Enzyme Inhibitors. VI. Studies on the Bulk Tolerance of Adenosine Deaminase for 6-Substituted Amino-9-(3-hydroxypropyl)purines

In order to study the ability of the enzyme adenosine deaminase to tolerate bulk at the 6-position of certain purine nucleoside analogs, several 6-substituted amino-9-(3-hydroxypropyl)purines were prepared. These compounds were synthesized by allowing 6-chloro-9-(3-hydroxypropyl)purine to react with the appropriate amines. Enzymatic evaluation of these compounds revealed that increasing the size of the substituent on the 6-amino group decreased the inhibitory property of the compound. These results establish that adenosine deaminase has little bulk tolerance for substituents on the 6-amino group of the purine nucleus.