Polyamide based nucleic acid analogs synthesis of δ-amino acids with nucleic acid bases bearing side chains

Article abstract of DOI:10.1016/S0960-894X(97)00172-8

Nucleoamino acids of type I-III have been synthesized, which can serve as building blocks for novel polyamide based nucleic acid analogs. Key steps in the syntheses are the alkylation of serinol I and homoserinol 18 with tert-butyl bromoacetate or tert-butyl bromopropionate under phase transfer conditions and the introduction of thymine or uracil into the amino acid side drains by way of a Mitsunobu reaction. Cytosine derivatives were prepared through uracil → cytosine base conversion at the stage of N(δ)-BOC protected amino acid tert-butyl esters.