Effect of a <i>cis</i>-4-aminopiperidine-3-carboxylic acid (<i>cis</i>-APiC) residue on mixed-helical folding of unnatural peptides.
Choi, Sunglim; Shim, Jihyun; Kang, Philjae; Choi, Soo Hyuk; Organic & biomolecular chemistry 20 (2022) 613–618; doi:10.1039/d1ob02223g

data_7158452
_publ_section_title
;
 Effect of a <i>cis</i>-4-aminopiperidine-3-carboxylic acid
 (<i>cis</i>-APiC) residue on mixed-helical folding of unnatural peptides.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              613
_journal_page_last               618
_journal_paper_doi               10.1039/d1ob02223g
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C35 H54 N6 O10 S, C H Cl3'
_chemical_formula_sum            'C36 H55 Cl3 N6 O10 S'
_chemical_formula_weight         870.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796)
;
_audit_update_record
;
2019-06-14 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6129(8)
_cell_length_b                   16.6129(6)
_cell_length_c                   27.4345(16)
_cell_measurement_reflns_used    1198
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.31
_cell_measurement_theta_min      3.11
_cell_volume                     4381.2(5)
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14985
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         72.665
_diffrn_reflns_theta_min         3.110
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.834
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.5863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0843 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.7781.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.045(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         8006
_refine_ls_number_restraints     432
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0643
_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^)+(0.0621P)^2^+1.4150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.903
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                5464
_reflns_number_total             8006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02223g2.cif
_cod_data_source_block           Ala-ACHC-Ala-APiC-Ala_moon229
_cod_depositor_comments
'Adding full bibliography for 7158451--7158453.cif.'
_cod_database_code               7158452
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H6A(0.043) H3A(0.043) H4(0.037) H1(0.05) H5(0.037) H23A(0.078)
 H23B(0.078) H23C(0.078) H12(0.04) H7A(0.039) H7B(0.039) H30(0.071) H15(0.042)
 H28A(0.103) H28B(0.103) H28C(0.103) H6(0.038) H27A(0.095) H27B(0.095)
 H27C(0.095) H4A(0.109) H4B(0.109) H4C(0.109) H26A(0.087) H26B(0.087)
 H26C(0.087) H20(0.044) H16A(0.065) H16B(0.065) H13A(0.064) H13B(0.064)
 H13C(0.064) H17A(0.075) H17B(0.075) H19A(0.058) H19B(0.058) H18A(0.078)
 H18B(0.078) H9A(0.049) H9B(0.049) H31(0.083) H8A(0.047) H8B(0.047) H1A(0.128)
 H1B(0.128) H1C(0.128) H10(0.04) H33A(0.149) H33B(0.149) H33C(0.149) H22(0.041)
 H34(0.081) H35(0.065) H3(0.056) H2S(0.065) H1S(0.109)
 Fixed X: H6A(-0.2946) H3A(-0.0493) H4(0.0321) H1(-0.0924) H5(0.0409) H23A(-
 0.163) H23B(-0.2921) H23C(-0.1453) H12(0.0956) H7A(-0.2116) H7B(-0.2239) H30(-
 0.2779) H15(0.2428) H28A(-0.4664) H28B(-0.368) H28C(-0.3749) H6(-0.2434) H27A(-
 0.2714) H27B(-0.1934) H27C(-0.3591) H4A(-0.0716) H4B(0.0851) H4C(0.0295) H26A(-
 0.1146) H26B(-0.0446) H26C(-0.1076) H20(0.2716) H16A(0.4716) H16B(0.4674)
 H13A(-0.1773) H13B(-0.0876) H13C(-0.1413) H17A(0.609) H17B(0.4863)
 H19A(0.2665) H19B(0.2675) H18A(0.4974) H18B(0.4864) H9A(0.1373) H9B(0.136)
 H31(-0.4131) H8A(0.1529) H8B(0.0173) H1A(-0.2736) H1B(-0.3071) H1C(-0.1948)
 H10(-0.1054) H33A(-0.4249) H33B(-0.3109) H33C(-0.4358) H22(-0.171) H34(-
 0.1281) H35(0.0133) H3(0.0351) H2S(0.4558) H1S(0.488)
 Fixed Y: H6A(-0.2145) H3A(0.0895) H4(-0.0278) H1(0.1396) H5(-0.0521) H23A(-
 0.2361) H23B(-0.1755) H23C(-0.1504) H12(0.1044) H7A(0.2918) H7B(0.2318)
 H30(0.3444) H15(-0.1051) H28A(-0.2562) H28B(-0.3326) H28C(-0.2911) H6(0.1636)
 H27A(-0.1586) H27B(-0.1128) H27C(-0.1216) H4A(0.0698) H4B(0.0785) H4C(-0.0068)
 H26A(-0.315) H26B(-0.229) H26C(-0.2788) H20(-0.1439) H16A(-0.1192) H16B(-
 0.0414) H13A(0.0467) H13B(0.0215) H13C(0.1122) H17A(-0.021) H17B(0.044) H19A(-
 0.0504) H19B(0.0224) H18A(-0.0029) H18B(-0.0944) H9A(0.2555) H9B(0.1912)
 H31(0.4596) H8A(0.3206) H8B(0.35) H1A(-0.181) H1B(-0.1355) H1C(-0.2066)
 H10(0.2483) H33A(0.6122) H33B(0.6553) H33C(0.6061) H22(-0.0837) H34(0.5806)
 H35(0.4667) H3(-0.0053) H2S(0.2216) H1S(0.154)
 Fixed Z: H6A(-0.0112) H3A(0.0013) H4(-0.0594) H1(0.1604) H5(0.0432)
 H23A(0.0683) H23B(0.0713) H23C(0.0942) H12(-0.1117) H7A(0.089) H7B(0.1346)
 H30(0.2205) H15(-0.0518) H28A(-0.1514) H28B(-0.1426) H28C(-0.1952) H6(0.0584)
 H27A(-0.208) H27B(-0.1645) H27C(-0.1637) H4A(0.2386) H4B(0.2197) H4C(0.2385)
 H26A(-0.134) H26B(-0.1432) H26C(-0.188) H20(0.0286) H16A(-0.0294) H16B(-
 0.0637) H13A(-0.0905) H13B(-0.1372) H13C(-0.1314) H17A(0.0066) H17B(0.0032)
 H19A(0.094) H19B(0.0556) H18A(0.0832) H18B(0.0652) H9A(0.0195) H9B(0.063)
 H31(0.2241) H8A(0.0976) H8B(0.0683) H1A(0.171) H1B(0.221) H1C(0.22) H10(0.013)
 H33A(0.1574) H33B(0.191) H33C(0.2155) H22(0.0195) H34(0.1469) H35(0.1444)
 H3(0.1522) H2S(0.1306) H1S(0.1291)
;