Model peptides containing the 3-sulfanyl-norbornene amino acid, a conformationally constrained cysteine analogue effective inducer of 310-helix secondary structures
Clerici, Francesca; Ruffoni, Alessandro; Contini, Alessandro; Soave, Raffaella; Lo Presti, Leonardo; Esposto, Irene; nava, donatella; Pellegrino, Sara; Gelmi, Maria Luisa; maffucci, irene; RSC Adv.  (2015) –; doi:10.1039/C5RA03805G

data_7220026
_publ_section_title
;
 Model peptides containing the 3-sulfanyl-norbornene amino acid, a
 conformationally constrained cysteine analogue effective inducer of
 310-helix secondary structures
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA03805G
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H42 N6 O6 S'
_chemical_formula_sum            'C30 H42 N6 O6 S'
_chemical_formula_weight         614.75
_chemical_name_systematic
;
(1S,2S,3S,4R)-2-((S)-2-acetamidopropanamido)-N-((S)-1-((1-(((S)-1-amino-1-
oxopropan-2-yl)amino)-2-methyl-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)-3-
(benzylthio)bicyclo[2.2.1]hept-5-ene-2-carboxamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             15/02/2014
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-02-28 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.63(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.829(2)
_cell_length_b                   9.0852(18)
_cell_length_c                   31.098(6)
_cell_measurement_reflns_used    9823
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      47.42
_cell_measurement_theta_min      4.67
_cell_volume                     3340.7(11)
_computing_cell_refinement       'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_data_collection       'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_data_reduction        'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_molecular_graphics    'Diamond v3.2i (Brandenburg, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX CCD area-detector'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            72594
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.825
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 2004'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
  Flack x determined using 4302 quotients [(I+)-(I-)]/[(I+)+(I-)]
  (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.0021(6)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     788
_refine_ls_number_reflns         15364
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.1731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.881
_reflns_number_gt                11336
_reflns_number_total             15364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra03805g2.cif
_cod_data_source_block           compound4b
_cod_original_cell_volume        3340.7(12)
_cod_database_code               7220026