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; Hinterding, Klaus; Brinkmann, Volker; Guerini, Danilo; Müller-Hartwieg, Constanze; Knecht, Helmut; Simeon, Corinne; Streiff, Markus; Wagner, Trixie; Welzenbach, Karl; Zécri, Frédéric; Zollinger, Markus; Cooke, Nigel; Francotte, Eric; Journal of medicinal chemistry 48 (2005) 5373–5377; doi:10.1021/jm050242f

data_1506352
_publ_section_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.
;
_journal_issue                   16
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              5373
_journal_page_last               5377
_journal_paper_doi               10.1021/jm050242f
_journal_volume                  48
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H38 N O6 P'
_chemical_formula_sum            'C28 H38 N O6 P'
_chemical_formula_weight         515.56
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.02(2)
_cell_angle_beta                 86.30(2)
_cell_angle_gamma                76.29(2)
_cell_formula_units_Z            2
_cell_length_a                   6.413(5)
_cell_length_b                   13.141(9)
_cell_length_c                   17.092(9)
_cell_measurement_reflns_used    5603
_cell_measurement_temperature    263(2)
_cell_measurement_theta_max      59.221
_cell_measurement_theta_min      2.625
_cell_volume                     1385.1(16)
_computing_cell_refinement       'Saint V7.03A (Bruker AXS, 2004)'
_computing_data_collection       'SMART V5.630 (Bruker AXS, 2003)'
_computing_data_reduction        'Saint V7.03A (Bruker AXS, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      263(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_sigmaI/netI    0.0930
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25797
_diffrn_reflns_theta_full        65.08
_diffrn_reflns_theta_max         65.08
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_T_max  0.9417
_exptl_absorpt_correction_T_min  0.7044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         8403
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0781
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+1.9465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.2142
_reflns_number_gt                6274
_reflns_number_total             8403
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm050242fsi20050316_082009.cif
_cod_data_source_block           RAL01a
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1506352