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. 2003 Jan 2;46(1):155-60.
doi: 10.1021/jm0203332.

8-Aza-immucillins as Transition-State Analogue Inhibitors of Purine Nucleoside Phosphorylase and Nucleoside Hydrolases

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8-Aza-immucillins as Transition-State Analogue Inhibitors of Purine Nucleoside Phosphorylase and Nucleoside Hydrolases

Gary B Evans et al. J Med Chem. .

Abstract

The 8-aza-immucillins (8-aza-9-deazapurines linked from C9 to C1 of 1,4-dideoxy-1,4-iminoribitol) have been designed as transition-state analogues of the reactions catalyzed by purine nucleoside phosphorylase and nucleoside hydrolases. Syntheses of the 8-aza-immucillin analogues of inosine and adenosine are described. They are powerful inhibitors of the target enzymes with equilibrium dissociation constants as low as 42 pM.

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