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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Albert, R. et al.

Albert, Hinterding, Brinkmann, Guerini, Müller-Hartwieg, Knecht, Simeon, Streiff, Wagner, Welzenbach, Zécri, Zollinger, Cooke, Francotte,

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.

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.[1]

References

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, 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. J. Med. Chem. (2005) [Pubmed]

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