Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr Cofactor of Cytochrome c Oxidase
Maximillian E. Mahoney; Allen Oliver; Ólöf Einarsdóttir; Joseph P. Konopelski; Journal of Organic Chemistry 74 (2009) 8212–8218; doi:10.1021/jo901744y

data_4024959
_publ_contact_author_address     '379 PSB'
_publ_contact_author_email       mahoney@chemistry
_publ_contact_author_name        'Max Mahoney'
_publ_contact_author_phone       9-4669
_publ_section_title
;
Synthesis of a Cyclic Pentapeptide Mimic of the Active Site His-Tyr
Cofactor of Cytochrome c Oxidase
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8212
_journal_page_last               8218
_journal_paper_doi               10.1021/jo901744y
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C36 H45 N7 O7, C2 O2 F3, C2 H6 O S, 3(H2 O)'
_chemical_formula_sum            'C40 H57 F3 N7 O13 S'
_chemical_formula_weight         932.99
_chemical_name_systematic
; 
 ? 
;
_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                90.00
_cell_angle_beta                 91.943(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.482(5)
_cell_length_b                   15.891(8)
_cell_length_c                   14.949(8)
_cell_measurement_reflns_used    2168
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      2.72
_cell_volume                     2251(2)
_computing_cell_refinement       'Bruker SAINT v7.34A'
_computing_data_collection       'Bruker APEX-II v2.1-4'
_computing_data_reduction        'Bruker SAINT v7.34A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       \w/2\q-scans
_diffrn_radiation_monochromator  'channel-cut Si-<111> crystal'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.77490
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.1349
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9554
_diffrn_reflns_theta_full        25.55
_diffrn_reflns_theta_max         25.55
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9757
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             986
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         6343
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1504
_refine_ls_R_factor_gt           0.0845
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1361P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1995
_refine_ls_wR_factor_ref         0.2432
_reflns_number_gt                3668
_reflns_number_total             6343
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901744y_si_002.cif
_cod_data_source_block           xsc08051
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4024959