DERIVATIVES OF 3-DEOXY-3-(N-HYDROXYAMINO)-D-RIBOSE

A series of clopentylidene-3-deoxy-5-O-toluoyl-alpha-D-riboses has bee n prepared. The blocking groups used were chosen to allow an easy nucl eosidation of these compounds to spin labelled analogs of natural nucl eosides. The conformational behavior of the N-arylmethyl-N-hydroxyamin o group has been studied using 3J(CH) NMR coupling data and molecular mechanics computations. Upon spontaneous oxidation, these hydroxylamin es led to the corresponding aminoxyl free radicals which were submitte d to EPR spectroscopy and quantum mechanical computations at a semiemp irical level (PM3).