H. Schaeffer, C. F. Schwender, R. Johnson
Jul 1, 1965
Citations
0
Influential Citations
4
Citations
Quality indicators
Journal
Journal of pharmaceutical sciences
Abstract
To study the mode of binding to adenosine deaminase by the hydroxyl group of 9-(2-hydroxyethyl)- and 9-(3-hydroxypropyl)adenines, a variety of 9-(2-methoxyethyl)-, 9-(3-methoxypropyl)-6-substituted purines and 9-(acetoxyalkyl)adenines were synthesized. Enzymatic evaluation of these compounds as inhibitors of adenosine deaminase revealed that they were less inhibitory than the corresponding compounds with a free hydroxyl group. These data indicate that the mode of binding of the hydroxyl group on the alkyl chain at the 9-position of adenine is by means of a hydrogen bond and that the structure of the hydrogen bond is from the hydrogen of the hydroxyl group on the inhibitor to an electronegative atom on the enzyme.