Scalable synthesis of γ-thiolysine starting from lysine and a side by side comparison with δ-thiolysine in non-enzymatic ubiquitination
Merkx, Remco; de Bruin, Gerjan; Kruithof, Art; van den Bergh, Toine; Snip, Erwin; Lutz, Martin; El Oualid, Farid; Ovaa, Huib; Chemical Science 4 (2013) 4494–; doi:10.1039/c3sc51599k

data_1514617
_publ_section_title
;
 Scalable synthesis of \g-thiolysine starting from lysine and a side by
 side comparison with \d-thiolysine in non-enzymatic ubiquitination
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              4494
_journal_paper_doi               10.1039/c3sc51599k
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H31 Cl N2 O6'
_chemical_formula_sum            'C17 H31 Cl N2 O6'
_chemical_formula_weight         394.89
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   32.591(3)
_cell_length_b                   32.591(3)
_cell_length_c                   5.1877(5)
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.29
_cell_measurement_theta_min      2.71
_cell_volume                     4772.0(8)
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_collection       Proteum
_computing_data_reduction        'SAINT V7.68A'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.851
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker proteum'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.851
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            29955
_diffrn_reflns_point_group_measured_fraction_full 0.841
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         61.509
_diffrn_reflns_theta_min         1.565
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.5940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2012/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       needle
_exptl_crystal_F_000             1908
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.006(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     725
_refine_ls_number_reflns         9698
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.5530P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.978
_reflns_Friedel_fraction_full    0.832
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                8880
_reflns_number_total             9698
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3sc51599k.txt
_cod_data_source_block           l0516a
_cod_original_cell_volume        4772.1(9)
_cod_database_code               1514617
_shelxl_version_number           2012-9
_shelx_res_checksum              17798
_shelx_hkl_checksum              80470