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_4114550
_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         'C25 H37 N3 O6'
_chemical_formula_sum            'C25 H37 N3 O6'
_chemical_formula_weight         475.58
_chemical_melting_point          424
_chemical_name_systematic
;
(3S,4R)-1-(3-aza-4-carboxy-4-methyl-2-oxopentyl)-3-benzyl-3-
tert-butoxicarbonylamino-4-isobutylazetidin-2-one
;
_space_group_IT_number           154
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      154
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             02-01-20
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   15.0005(1)
_cell_length_b                   15.0005(1)
_cell_length_c                   21.8165(2)
_cell_measurement_reflns_used    3132
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.0
_cell_volume                     4251.35(6)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\f and \w scans with \k offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'Nonius FR591 sealed tube generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            85545
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.87
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.0796
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack & Bernardinelli (2000)'
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_coef       0.0153(11)
_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   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.1975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                4561
_reflns_number_total             5578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja038180asi20030828_065724_1.cif
_cod_data_source_block           11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom & difmap' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 32 2 1 '
_cod_database_code               4114550