1RXP

STRUCTURE OF TRYPSIN (ORTHORHOMBIC) WITH 1-(4-TERT-BUTYLCARBAMOYL- PIPERAZINE-1-CARBONYL)-3-(3-GUANIDINO-PROPYL)-4-OXO-AZETIDINE-2-CARBOXYLIC ACID


Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 1.70 Å
  • R-Value Free: 0.222 
  • R-Value Work: 0.195 
  • R-Value Observed: 0.195 

wwPDB Validation   3D Report Full Report


Ligand Structure Quality Assessment 


This is version 1.2 of the entry. See complete history


Literature

Solid-phase synthesis and SAR of 4-carboxy-2-azetidinone mechanism-based tryptase inhibitors

Sutton, J.C.Bolton, S.A.Davis, M.E.Hartl, K.S.Jacobson, B.Mathur, A.Ogletree, M.L.Slusarchyk, W.A.Zahler, R.Seiler, S.M.Bisacchi, G.S.

(2004) Bioorg Med Chem Lett 14: 2233-2239

  • DOI: https://doi.org/10.1016/j.bmcl.2004.02.012
  • Primary Citation of Related Structures:  
    1RXP

  • PubMed Abstract: 

    A series of nonguanidine N1-activated C4-carboxy azetidinone tryptase inhibitors was prepared by solid-phase methodology to quickly assess the SAR associated with distal functionality on the N1-activating group. From these studies, potent inhibitors with improved specificity were discovered.


  • Organizational Affiliation

    The Bristol-Myers Squibb Pharmaceutical Research Institute, PO Box 4000, Princeton, NJ 08543-4000, USA. james.sutton@bms.com


Macromolecules
Find similar proteins by:  (by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
TRYPSIN223Bos taurusMutation(s): 0 
EC: 3.4.21.4
UniProt
Find proteins for P00760 (Bos taurus)
Explore P00760 
Go to UniProtKB:  P00760
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupP00760
Sequence Annotations
Expand
  • Reference Sequence
Small Molecules
Ligands 3 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
169
Query on 169

Download Ideal Coordinates CCD File 
D [auth A]1-(4-TERT-BUTYLCARBAMOYL-PIPERAZINE-1-CARBONYL)-3-(3-GUANIDINO-PROPYL)-4-OXO-AZETIDINE-2-CARBOXYLIC ACID
C18 H33 N7 O5
BVNQCAHTTOIOEK-STQMWFEESA-N
SO4
Query on SO4

Download Ideal Coordinates CCD File 
C [auth A]SULFATE ION
O4 S
QAOWNCQODCNURD-UHFFFAOYSA-L
CA
Query on CA

Download Ideal Coordinates CCD File 
B [auth A]CALCIUM ION
Ca
BHPQYMZQTOCNFJ-UHFFFAOYSA-N
Binding Affinity Annotations 
IDSourceBinding Affinity
169 PDBBind:  1RXP IC50: 72 (nM) from 1 assay(s)
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 1.70 Å
  • R-Value Free: 0.222 
  • R-Value Work: 0.195 
  • R-Value Observed: 0.195 
  • Space Group: P 21 21 21
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 54.29α = 90
b = 58.25β = 90
c = 66.68γ = 90
Software Package:
Software NamePurpose
DENZOdata reduction
SCALEPACKdata scaling
AMoREphasing
X-PLORrefinement

Structure Validation

View Full Validation Report



Ligand Structure Quality Assessment 


Entry History 

Deposition Data

Revision History  (Full details and data files)

  • Version 1.0: 2004-06-08
    Type: Initial release
  • Version 1.1: 2008-04-29
    Changes: Version format compliance
  • Version 1.2: 2011-07-13
    Changes: Version format compliance