data_20042 ####################### # Entry information # ####################### save_entry_information _Saveframe_category entry_information _Entry_title ; Cyclic Pseudotetrapeptide L-Phe-L-Trp-D-Lys-D-Thr ; _BMRB_accession_number 20042 _BMRB_flat_file_name bmr20042.str _Entry_type new _Submission_date 2008-08-21 _Accession_date 2008-08-21 _Entry_origination author _NMR_STAR_version 2.1.1 _Experimental_method NMR _Details 'This is an unnatural cyclic tetrapeptide derivative with a 1,4-disubstituted 1,2,3-triazole as a trans amide bond surrogate.' loop_ _Author_ordinal _Author_family_name _Author_given_name _Author_middle_initials _Author_family_title 1 Beierle John M. . stop_ loop_ _Saveframe_category_type _Saveframe_category_type_count assigned_chemical_shifts 1 stop_ loop_ _Data_type _Data_type_count "1H chemical shifts" 28 stop_ loop_ _Revision_date _Revision_keyword _Revision_author _Revision_detail 2011-03-15 update BMRB 'PDBj annotated the coordinate file' 2009-06-10 update BMRB 'complete entry citation' 2009-03-06 original author 'original release' stop_ loop_ _Related_BMRB_accession_number _Relationship 20036 'Cyclic Pseudotetrapeptide (7a)' 20037 'Cyclic Pseudotetrapeptide (7b)' 20038 'Cyclic Pseudotetrapeptide (7c)' 20039 'Cyclic Pseudotetrapeptide (7d)' 20040 'Cyclic Pseudotetrapeptide (7e)' 20041 'Cyclic Pseudotetrapeptide (7f)' 20043 'Cyclic Pseudotetrapeptide (7h)' stop_ save_ ############################# # Citation for this entry # ############################# save_entry_citation _Saveframe_category entry_citation _Citation_full . _Citation_title ; Conformationally Homogeneous Heterocyclic Pseudotetrapeptides as Three-Dimensional Scaffolds for Rational Drug Design: Receptor-Selective Somatostatin Analogues ; _Citation_status published _Citation_type journal _CAS_abstract_code . _MEDLINE_UI_code . _PubMed_ID 19266506 loop_ _Author_ordinal _Author_family_name _Author_given_name _Author_middle_initials _Author_family_title 1 Beierle John M. . 2 Horne 'W. Seth' . . 3 'van Maarseveen' Jan H. . 4 Waser Beatrice . . 5 Reubi 'Jean Claude' . . 6 Ghadiri 'M. Reza' . . stop_ _Journal_abbreviation 'Angew. Chem., Int. Ed.' _Journal_volume 48 _Journal_issue 26 _Journal_CSD . _Book_chapter_title . _Book_volume . _Book_series . _Book_ISBN . _Conference_state_province . _Conference_abstract_number . _Page_first 4725 _Page_last 4729 _Year 2009 _Details . save_ ################################## # Molecular system description # ################################## save_assembly _Saveframe_category molecular_system _Mol_system_name 'Cyclic Pseudotetrapeptide' _Enzyme_commission_number . loop_ _Mol_system_component_name _Mol_label 'Cyclic pseudotetrapeptide' $14FWdKdT stop_ _System_molecular_weight . _System_physical_state native _System_oligomer_state ? _System_paramagnetic no _System_thiol_state . _Database_query_date . _Details ; The PHE and THR residues are linked via a 1,2,3-triazole, where the PHE amine is N1 and the THR carbonyl is C4 and C5. The triazole is an amide bond surrogate. It is a 1,4-disubstituted triazole where N1 is the Phe amine and C4 is the Thr carbonyl carbon. ; save_ ######################## # Monomeric polymers # ######################## save_14FWdKdT _Saveframe_category monomeric_polymer _Mol_type polymer _Mol_polymer_class protein _Name_common 14FWdKdT _Molecular_mass . _Mol_thiol_state 'not present' loop_ _Biological_function 'Somatostatin Mimic' stop_ _Details . ############################## # Polymer residue sequence # ############################## _Residue_count 4 _Mol_residue_sequence FWXX loop_ _Residue_seq_code _Residue_label 1 PHE 2 TRP 3 DLY 4 DTH stop_ _Sequence_homology_query_date . _Sequence_homology_query_revised_last_date . save_ ###################### # Polymer residues # ###################### save_chem_comp_DLY _Saveframe_category polymer_residue _Mol_type 'D-PEPTIDE LINKING' _Name_common D-LYSINE _BMRB_code . _PDB_code DLY _Standard_residue_derivative DLY _Molecular_mass 146.188 _Mol_paramagnetic . _Details ; Information obtained from PDB's Chemical Component Dictionary at http://wwpdb-remediation.rutgers.edu/downloads.html Downloaded on Fri Feb 15 18:39:03 2008 ; loop_ _Atom_name _PDB_atom_name _Atom_type _Atom_chirality _Atom_charge _Atom_oxidation_number _Atom_unpaired_electrons N N N N 0 . ? CA CA C R 0 . ? C C C N 0 . ? O O O N 0 . ? CB CB C N 0 . ? CG CG C N 0 . ? CD CD C N 0 . ? CE CE C N 0 . ? NZ NZ N N 0 . ? OXT OXT O N 0 . ? H H H N 0 . ? H2 H2 H N 0 . ? HA HA H N 0 . ? HB2 HB2 H N 0 . ? HB3 HB3 H N 0 . ? HG2 HG2 H N 0 . ? HG3 HG3 H N 0 . ? HD2 HD2 H N 0 . ? HD3 HD3 H N 0 . ? HE2 HE2 H N 0 . ? HE3 HE3 H N 0 . ? HZ1 HZ1 H N 0 . ? HZ2 HZ2 H N 0 . ? HXT HXT H N 0 . ? stop_ loop_ _Bond_order _Bond_atom_one_atom_name _Bond_atom_two_atom_name _PDB_bond_atom_one_atom_name _PDB_bond_atom_two_atom_name SING N CA ? ? SING N H ? ? SING N H2 ? ? SING CA C ? ? SING CA CB ? ? SING CA HA ? ? DOUB C O ? ? SING C OXT ? ? SING CB CG ? ? SING CB HB2 ? ? SING CB HB3 ? ? SING CG CD ? ? SING CG HG2 ? ? SING CG HG3 ? ? SING CD CE ? ? SING CD HD2 ? ? SING CD HD3 ? ? SING CE NZ ? ? SING CE HE2 ? ? SING CE HE3 ? ? SING NZ HZ1 ? ? SING NZ HZ2 ? ? SING OXT HXT ? ? stop_ save_ save_chem_comp_DTH _Saveframe_category polymer_residue _Mol_type 'D-PEPTIDE LINKING' _Name_common D-THREONINE _BMRB_code . _PDB_code DTH _Standard_residue_derivative DTH _Molecular_mass 119.119 _Mol_paramagnetic . _Details ; Information obtained from PDB's Chemical Component Dictionary at http://wwpdb-remediation.rutgers.edu/downloads.html Downloaded on Fri Feb 15 18:44:42 2008 ; loop_ _Atom_name _PDB_atom_name _Atom_type _Atom_chirality _Atom_charge _Atom_oxidation_number _Atom_unpaired_electrons N N N N 0 . ? CA CA C R 0 . ? CB CB C S 0 . ? CG2 CG2 C N 0 . ? OG1 OG1 O N 0 . ? C C C N 0 . ? O O O N 0 . ? OXT OXT O N 0 . ? H H H N 0 . ? HN2 HN2 H N 0 . ? HA HA H N 0 . ? HB HB H N 0 . ? HG21 HG21 H N 0 . ? HG22 HG22 H N 0 . ? HG23 HG23 H N 0 . ? HG1 HG1 H N 0 . ? HXT HXT H N 0 . ? stop_ loop_ _Bond_order _Bond_atom_one_atom_name _Bond_atom_two_atom_name _PDB_bond_atom_one_atom_name _PDB_bond_atom_two_atom_name SING N CA ? ? SING N H ? ? SING N HN2 ? ? SING CA CB ? ? SING CA C ? ? SING CA HA ? ? SING CB CG2 ? ? SING CB OG1 ? ? SING CB HB ? ? SING CG2 HG21 ? ? SING CG2 HG22 ? ? SING CG2 HG23 ? ? SING OG1 HG1 ? ? DOUB C O ? ? SING C OXT ? ? SING OXT HXT ? ? stop_ save_ #################### # Natural source # #################### save_natural_source _Saveframe_category natural_source loop_ _Mol_label _Organism_name_common _NCBI_taxonomy_ID _Superkingdom _Kingdom _Genus _Species _Details $14FWdKdT . . . . . . 'not a natural peptide' stop_ save_ ######################### # Experimental source # ######################### save_experimental_source _Saveframe_category experimental_source loop_ _Mol_label _Production_method _Host_organism_name_common _Genus _Species _Strain _Vector_name $14FWdKdT 'recombinant technology' . . . . . stop_ save_ ##################################### # Sample contents and methodology # ##################################### ######################## # Sample description # ######################## save_sample_1 _Saveframe_category sample _Sample_type solution _Details . loop_ _Mol_label _Concentration_value _Concentration_value_units _Concentration_min_value _Concentration_max_value _Isotopic_labeling $14FWdKdT . mM 7 12 'natural abundance' stop_ save_ ############################ # Computer software used # ############################ save_CNS _Saveframe_category software _Name CNS _Version . loop_ _Vendor _Address _Electronic_address 'Brunger, Adams, Clore, Gros, Nilges and Read' . . stop_ loop_ _Task 'structure solution' stop_ _Details . save_ ######################### # Experimental detail # ######################### ################################## # NMR Spectrometer definitions # ################################## save_spectrometer_1 _Saveframe_category NMR_spectrometer _Manufacturer Bruker _Model DRX _Field_strength 600 _Details . save_ ############################# # NMR applied experiments # ############################# save_2D_1H-1H_ROESY_1 _Saveframe_category NMR_applied_experiment _Experiment_name '2D 1H-1H ROESY' _Sample_label $sample_1 save_ save_2D_1H-1H_TOCSY_2 _Saveframe_category NMR_applied_experiment _Experiment_name '2D 1H-1H TOCSY' _Sample_label $sample_1 save_ ####################### # Sample conditions # ####################### save_sample_conditions_1 _Saveframe_category sample_conditions _Details . loop_ _Variable_type _Variable_value _Variable_value_error _Variable_value_units temperature 295 . K pH . . pH stop_ save_ #################### # NMR parameters # #################### ############################## # Assigned chemical shifts # ############################## ################################ # Chemical shift referencing # ################################ save_chemical_shift_reference_1 _Saveframe_category chemical_shift_reference _Details . loop_ _Mol_common_name _Atom_type _Atom_isotope_number _Atom_group _Chem_shift_units _Chem_shift_value _Reference_method _Reference_type _External_reference_sample_geometry _External_reference_location _External_reference_axis _Indirect_shift_ratio DSS H 1 'methyl protons' ppm 0.00 internal direct . . . 1.000000000 stop_ save_ ################################### # Assigned chemical shift lists # ################################### ################################################################### # Chemical Shift Ambiguity Index Value Definitions # # # # The values other than 1 are used for those atoms with different # # chemical shifts that cannot be assigned to stereospecific atoms # # or to specific residues or chains. # # # # Index Value Definition # # # # 1 Unique (including isolated methyl protons, # # geminal atoms, and geminal methyl # # groups with identical chemical shifts) # # (e.g. ILE HD11, HD12, HD13 protons) # # 2 Ambiguity of geminal atoms or geminal methyl # # proton groups (e.g. ASP HB2 and HB3 # # protons, LEU CD1 and CD2 carbons, or # # LEU HD11, HD12, HD13 and HD21, HD22, # # HD23 methyl protons) # # 3 Aromatic atoms on opposite sides of # # symmetrical rings (e.g. TYR HE1 and HE2 # # protons) # # 4 Intraresidue ambiguities (e.g. LYS HG and # # HD protons or TRP HZ2 and HZ3 protons) # # 5 Interresidue ambiguities (LYS 12 vs. LYS 27) # # 6 Intermolecular ambiguities (e.g. ASP 31 CA # # in monomer 1 and ASP 31 CA in monomer 2 # # of an asymmetrical homodimer, duplex # # DNA assignments, or other assignments # # that may apply to atoms in one or more # # molecule in the molecular assembly) # # 9 Ambiguous, specific ambiguity not defined # # # ################################################################### save_assigned_chem_shift_list_1 _Saveframe_category assigned_chemical_shifts _Details 'The proton located at C5 on the triazole ring has the value of 7.966 ppm.' loop_ _Experiment_label '2D 1H-1H ROESY' '2D 1H-1H TOCSY' stop_ loop_ _Sample_label $sample_1 stop_ _Sample_conditions_label $sample_conditions_1 _Chem_shift_reference_set_label $chemical_shift_reference_1 _Mol_system_component_name 'Cyclic pseudotetrapeptide' _Text_data_format . _Text_data . loop_ _Atom_shift_assign_ID _Residue_author_seq_code _Residue_seq_code _Residue_label _Atom_name _Atom_type _Chem_shift_value _Chem_shift_value_error _Chem_shift_ambiguity_code 1 1 1 PHE HA H 5.243 . 1 2 1 1 PHE HB2 H 3.727 . 2 3 1 1 PHE HB3 H 3.727 . 2 4 1 1 PHE HD1 H 7.274 . 3 5 1 1 PHE HD2 H 7.274 . 3 6 2 2 TRP H H 7.93 . 1 7 2 2 TRP HA H 4.376 . 1 8 2 2 TRP HB2 H 2.965 . 2 9 2 2 TRP HB3 H 2.965 . 2 10 3 3 DLY H H 7.796 . 1 11 3 3 DLY HA H 4.107 . 1 12 3 3 DLY HB2 H 1.531 . 2 13 3 3 DLY HB3 H 1.531 . 2 14 3 3 DLY HD2 H 1.451 . 2 15 3 3 DLY HD3 H 1.451 . 2 16 3 3 DLY HE2 H 2.674 . 2 17 3 3 DLY HE3 H 2.674 . 2 18 3 3 DLY HG2 H 1.146 . 2 19 3 3 DLY HG3 H 1.146 . 2 20 3 3 DLY HZ1 H 7.622 . 1 21 3 3 DLY HZ2 H 7.622 . 1 22 3 3 DLY HZ3 H 7.622 . 1 23 4 4 DTH H H 7.297 . 1 24 4 4 DTH HA H 4.667 . 1 25 4 4 DTH HB H 4.086 . 1 26 4 4 DTH HG21 H 1.113 . 1 27 4 4 DTH HG22 H 1.113 . 1 28 4 4 DTH HG23 H 1.113 . 1 stop_ save_