Design and Synthesis of a Novel Class of Sugar-Peptide Hybrids: C-Linked Glyco β-Amino Acids through a Stereoselective "Acetate" Mannich Reaction as the Key Strategic Element
Claudio Palomo; Mikel Oiarbide; Aitor Landa; M. Concepción González-Rego; Jesús M. García; Alberto González; José M. Odriozola; Manuel Martín-Pastor; Anthony Linden; Journal of the American Chemical Society 124 (2002) 8637–8643; doi:10.1021/ja026250s

data_4114967
_publ_contact_author_address
; Departamento de Qu\'imica Org\'anica I
  Facultad de Qu\'imica
  Universidad del Pa\'is Vasco
  Apdo 1072
  E-20080 San Sebasti\'an
  Spain
;
_publ_contact_author_email       alinden@oci.unizh.ch
_publ_contact_author_fax         '41 1 635 6812'
_publ_contact_author_name        'Claudio Palomo'
_publ_contact_author_phone       '41 1 635 4228'
_publ_section_title
;
 Design and Synthesis of a Novel Class of Sugar-Peptide Hybrids: C-Linked
 Glyco \b-Amino Acids through a Stereoselective "Acetate" Mannich Reaction
 as the Key Strategic Element
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8637
_journal_page_last               8643
_journal_paper_doi               10.1021/ja026250s
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C35 H61 N O9 Si '
_chemical_formula_sum            'C35 H61 N O9 Si'
_chemical_formula_weight         667.94
_chemical_melting_point          375(1)
_chemical_name_systematic
; (1R)-2-endo-[(3S)-3-tert-butoxycarbonylamino-5-
(2:3,4:6-di-O-isopropyliden-\a-D-glucopyranosylpentanoyl]-2-
exo-trimethylsilyloxy-1,7,7-trimethylbicyclo[2.2.1]heptane
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2002-02-28
_cell_angle_alpha                90.0
_cell_angle_beta                 95.2206(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.3795(1)
_cell_length_b                   12.4469(1)
_cell_length_c                   29.6317(2)
_cell_measurement_reflns_used    9129
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     3812.32(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'TEXCIF (Linden, 1999)'
_computing_structure_refinement
'teXsan (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SIR92 direct methods (Altomare et al., 1994)'
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 '65 mm CCD camera on \k goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1.909
_diffrn_measured_fraction_theta_max 1.909
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\w scans with \k offsets'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.073
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            98102
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.21
_refine_ls_abs_structure_details ' Flack (1983)'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_coef       0.00000052(6)
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.2990
_refine_ls_goodness_of_fit_ref   1.4600
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     837
_refine_ls_number_reflns         10821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     '1/[^2^(F~o~) + (0.005F~o~)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0367
_refine_ls_wR_factor_gt          0.0320
_refine_ls_wR_factor_ref         0.0320
_reflns_number_gt                10821
_reflns_number_total             17437
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja026250s_s2.cif
_cod_data_source_block           35_(L0208)
_cod_original_formula_sum        'C35 H61 N O9 Si '
_cod_database_code               4114967