Total Synthesis of [Ψ[C(=S)NH]Tpg4]Vancomycin Aglycon, [Ψ[C(=NH)NH]Tpg4]Vancomycin Aglycon, and Related Key Compounds: Reengineering Vancomycin for Dual d-Ala-d-Ala and d-Ala-d-Lac Binding
Jian Xie; Akinori Okano; Joshua G. Pierce; Robert C. James; Simon Stamm; Christine M. Crane; Dale L. Boger; Journal of the American Chemical Society 134 (2012) 1284–1297; doi:10.1021/ja209937s

data_4117307
_publ_section_title
;
 Total Synthesis of [\Y[C(=S)NH]Tpg4]Vancomycin Aglycon,
 [\Y[C(=NH)NH]Tpg4]Vancomycin Aglycon, and Related Key Compounds:
 Reengineering Vancomycin for Dual d-Ala-d-Ala and d-Ala-d-Lac Binding
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1284
_journal_page_last               1297
_journal_paper_doi               10.1021/ja209937s
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C52 H65 Cl N4 O16 S'
_chemical_formula_weight         1069.59
_chemical_name_systematic
; 
 ? 
;
_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                 95.71(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.745(3)
_cell_length_b                   13.978(3)
_cell_length_c                   27.529(6)
_cell_measurement_reflns_used    9405
_cell_measurement_temperature    148(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.42
_cell_volume                     5646(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      148(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            27680
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.49
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_correction_T_min  0.9466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      0
_exptl_crystal_description       Parallalepiped
_exptl_crystal_F_000             2264
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1387
_refine_ls_number_reflns         16833
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0853
_refine_ls_shift/su_max          0.187
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2130
_refine_ls_wR_factor_ref         0.2284
_reflns_number_gt                13194
_reflns_number_total             16833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja209937s_si_002.cif
_cod_data_source_block           jianlt
_cod_original_cell_volume        5645.7(19)
_cod_database_code               4117307