Desulfurative modification of cysteine residues in peptides and proteins <i>via</i> the installation and photoexcitation of thieno[2,3-<i>c</i>]-pyrroles.
Chen, Zijing; Wang, Wenjun; Chen, Baicheng; Chen, Si-Cong; Aoken, Aimila; Wu, Fanrui; Zeng, Guihua; Luo, Tuoping; Chemical science 16 (2025) 22091–22100; doi:10.1039/d5sc05199a

data_1576059
_publ_section_title
;
 Desulfurative modification of cysteine residues in peptides and proteins
 <i>via</i> the installation and photoexcitation of
 thieno[2,3-<i>c</i>]-pyrroles.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              22091
_journal_page_last               22100
_journal_paper_doi               10.1039/d5sc05199a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C27 H25 N3 O8 S2'
_chemical_formula_sum            'C27 H25 N3 O8 S2'
_chemical_formula_weight         583.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-12-15 deposited with the CCDC.	2025-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                101.2400(10)
_cell_angle_beta                 99.5740(10)
_cell_angle_gamma                90.1680(10)
_cell_formula_units_Z            2
_cell_length_a                   6.71170(10)
_cell_length_b                   12.01840(10)
_cell_length_c                   17.0450(2)
_cell_measurement_reflns_used    12808
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.7910
_cell_measurement_theta_min      3.7540
_cell_volume                     1328.87(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -62.00 -36.00   0.50    0.05    -- -104.50  57.00   0.00   52
  2  \w    -69.00  24.00   0.50    0.05    --  -48.37  77.00  90.00  186
  3  \w    -39.00  13.00   0.50    0.05    --  -48.37  37.00   0.00  104
  4  \w    -23.00   5.00   0.50    0.05    --  -48.37  19.00 -90.00   56
  5  \w    -61.00 -35.00   0.50    0.05    -- -104.50  57.00-150.00   52
  6  \w    -62.00 -34.00   0.50    0.05    -- -104.50  57.00 120.00   56
  7  \w    -87.00 -44.00   0.50    0.05    -- -104.50  93.00   2.00   86
  8  \w   -108.00 -40.00   0.50    0.05    -- -104.50 111.00  16.03  136
  9  \w   -109.00 -83.00   0.50    0.05    -- -104.50 125.00  30.00   52
 10  \w    -81.00 -55.00   0.50    0.05    -- -104.50 125.00  30.00   52
 11  \w    -47.00  10.00   0.50    0.05    --  -48.37  93.00   2.00  114
 12  \w   -118.00 -88.00   0.50    0.05    -- -104.50 134.00-146.98   60
 13  \w   -131.00 -95.00   0.50    0.05    -- -104.50 -19.00 -90.00   72
 14  \w   -166.00-128.00   0.50    0.05    -- -104.50 -57.00 -60.00   76
 15  \w   -170.00 -91.00   0.50    0.05    -- -104.50 -77.00   0.00  158
 16  \w   -126.00 -95.00   0.50    0.05    -- -104.50 -19.00 -30.00   62
 17  \w   -117.00 -91.00   0.50    0.05    -- -104.50 -57.00 -60.00   52
 18  \w    -69.00 -37.00   0.50    0.05    --  -48.37 -57.00 -90.00   64
 19  \w   -111.00 -71.00   0.50    0.05    --  -48.37 -57.00 -90.00   80
 20  \w   -171.00-114.00   0.50    0.05    -- -104.50 -19.00-150.00  114
 21  \w   -174.00-149.00   0.50    0.05    -- -104.50 -19.00 -90.00   50
 22  \w   -154.00-109.00   0.50    0.05    -- -104.50 -93.00-109.00   90
 23  \w     90.00 118.00   0.50    0.05    --  106.44  77.00 -90.00   56
 24  \w     89.00 168.00   0.50    0.05    --  106.44  93.00   2.00  158
 25  \w    145.00 174.00   0.50    0.05    --  106.44  37.00 -90.00   58
 26  \w    106.00 137.00   0.50    0.05    --  106.44  37.00 -90.00   62
 27  \w    112.00 156.00   0.50    0.05    --  106.44  19.00-180.00   88
 28  \w     78.00 105.00   0.50    0.05    --  106.44 -77.00-120.00   54
 29  \w     39.00 107.00   0.50    0.05    --  106.44-125.00-120.00  136
 30  \w    -24.00  20.00   0.50    0.05    --   48.37 -19.00 -60.00   88
 31  \w     36.00 105.00   0.50    0.05    --  106.44 -99.00 -90.00  138
 32  \w     35.00  61.00   0.50    0.05    --  106.44 -57.00  30.00   52
 33  \w     37.00 107.00   0.50    0.05    --  106.44-125.00 150.00  140
 34  \w     61.00 104.00   0.50    0.05    --  106.44 -99.00 150.00   86
 35  \w     56.00 104.00   0.50    0.05    --  106.44 -99.00  90.00   96
 36  \w    -19.00  77.00   0.50    0.05    --   48.37 -93.00-109.00  192
 37  \w     42.00  68.00   0.50    0.05    --  106.44 -99.00-180.00   52
 38  \w     46.00  72.00   0.50    0.05    --  106.44 -93.00-109.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1355264000
_diffrn_orient_matrix_UB_12      0.1007770000
_diffrn_orient_matrix_UB_13      0.0511988000
_diffrn_orient_matrix_UB_21      0.1209411000
_diffrn_orient_matrix_UB_22      -0.0033085000
_diffrn_orient_matrix_UB_23      -0.0696751000
_diffrn_orient_matrix_UB_31      -0.1458211000
_diffrn_orient_matrix_UB_32      0.0832825000
_diffrn_orient_matrix_UB_33      -0.0356213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15333
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.959
_diffrn_reflns_theta_min         3.752
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.7073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5163
_reflns_number_total             5360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05199a2.cif
_cod_data_source_block           czj_b2_auto
_cod_depositor_comments          'Adding full bibliography for 1576059.cif.'
_cod_database_code               1576059
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.819
_shelx_estimated_absorpt_t_min   0.619
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N16(H16), C5(H5), C6(H6), C8(H8), C24(H24), C25(H25), C27(H27), C28(H28),
 C33(H33), C34(H34), C36(H36), C37(H37)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C31(H31A,H31B,H31C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              989
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.781