Total Synthesis of N-Acetylglucosamine-1,6-anhydro-N-acetylmuramylpentapeptide and Evaluation of Its Turnover by AmpD from Escherichia coli
Dusan Hesek; Mijoon Lee; Weilie Zhang; Bruce C. Noll; Shahriar Mobashery; Journal of the American Chemical Society 131 (2009) 5187–5193; doi:10.1021/ja808498m

data_4104157
_publ_contact_author_address
;University of Notre Dame
Department of Chemistry and Biochemistry
251 Nieuwland Science Hall
Notre Dame, IN 46556-5670
USA
;
_publ_contact_author_email       mobashery@nd.edu
_publ_contact_author_fax         1(574)6316652
_publ_contact_author_name        'Professor Shahriar Mobashery'
_publ_contact_author_phone       1(574)6312933
_publ_section_title
;
 Total Synthesis of
 N-Acetylglucosamine-1,6-anhydro-N-acetylmuramylpentapeptide and
 Evaluation of Its Turnover by AmpD from Escherichia coli
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5187
_journal_page_last               5193
_journal_paper_doi               10.1021/ja808498m
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C13 H15 I O4'
_chemical_formula_sum            'C13 H15 I O4'
_chemical_formula_weight         362.15
_chemical_name_common
1,6-Anhydro-2-iodo-4-O-benzyl-2-deoxy-\b-D-glucopyranose
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.5770(10)
_cell_angle_beta                 92.433(5)
_cell_angle_gamma                91.599(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1718(4)
_cell_length_b                   7.5275(5)
_cell_length_c                   13.9663(6)
_cell_measurement_reflns_used    8849
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.385
_cell_measurement_theta_min      3.099
_cell_volume                     647.74(7)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.829
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_device_type  'Bruker d8 Apex II CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0093
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8872
_diffrn_reflns_theta_full        35.61
_diffrn_reflns_theta_max         35.61
_diffrn_reflns_theta_min         1.46
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    2.476
_exptl_absorpt_correction_T_max  0.64
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2006). TWINABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.143
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         8872
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.303
_refine_ls_R_factor_all          0.0160
_refine_ls_R_factor_gt           0.0160
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.0316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0584
_reflns_number_gt                8850
_reflns_number_total             8872
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja808498m_si_004.cif
_cod_data_source_block           compound_6
_cod_database_code               4104157