Literature DB >> 18778937

Immucillins in custom catalytic-site cavities.

Andrew S Murkin1, Keith Clinch, Jennifer M Mason, Peter C Tyler, Vern L Schramm.   

Abstract

Neighboring-group participation in the reaction catalyzed by purine nucleoside phosphorylase involves a compression mode between the 5'- and 4'-ribosyl oxygens, facilitated by His257. The His257Gly mutant opens a space in the catalytic site. Hydrophobic 5'-substituted Immucillins are transition-state analogue inhibitors of this mutant enzyme. Dissociation constants as low as 2pM are achieved, with K(m)/K(d) as high as 400,000,000.

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Year:  2008        PMID： 18778937      PMCID： PMC2614083          DOI： 10.1016/j.bmcl.2008.08.047

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  13 in total

1.  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

2.  Energetic mapping of transition state analogue interactions with human and Plasmodium falciparum purine nucleoside phosphorylases.

Authors:  Andrzej Lewandowicz; Erika A Taylor Ringia; Li-Min Ting; Kami Kim; Peter C Tyler; Gary B Evans; Olga V Zubkova; Simon Mee; Gavin F Painter; Dirk H Lenz; Richard H Furneaux; Vern L Schramm
Journal:  J Biol Chem       Date:  2005-06-16       Impact factor: 5.157

3.  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

Review 4.  Enzymatic transition states and transition state analog design.

Authors:  V L Schramm
Journal:  Annu Rev Biochem       Date:  1998       Impact factor: 23.643

5.  Addition of lithiated 9-deazapurine derivatives to a carbohydrate cyclic imine: convergent synthesis of the aza-C-nucleoside immucillins.

Authors:  G B Evans; R H Furneaux; T L Hutchison; H S Kezar; P E Morris; V L Schramm; P C Tyler
Journal:  J Org Chem       Date:  2001-08-24       Impact factor: 4.354

6.  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

7.  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

8.  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

Review 9.  Purine nucleoside phosphorylase deficiency.

Authors:  M L Markert
Journal:  Immunodefic Rev       Date:  1991

10.  Synthesis of a transition state analogue inhibitor of purine nucleoside phosphorylase via the Mannich reaction.

Authors:  Gary B Evans; Richard H Furneaux; Peter C Tyler; Vern L Schramm
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005
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  7 in total

1.  Methylthioinosine phosphorylase from Pseudomonas aeruginosa. Structure and annotation of a novel enzyme in quorum sensing.

Authors:  Rong Guan; Meng-Chiao Ho; Steven C Almo; Vern L Schramm
Journal:  Biochemistry       Date:  2011-01-25       Impact factor: 3.162

2.  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

3.  On the Origin of the Chemical Barrier and Tunneling in Enzymes.

Authors:  Sara Quaytman Machleder; Exequiel T Pineda; Steven D Schwartz
Journal:  J Phys Org Chem       Date:  2010-07-01       Impact factor: 2.391

4.  Enzymatic transition states and dynamic motion in barrier crossing.

Authors:  Steven D Schwartz; Vern L Schramm
Journal:  Nat Chem Biol       Date:  2009-08       Impact factor: 15.040

5.  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

6.  Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics.

Authors:  Keith Clinch; Gary B Evans; Richard F G Fröhlich; Shivali A Gulab; Jemy A Gutierrez; Jennifer M Mason; Vern L Schramm; Peter C Tyler; Anthony D Woolhouse
Journal:  Bioorg Med Chem       Date:  2012-07-14       Impact factor: 3.641

Review 7.  Mannich bases in medicinal chemistry and drug design.

Authors:  Gheorghe Roman
Journal:  Eur J Med Chem       Date:  2014-10-30       Impact factor: 6.514
  7 in total

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