Purine nucleoside phosphorylase. Catalytic mechanism and transition-state analysis of the arsenolysis reaction

Biochemistry ◽  
1993 ◽  
Vol 32 (48) ◽  
pp. 13212-13219 ◽  
Author(s):  
Paul C. Kline ◽  
Vern L. Schramm
Keyword(s):  
Transition State ◽  
Purine Nucleoside Phosphorylase ◽  
Catalytic Mechanism ◽  
Purine Nucleoside ◽  
Nucleoside Phosphorylase ◽  
State Analysis

Linear Free Energy Relationships for N(7)-Substituted Guanosines as Substrates of Calf Spleen Purine Nucleoside Phosphorylase. Possible Role of N(7)-Protonation as an Intermediary in Phosphorolysis

1993 ◽  
Vol 48 (9-10) ◽  
pp. 803-811 ◽  
Author(s):  
Agnieszka Bzowska ◽  
Ewa Kulikowska ◽  
David Shugar
Keyword(s):  
Acid Hydrolysis ◽  
Purine Nucleoside Phosphorylase ◽  
Catalytic Mechanism ◽  
Enzymatic Reaction ◽  
Purine Nucleoside ◽  
Nucleoside Phosphorylase ◽  
Linear Free Energy ◽  
Repair Enzymes ◽  
Substrate Properties ◽  
Energy Relationships

Abstract Quantitative structure-activity relationships (QSAR) for a series of N(7)-substituted guanosines as substrates for calf spleen purine nucleoside phosphorylase (PNP) were developed, and compared with those for acid hydrolysis of these analogues. There is no correlation between the rates for enzymatic phosphorolysis and acid hydrolysis, indicating that for the enzymatic reaction labilization of the glycosidic bond is not the only, nor the predominant, effect of N(7)-substitution. Multiple regression analysis of the enzymatic process revealed that optimal substrate properties (minimal Michaelis constant) are associated with the Taft electronic constant equal zero and a substituent size, parametrized by the Taft steric constant, smaller than that for a methyl group. These results support the hypothesis of protonation of the N(7)-position of the base by the enzyme as a catalytic mechanism for calf spleen PNP. Attention is drawn to the postulated similar mechanism of action of other purine N-glycosidases, including plant antiviral proteins which function as RNAN-glycosidases, and possibly some DNA N-glycosidases which function as repair enzymes

Purine Nucleoside Phosphorylase fromMycobacterium tuberculosis. Analysis of Inhibition by a Transition-State Analogue and Dissection by Parts†

Biochemistry ◽  
2001 ◽  
Vol 40 (28) ◽  
pp. 8196-8203 ◽  
Author(s):  
Luiz A. Basso ◽  
Diogenes S. Santos ◽  
Wuxian Shi ◽  
Richard H. Furneaux ◽  
Peter C. Tyler ◽  
...  
Keyword(s):  
Transition State ◽  
Purine Nucleoside Phosphorylase ◽  
Purine Nucleoside ◽  
Nucleoside Phosphorylase ◽  
Transition State Analogue

Purine Nucleoside Phosphorylase. 2. Catalytic Mechanism†

Biochemistry ◽  
1997 ◽  
Vol 36 (39) ◽  
pp. 11735-11748 ◽  
Author(s):  
Mark D. Erion ◽  
Johanna D. Stoeckler ◽  
Wayne C. Guida ◽  
Richard L. Walter
Keyword(s):  
Purine Nucleoside Phosphorylase ◽  
Catalytic Mechanism ◽  
Purine Nucleoside ◽  
Nucleoside Phosphorylase

Atomic Dissection of the Hydrogen Bond Network for Transition-State Analogue Binding to Purine Nucleoside Phosphorylase†

Biochemistry ◽  
2002 ◽  
Vol 41 (49) ◽  
pp. 14489-14498 ◽  
Author(s):  
Greg A. Kicska ◽  
Peter C. Tyler ◽  
Gary B. Evans ◽  
Richard H. Furneaux ◽  
Wuxian Shi ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Transition State ◽  
Purine Nucleoside Phosphorylase ◽  
Purine Nucleoside ◽  
Hydrogen Bond Network ◽  
Nucleoside Phosphorylase ◽  
Transition State Analogue ◽  
Bond Network

Synthesis of Transition State Analogue Inhibitors for Purine Nucleoside Phosphorylase and N-Riboside Hydrolases

Tetrahedron ◽  
2000 ◽  
Vol 56 (19) ◽  
pp. 3053-3062 ◽  
Author(s):  
Gary B. Evans ◽  
Richard H. Furneaux ◽  
Graeme J. Gainsford ◽  
Vern L. Schramm ◽  
Peter C. Tyler
Keyword(s):  
Transition State ◽  
Purine Nucleoside Phosphorylase ◽  
Purine Nucleoside ◽  
Nucleoside Phosphorylase ◽  
Transition State Analogue ◽  
Transition State Analogue Inhibitors

scholarly journals l-Enantiomers of Transition State Analogue Inhibitors Bound to Human Purine Nucleoside Phosphorylase

2008 ◽  
Vol 130 (3) ◽  
pp. 842-844 ◽  
Author(s):  
Agnes Rinaldo-Matthis ◽  
Andrew S. Murkin ◽  
Udupi A. Ramagopal ◽  
Keith Clinch ◽  
Simon P. H. Mee ◽  
...  
Keyword(s):  
Transition State ◽  
Purine Nucleoside Phosphorylase ◽  
Purine Nucleoside ◽  
Nucleoside Phosphorylase ◽  
Transition State Analogue ◽  
Transition State Analogue Inhibitors
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