Unusual substrates for adenosine deaminase from calf intestinal mucosa.

A number of adenine nucleosides with exocyclic double bonds either at the 4',5' position in pentofuranosyl nucleosides or at the 5',6' position of hexofuranosyl nucleosides have been found to act as substrates for adenosine deaminase (adenosine aminohydrolase, EC 3.5.4.4) from calf intestinal mucosa. Most of the results obtained are contrary to the accepted minimal structural requirements for substrate activity. These nucleosides had either incorrect anomeric configurations or no hydroxyl group at C-5' or C-3' in the proper configuration; some compounds incorporated both structural changes. There is a possiblity that the unsaturated group has a special role in binding to the enzyme.