Polymerization of amino acids containing nucleotide bases

Summary We have prepared the nucleoamino acids 1-(3-amino, 3-carboxypropyl)uracil (3) and 9-(3-amino, 3-carboxypropyl)adenine (4) as (l)-enantiomers and as racemic mixtures. When3 or4 is suspended in water and treated with N,N-carbonyldiimidazole, peptides are formed in good yield. The products formed from the (l)-enantiomers are hydrolyzed to the monomeric amino acids by pronase.Attempts to improve the efficiency of these oligomerizations by including a polyuridylate template in the reaction mixture were not successful. Similarly, oligomers derived from the (l)-enantiomer of3 did not act as templates to facilitate the oligomerization of4.