streiff, Markus and Wagner, Beatrix and Welzenbach, Karl and Zecri, Frederic and Zollinger, Markus and 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

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