Impact of β-Perfluoroalkyl Substitution of Proline on the Proteolytic Stability of Its Peptide Derivatives
Chernykh, Anton V.; Aloshyn, Danylo; Kuchkovska, Yuliya O.; Daniliuc, Constantin Gabriel; Tolmachova, Nataliya A.; Kondratov, Ivan S.; Zozulya, Sergiy X.; Grygorenko, Oleksandr O.; Haufe, Guenter; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01430K

data_7158879
_publ_section_title
;
 Impact of \b-Perfluoroalkyl Substitution of Proline on the Proteolytic
 Stability of Its Peptide Derivatives
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01430K
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H25 F5 N2 O4'
_chemical_formula_weight         452.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           'APEX3 v2016.1-0'
_audit_update_record
;
2022-08-01 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2877(3)
_cell_length_b                   16.4671(6)
_cell_length_c                   21.5393(8)
_cell_measurement_reflns_used    6415
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.4573
_cell_measurement_theta_min      3.3784
_cell_volume                     2230.18(16)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.2419
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39243
_diffrn_reflns_theta_full        66.86
_diffrn_reflns_theta_max         66.86
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    1.052
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.240
_refine_ls_abs_structure_details
;

Flack x determined using 857 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(19)
_refine_ls_extinction_coef       0.00098(17)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0210P)^2^+1.7196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                2849
_reflns_number_total             3960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01430k2.cif
_cod_data_source_block           dan9441_2R3S-5b
_cod_database_code               7158879
_shelx_res_checksum              70820
_shelx_hkl_checksum              88387