KAHA Ligations That Form Aspartyl Aldehyde Residues as Synthetic Handles for Protein Modification and Purification.
Murar, Claudia E.; Thuaud, Frédéric; Bode, Jeffrey W.; Journal of the American Chemical Society  (2014) 141215094849001–; doi:10.1021/ja511231f

data_4123156
_publ_section_title
;
 KAHA Ligations That Form Aspartyl Aldehyde Residues as Synthetic Handles
 for Protein Modification and Purification.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141215094849001
_journal_paper_doi               10.1021/ja511231f
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H23 Br N2 O5'
_chemical_formula_sum            'C17 H23 Br N2 O5'
_chemical_formula_weight         415.28
_chemical_melting_point          128
_chemical_name_common
'(3S,5S)-tert-butyl 3-((4-bromophenyl)carbamoyl)-5-ethoxyisoxazolidine-2-carboxylate'
_chemical_name_systematic
;
 (3S,5S)-tert-butyl 3-((4-bromophenyl)carbamoyl)-5-ethoxyisoxazolidine-2-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2014-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4779)
;
_cell_angle_alpha                113.201(4)
_cell_angle_beta                 93.127(4)
_cell_angle_gamma                99.011(4)
_cell_formula_units_Z            2
_cell_length_a                   5.6349(7)
_cell_length_b                   12.3583(15)
_cell_length_c                   15.003(2)
_cell_measurement_reflns_used    1712
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      20.53
_cell_measurement_theta_min      2.79
_cell_volume                     940.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    OLEX2
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       '\w and \f 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  0.0375
_diffrn_reflns_av_unetI/netI     0.1103
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8264
_diffrn_reflns_point_group_measured_fraction_full 0.734
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.091
_diffrn_reflns_theta_min         2.787
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  0.7372
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0702 before and 0.0618 after correction.
The Ratio of minimum to maximum transmission is 0.8764.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 1437 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.035(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         5429
_refine_ls_number_restraints     509
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0427
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    0.570
_reflns_Friedel_fraction_max     0.629
_reflns_number_gt                4138
_reflns_number_total             5429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja511231f_si_001.cif
_cod_data_source_block           jb030314_0m
_cod_database_code               4123156
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1B-H1B
 0.91 with sigma of 0.02
 N1A-H1A
 0.91 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates:
 C8A(H8A), C10A(H10A), C10B(H10B), C8B(H8B)
5.b Secondary CH2 refined with riding coordinates:
 C11B(H11A,H11B), C9A(H9AA,H9AB), C9B(H9BA,H9BB), C11A(H11C,H11D)
5.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C2A(H2A), C3A(H3A), C5A(H5A), C3B(H3B), C2B(H2B), C6B(H6B), C5B(H5B)
5.d Fitted hexagon refined as free rotating group:
 C6A(C1A,C2A,C3A,C4A,C5A), C3B(C2B,C1B,C6B,C5B,C4B)
5.e Idealised Me refined as rotating group:
 C14B(H14A,H14B,H14C), C12B(H12A,H12B,H12C), C15B(H15A,H15B,H15C), C15A(H15D,
 H15E,H15F), C16A(H16D,H16E,H16F), C16B(H16A,H16B,H16C), C12A(H12D,H12E,H12F),
 C14A(H14D,H14E,H14F)
;
_olex2_computing_structure_refinement_long 'SHELXL-97 (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'