Synthesis and Conformational Studies of Peptidomimetics Containing a New Bifunctional Diketopiperazine Scaffold Acting as a β-Hairpin Inducer
Ana Sofia M. Ressurreição; Andrea Bordessa; Monica Civera; Laura Belvisi; Cesare Gennari; Umberto Piarulli; Journal of Organic Chemistry 73 (2008) 652–660; doi:10.1021/jo702072z

data_4023198
_publ_section_title
;
 Synthesis and Conformational Studies of Peptidomimetics Containing
 a New Bifunctional Diketopiperazine Scaffold Acting
 as a \b-Hairpin Inducer
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              652
_journal_page_last               660
_journal_paper_doi               10.1021/jo702072z
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C17 H20 N2 O5'
_chemical_formula_sum            'C17 H20 N2 O5'
_chemical_formula_weight         332.35
_chemical_name_systematic
;
[(2S,5S)-4-Benzyl-5-hydroxymethyl-3,6-dioxo-piperazin-2-yl]-acetic acid
allyl ester
;
_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                 99.71(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.394(4)
_cell_length_b                   10.764(19)
_cell_length_c                   10.800(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      10.6
_cell_measurement_theta_min      7.5
_cell_volume                     847.2(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.761
_diffrn_measured_fraction_theta_max 0.761
_diffrn_measurement_device_type  'Enraf Nonius CAD4 automated diffractometer'
_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  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1327
_diffrn_reflns_theta_full        25.22
_diffrn_reflns_theta_max         25.22
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         1230
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0916P)^2^+0.0854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                854
_reflns_number_total             1230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702072z-File003.cif
_cod_data_source_block           compound3b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023198