Biosynthesis of a bacterial meroterpenoid reveals a non-canonical class II meroterpenoid cyclase.
Wang, Zengyuan; Alsup, Tyler A.; Pan, Xingming; Li, Lu-Lu; Tian, Jupeng; Yang, Ziyi; Lin, Xiaoxu; Xu, Hui-Min; Rudolf, Jeffrey D.; Dong, Liao-Bin; Chemical science 16 (2024) 310–317; doi:10.1039/d4sc06010e

data_1573176
_publ_section_title
;
 Biosynthesis of a bacterial meroterpenoid reveals a non-canonical class
 II meroterpenoid cyclase.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              310
_journal_page_last               317
_journal_paper_doi               10.1039/d4sc06010e
_journal_volume                  16
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H47 N O4, C H4 O'
_chemical_formula_sum            'C31 H51 N O5'
_chemical_formula_weight         517.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2023-11-21 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5566(3)
_cell_length_b                   6.1185(2)
_cell_length_c                   34.8632(8)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.588
_cell_measurement_theta_min      2.536
_cell_volume                     2890.52(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            42594
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.582
_diffrn_reflns_theta_min         2.536
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1373 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.8786.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5296
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0484P)^2^+1.1285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5113
_reflns_number_total             5296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06010e2.cif
_cod_data_source_block           cu_20211102_dzy28_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1573176--1573177.cif.
;
_cod_database_code               1573176
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.929
_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, All O(H) groups
2. Restrained distances
 H13B-H19A
 2 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C4(H4A), C11(H11), C16(H16), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B),
 C20(H20A,H20B), C21(H21A,H21B), C25(H25A,H25B), C26(H26A,H26B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C24(H24)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C17(H17A,H17B,H17C),
 C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C31(H31A,H31B,
 H31C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_shelx_res_checksum              1366
_shelx_hkl_checksum              46438
_olex2_submission_special_instructions 'No special instructions were received'