Chemoenzymatic synthesis of 3-deoxy-3-fluoro-l-fucose and its enzymatic incorporation into glycoconjugates.
Valverde, Pablo; Vendeville, Jean-Baptiste; Hollingsworth, Kristian; Mattey, Ashley P.; Keenan, Tessa; Chidwick, Harriet; Ledru, Helene; Huonnic, Kler; Huang, Kun; Light, Mark E.; Turner, Nicholas; Jiménez-Barbero, Jesús; Galan, M. Carmen; Fascione, Martin A.; Flitsch, Sabine; Turnbull, W. Bruce; Linclau, Bruno; Chemical communications (Cambridge, England) 56 (2020) 6408–6411; doi:10.1039/d0cc02209h

data_7126458
_publ_section_title
;
 Chemoenzymatic synthesis of 3-deoxy-3-fluoro-l-fucose and its enzymatic
 incorporation into glycoconjugates.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6408
_journal_page_last               6411
_journal_paper_doi               10.1039/d0cc02209h
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C6 H11 F O4'
_chemical_formula_sum            'C6 H11 F O4'
_chemical_formula_weight         166.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-13 deposited with the CCDC.	2020-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.908(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1522(3)
_cell_length_b                   4.7390(2)
_cell_length_c                   9.7711(4)
_cell_measurement_reflns_used    4101
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6840
_cell_measurement_theta_min      4.5240
_cell_volume                     371.86(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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    -55.00  70.00   1.00    2.00    --  -19.30  60.00 120.00  125
  2  \w    -55.00  70.00   1.00    2.00    --  -19.30  57.00  60.00  125
  3  \w   -109.00  13.00   1.00    2.00    --  -19.30 -38.00-150.00  122
  4  \w    -52.00  70.00   1.00    2.00    --  -19.30  38.00-180.00  122
  5  \w   -109.00   7.00   1.00    2.00    --  -19.30 -60.00   0.00  116
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0581441000
_diffrn_orient_matrix_UB_12      0.0041564000
_diffrn_orient_matrix_UB_13      -0.0462298000
_diffrn_orient_matrix_UB_21      -0.0663775000
_diffrn_orient_matrix_UB_22      0.0136276000
_diffrn_orient_matrix_UB_23      -0.0569703000
_diffrn_orient_matrix_UB_31      0.0042962000
_diffrn_orient_matrix_UB_32      0.1490264000
_diffrn_orient_matrix_UB_33      0.0065583000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5611
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.493
_diffrn_reflns_theta_min         3.011
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.18b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       prism
_exptl_crystal_F_000             176
_exptl_crystal_recrystallization_method
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1895
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0434P)^2^+0.0652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0791
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1854
_reflns_number_total             1895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02209h2.cif
_cod_data_source_block           2019sot0012_k1_100k
_cod_depositor_comments          'Adding full bibliography for 7126458.cif.'
_cod_database_code               7126458
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C6H11F1O4
_chemical_oxdiff_usercomment     3F-fucose
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3A), C4(H4A), C5(H5)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              2042
_olex2_date_sample_submission    2019-05-21
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id 3F-fucose
_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 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.424