Hydrogen bond catalysis of mononucleotide ethylation supports non-random DNA alkylations by N-ethyl, N-nitrosourea

The axial (ax.) and equatorial (eq.) diastereomeric forms of phosphate triesters resulting from reactions of N-ethyl, N-nitrosourea with 3 cyclic mononucleotides were analyzed by column liquid chromatography (CLC). Evidence is presented that the 2'OH group of 3', 5'cAMP essentially contributes to the stereoselective eq. alkyl substitution, most probably by hydrogen bonding catalysis. The neighboring group direction of ethylation gives substantial support to non-random DNA alkylations by NEU.