Sanglifehrin-Cyclophilin Interaction: Degradation Work, Synthetic Macrocyclic Analogues, X-ray Crystal Structure, and Binding Data
Richard Sedrani; Jörg Kallen; Luisa M. Martin Cabrejas; Charles D. Papageorgiou; Francesco Senia; Stefan Rohrbach; Dieter Wagner; Binh Thai; Anne-Marie Jutzi Eme; Julien France; Lukas Oberer; Grety Rihs; Gerhard Zenke; Jürgen Wagner; Journal of the American Chemical Society 125 (2003) 3849–3859; doi:10.1021/ja021327y

data_4113591
_publ_contact_author
;
      J\"urgen Wagner
      Novartis Pharma AG
      S-507.312
      CH-4002 Basel
      Schweiz
;
_publ_contact_author_email       juergen.wagner@pharma.novartis.com
_publ_contact_author_fax         '++41 (0)61 3244513'
_publ_contact_author_phone       '++41 (0)61 3242683'
_publ_section_title
;
 Sanglifehrin-Cyclophilin Interaction: Degradation Work, Synthetic
 Macrocyclic Analogues, X-ray Crystal Structure, and Binding Data
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3849
_journal_page_last               3859
_journal_paper_doi               10.1021/ja021327y
_journal_volume                  125
_journal_year                    2003
_chemical_compound_source        'see paper'
_chemical_formula_sum            'C20 H33 N O4 S'
_chemical_formula_weight         383.53
_chemical_name_systematic
; 
(E)-(2R,3R,4S)-1-((R)-10,10-Dimethyl-3,3-dioxo-3-thia-4-aza-
tricyclo[5.2.1]dec-4-yl)-3-hydroxy-2,4-dimethyl-oct-6-en-1-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 101.47(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.095(2)
_cell_length_b                   7.211(1)
_cell_length_c                   13.267(2)
_cell_measurement_reflns_used    17
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.7
_cell_measurement_theta_min      21.2
_cell_volume                     1040.2(3)
_computing_cell_refinement       'CAD4 Express (Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Nonius, 1994)'
_computing_data_reduction        inhouse
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       \q/2\q
_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  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2417
_diffrn_reflns_theta_full        74.25
_diffrn_reflns_theta_max         74.25
_diffrn_reflns_theta_min         3.40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.572
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2297
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0796
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1546P)^2^+0.0877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.2221
_reflns_number_gt                1848
_reflns_number_total             2297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja021327y.cif
_cod_data_source_block           wagn
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4113591