β-Hydroxy-Stabilized Boron-Nitrogen Heterocycles Enable Rapid and Efficient C-Terminal Protein Modification.
Gu, Han; Ghosh, Saptarshi; Staples, Richard J.; Bane, Susan L.; Bioconjugate chemistry 30 (2019) 2604–2613; doi:10.1021/acs.bioconjchem.9b00534

data_1552499
_publ_section_title
;
 \b-Hydroxy-Stabilized Boron-Nitrogen Heterocycles Enable Rapid and
 Efficient C-Terminal Protein Modification.
;
_journal_issue                   10
_journal_name_full               'Bioconjugate chemistry'
_journal_page_first              2604
_journal_page_last               2613
_journal_paper_doi               10.1021/acs.bioconjchem.9b00534
_journal_volume                  30
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 B N3 O4'
_chemical_formula_sum            'C18 H16 B N3 O4'
_chemical_formula_weight         349.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.8770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.20330(10)
_cell_length_b                   8.90940(10)
_cell_length_c                   16.9484(2)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.04
_cell_measurement_theta_min      2.61
_cell_volume                     1689.57(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18758
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.068
_diffrn_reflns_theta_min         2.610
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0642 before and 0.0499 after correction. The Ratio of minimum to maximum transmission is 0.8876. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method 'Used as received'
_exptl_crystal_size_max          0.502
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 2375 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6315
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1011P)^2^+0.7355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1656
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                5751
_reflns_number_total             6315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            bc9b00534_si_002.cif
_cod_data_source_block           jh1218a
_cod_database_code               1552499
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.688
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2B(H2B)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C12A(H12A,H12B), C3B(H3BA,H3BB), C12B(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C14A(H14A), C15A(H15A),
 C16A(H16A), C17A(H17A), C18A(H18A), C4B(H4B), C7B(H7B), C8B(H8B), C9B(H9B),
 C10B(H10B), C14B(H14B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B)
;
_shelx_res_checksum              72252
_shelx_hkl_checksum              62047
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'Vial 2 CBZ'
_olex2_submission_special_instructions 'No special instructions were received'