Polymerization of amino acids containing nucleotide bases.
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. When 3 or 4 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 of 3 did not act as templates to facilitate the oligomerization of 4.
Cheikh
A B
AB
Salk Institute for Biological Studies, San Diego, California 92138.
Orgel
L E
LE
D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D000596:Amino Acids / Q000138:chemical synthesis; D000613:Aminobutyrates / Q000138:chemical synthesis; D055598:Chemical Phenomena; D002621:Chemistry; D015394:Molecular Structure; D009711:Nucleotides / Q000138:chemical synthesis; D011072:Poly U; D011108:Polymers; D014498:Uracil / Q000031:analogs & derivatives / Q000138:chemical synthesis
D000596:Amino Acids; D000613:Aminobutyrates; D009711:Nucleotides; D011108:Polymers; C064304:1-(3'-amino-3'-carboxypropyl)adenine; D011072:Poly U; D014498:Uracil; C064303:1-(3'-amino-3'-carboxypropyl)uracil; D000225:Adenine