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. 2005 Aug 11;48(16):5373-7.
doi: 10.1021/jm050242f.

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

Rainer Albert  1 , Klaus Hinterding, Volker Brinkmann, Danilo Guerini, Constanze Müller-Hartwieg, Helmut Knecht, Corinne Simeon, Markus Streiff, Trixie Wagner, Karl Welzenbach, Frédéric Zécri, Markus Zollinger, Nigel Cooke, Eric Francotte
Affiliations

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

Rainer Albert et al. J Med Chem. .

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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