Chemistry and pharmacology of apiose. 7. Susceptibility of some branched chain sugar nucleosides to enzymatic deamination

Article abstract of DOI:10.1021/jm00256a005

The synthesis of a new branched chain sugar nucleoside 9 (5 deoxy 3 C hydroxymethyl β D xylofuranosyl) adenine is described. This compound and 9 (3 C hydroxymethyl α L threofuranosyl) adenine are substrates of calf adenosine deaminase whereas the 3' epimer of the second compound is not deaminated. This shows that a C 3' carbon ramification on a nucleoside does not always abolish susceptibility to enzymatic deamination and that the configuration at the branching point plays an important role in substrate specificity.