Oligonucleotides and nucleotidopeptides. XLII. Efficacy of the intramolecular influence of the carboxy groups of amino acids in nucleotidyl-(P → N)-amino acids (peptides) as a function of their positions
It has been established that remote carboxy groups in nucleotidyl-(5′ → N)-β-alanine and -alanylalanine do not affect the mechanism of the cleavage of the phosphoramide center. The situation is different in the case of nucleotidyl-(5′ → Nɛ)-lysine. It has been shown that in the 3′-phenylalanine derivative of dTMP, the influence of the α-carboxy group of the amino acid is only half as great as in the 5′-analog. The α-carboxy groups of the amino acids in oligonucleotidyl-(Pin → N)-amino acids also weaken the mechanism of the cleavage of the phosphoramide centers.
KeywordsCarboxy Group Hydrolytic Stability Phosphoramide Amino Acid Ester Carbonyldiimidazole
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