Literature DB >> 18154341

L-Enantiomers of transition state analogue inhibitors bound to human purine nucleoside phosphorylase.

Agnes Rinaldo-Matthis1, Andrew S Murkin, Udupi A Ramagopal, Keith Clinch, Simon P H Mee, Gary B Evans, Peter C Tyler, Richard H Furneaux, Steven C Almo, Vern L Schramm.   

Abstract

Human purine nucleoside phosphorylase (PNP) was crystallized with transition-state analogue inhibitors Immucillin-H and DADMe-Immucillin-H synthesized with ribosyl mimics of l-stereochemistry. The inhibitors demonstrate that major driving forces for tight binding of these analogues are the leaving group interaction and the cationic mimicry of the transition state, even though large geometric changes occur with d-Immucillins and l-Immucillins bound to human PNP.

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Year:  2007        PMID： 18154341      PMCID： PMC2531256          DOI： 10.1021/ja710733g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  17 in total

1.  Ionic states of substrates and transition state analogues at the catalytic sites of N-ribosyltransferases.

Authors:  Anthony A Sauve; Sean M Cahill; Stephan G Zech; Luiz A Basso; Andrzej Lewandowicz; Diogenes S Santos; Charles Grubmeyer; Gary B Evans; Richard H Furneaux; Peter C Tyler; Ann McDermott; Mark E Girvin; Vern L Schramm
Journal:  Biochemistry       Date:  2003-05-20       Impact factor: 3.162

2.  Three-dimensional structure of human erythrocytic purine nucleoside phosphorylase at 3.2 A resolution.

Authors:  S E Ealick; S A Rule; D C Carter; T J Greenhough; Y S Babu; W J Cook; J Habash; J R Helliwell; J D Stoeckler; R E Parks
Journal:  J Biol Chem       Date:  1990-01-25       Impact factor: 5.157

3.  Neighboring group participation in the transition state of human purine nucleoside phosphorylase.

Authors:  Andrew S Murkin; Matthew R Birck; Agnes Rinaldo-Matthis; Wuxian Shi; Erika A Taylor; Steven C Almo; Vern L Schramm
Journal:  Biochemistry       Date:  2007-04-04       Impact factor: 3.162

4.  Tight-binding inhibitors--IV. Inhibition of adenosine deaminases by various inhibitors.

Authors:  R P Agarwal; T Spector; R E Parks
Journal:  Biochem Pharmacol       Date:  1977-03-01       Impact factor: 5.858

5.  Transition state structure of purine nucleoside phosphorylase and principles of atomic motion in enzymatic catalysis.

Authors:  A Fedorov; W Shi; G Kicska; E Fedorov; P C Tyler; R H Furneaux; J C Hanson; G J Gainsford; J Z Larese; V L Schramm; S C Almo
Journal:  Biochemistry       Date:  2001-01-30       Impact factor: 3.162

6.  Achieving the ultimate physiological goal in transition state analogue inhibitors for purine nucleoside phosphorylase.

Authors:  Andrzej Lewandowicz; Peter C Tyler; Gary B Evans; Richard H Furneaux; Vern L Schramm
Journal:  J Biol Chem       Date:  2003-07-03       Impact factor: 5.157

7.  One-third-the-sites transition-state inhibitors for purine nucleoside phosphorylase.

Authors:  R W Miles; P C Tyler; R H Furneaux; C K Bagdassarian; V L Schramm
Journal:  Biochemistry       Date:  1998-06-16       Impact factor: 3.162

8.  Transition state analysis for human and Plasmodium falciparum purine nucleoside phosphorylases.

Authors:  Andrzej Lewandowicz; Vern L Schramm
Journal:  Biochemistry       Date:  2004-02-17       Impact factor: 3.162

9.  Spontaneous epimerization of (S)-deoxycoformycin and interaction of (R)-deoxycoformycin, (S)-deoxycoformycin, and 8-ketodeoxycoformycin with adenosine deaminase.

Authors:  V L Schramm; D C Baker
Journal:  Biochemistry       Date:  1985-01-29       Impact factor: 3.162

10.  Nucleoside-phosphorylase deficiency in a child with severely defective T-cell immunity and normal B-cell immunity.

Authors:  E R Giblett; A J Ammann; D W Wara; R Sandman; L K Diamond
Journal:  Lancet       Date:  1975-05-03       Impact factor: 79.321
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  9 in total

1.  Altered enthalpy-entropy compensation in picomolar transition state analogues of human purine nucleoside phosphorylase.

Authors:  Achelle A Edwards; Jennifer M Mason; Keith Clinch; Peter C Tyler; Gary B Evans; Vern L Schramm
Journal:  Biochemistry       Date:  2009-06-16       Impact factor: 3.162

2.  A beta-fluoroamine inhibitor of purine nucleoside phosphorylase.

Authors:  Jennifer M Mason; Andrew S Murkin; Lei Li; Vern L Schramm; Graeme J Gainsford; Brian W Skelton
Journal:  J Med Chem       Date:  2008-09-25       Impact factor: 7.446

3.  Catalytic site conformations in human PNP by 19F-NMR and crystallography.

Authors:  Javier Suarez; Antti M Haapalainen; Sean M Cahill; Meng-Chiao Ho; Funing Yan; Steven C Almo; Vern L Schramm
Journal:  Chem Biol       Date:  2013-02-21

4.  Third-generation immucillins: syntheses and bioactivities of acyclic immucillin inhibitors of human purine nucleoside phosphorylase.

Authors:  Keith Clinch; Gary B Evans; Richard F G Fröhlich; Richard H Furneaux; Peter M Kelly; Laurent Legentil; Andrew S Murkin; Lei Li; Vern L Schramm; Peter C Tyler; Anthony D Woolhouse
Journal:  J Med Chem       Date:  2009-02-26       Impact factor: 7.446

5.  Ribocation transition state capture and rebound in human purine nucleoside phosphorylase.

Authors:  Mahmoud Ghanem; Andrew S Murkin; Vern L Schramm
Journal:  Chem Biol       Date:  2009-09-25

6.  Tight binding enantiomers of pre-clinical drug candidates.

Authors:  Gary B Evans; Scott A Cameron; Andreas Luxenburger; Rong Guan; Javier Suarez; Keisha Thomas; Vern L Schramm; Peter C Tyler
Journal:  Bioorg Med Chem       Date:  2015-07-30       Impact factor: 3.641

7.  Loop-tryptophan human purine nucleoside phosphorylase reveals submillisecond protein dynamics.

Authors:  Mahmoud Ghanem; Nickolay Zhadin; Robert Callender; Vern L Schramm
Journal:  Biochemistry       Date:  2009-04-28       Impact factor: 3.162

8.  The ligand binding mechanism to purine nucleoside phosphorylase elucidated via molecular dynamics and machine learning.

Authors:  Sergio Decherchi; Anna Berteotti; Giovanni Bottegoni; Walter Rocchia; Andrea Cavalli
Journal:  Nat Commun       Date:  2015-01-27       Impact factor: 14.919

9.  Natural Products as New Treatment Options for Trichomoniasis: A Molecular Docking Investigation.

Authors:  Mary Snow Setzer; Kendall G Byler; Ifedayo Victor Ogungbe; William N Setzer
Journal:  Sci Pharm       Date:  2017-01-27
  9 in total

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