Beta-turn modified gramicidin S analogues containing arylated sugar amino acids display antimicrobial and hemolytic activity comparable to the natural product.
Grotenbreg, Gijsbert M; Buizert, Annelies E M; Llamas-Saiz, Antonio L; Spalburg, Emile; van Hooft, Peter A V; de Neeling, Albert J; Noort, Daan; van Raaij, Mark J; van der Marel, Gijsbert A; Overkleeft, Herman S; Overhand, Mark; Journal of the American Chemical Society 128 (2006) 7559–7565; doi:10.1021/ja0588510

data_4101496
_publ_section_title
;
 Beta-turn modified gramicidin S analogues containing arylated sugar
 amino acids display antimicrobial and hemolytic activity comparable to
 the natural product.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7559
_journal_page_last               7565
_journal_paper_doi               10.1021/ja0588510
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_formula_analytical     C63H95N11O12
_chemical_formula_moiety         'C63 H95 N11 O12, O33.5'
_chemical_formula_sum            'C63 H95 N11 O45.5'
_chemical_formula_weight         1734.505
_chemical_name_common            abp02
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           179
_symmetry_cell_setting           hexagonal
_symmetry_Int_Tables_number      179
_symmetry_space_group_name_Hall  'P 65 2 (0 0 1)'
_symmetry_space_group_name_H-M   'P 65 2 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-12-22T18:08:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            12
_cell_length_a                   40.8437(3)
_cell_length_b                   40.8437(3)
_cell_length_c                   28.72400(10)
_cell_measurement_temperature    100.0(1)
_cell_volume                     41497.9(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics
'PyMOL (DeLano, 2002) DeLano Scientific, San Carlos, CA, USA.'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD Mosaic'
_diffrn_measurement_method       'oscillation camera'
_diffrn_radiation_monochromator  'double mirror'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.97565
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            164496
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        29.23
_diffrn_reflns_theta_max         29.23
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             10968.0
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.629
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1312
_refine_ls_number_reflns         14213
_refine_ls_number_restraints     1903
_refine_ls_restrained_S_all      1.583
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.1152
_refine_ls_shift/su_max          0.127
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3249
_refine_ls_wR_factor_ref         0.3391
_reflns_number_gt                12767
_reflns_number_total             14213
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0588510si20051231_041631.cif
_cod_data_source_block           abp02
_cod_original_sg_symbol_Hall     'P 65 2 ( 0 0 1 )'
_cod_database_code               4101496