Document Report Card

ID: ALA1144403

Journal: J Med Chem

Title: 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.

Authors: Albert R, Hinterding K, Brinkmann V, Guerini D, Müller-Hartwieg C, Knecht H, Simeon C, Streiff M, Wagner T, Welzenbach K, Zécri F, Zollinger M, Cooke N, Francotte E.

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.

CiteXplore: 16078855

DOI: 10.1021/jm050242f