Development of a New Family of Conformationally Restricted Peptides as Potent Nucleators of β-Turns. Design, Synthesis, Structure, and Biological Evaluation of a β-Lactam Peptide Analogue of Melanostatin
Claudio Palomo; Jesus M. Aizpurua; Ana Benito; José Ignacio Miranda; Raluca M. Fratila; Carlos Matute; Maria Domercq; Federico Gago; Sonsoles Martin-Santamaria; Anthony Linden; Journal of the American Chemical Society 125 (2003) 16243–16260; doi:10.1021/ja038180a

data_4114552
_publ_contact_author_address
; Departamento de Qu\'imica Org\'anica I
   Facultad de Qu\'imica
   Universidad del Pa\'is Vasco
   Apdo 1072
   E-20080 San Sebasti\'an
   Spain
;
_publ_contact_author_email       alinden@oci.unizh.ch
_publ_contact_author_fax         '41 1 635 6812'
_publ_contact_author_name        'Claudio Palomo'
_publ_contact_author_phone       '41 1 635 4228'
_publ_section_title
;
 Development of a New Family of Conformationally Restricted Peptides as
 Potent Nucleators of \b-Turns. Design, Synthesis, Structure, and
 Biological Evaluation of a \b-Lactam Peptide Analogue of Melanostatin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16243
_journal_page_last               16260
_journal_paper_doi               10.1021/ja038180a
_journal_volume                  125
_journal_year                    2003
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H32 N4 O5 '
_chemical_formula_sum            'C19 H32 N4 O5'
_chemical_formula_weight         396.48
_chemical_melting_point          458
_chemical_name_systematic
; (3R)-1-amidomethyl-3-isobutyl-3-[(2S)-1-(tert-butoxycarbonyl)-
pyrrolidin-2-yl-carbonylamino]azetidin-2-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90.0
_cell_angle_beta                 103.05(1)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   9.939(2)
_cell_length_b                   9.160(2)
_cell_length_c                   12.154(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      12.9
_cell_measurement_theta_min      12.0
_cell_volume                     1077.9(4)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1991)
;
_computing_data_reduction
'teXsan (Molecular Structure Corporation, 1999)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'TEXCIF (Linden, 1999)'
_computing_structure_refinement  teXsan
_computing_structure_solution    'SHELXS97 direct methods (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector                 'scintillation counter'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC5R diffractometer'
_diffrn_measurement_method       '\w--2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku RU200 rotating anode generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2774
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.0889
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.22
_refine_ls_abs_structure_details ' ?'
_refine_ls_extinction_coef       0.0000010(2)
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.5380
_refine_ls_goodness_of_fit_ref   1.6140
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     '1/[^2^(F~o~) + (0.005F~o~)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0416
_refine_ls_wR_factor_gt          0.0392
_refine_ls_wR_factor_ref         0.0392
_reflns_number_gt                2159
_reflns_number_total             2625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja038180asi20030828_065724_3.cif
_cod_data_source_block           32
_cod_original_formula_sum        'C19 H32 N4 O5 '
_cod_database_code               4114552