Pyrrolidine nucleotide analogs with a tunable conformation

Abstract

Conformational preferences of the pyrrolidine ring in nucleotide analogs 7–14 were investigated by means of NMR and molecular modeling. The effect of the relative configuration of hydroxy and nucleobase substituents as well as the effect of the alkylation or acylation of the pyrrolidine nitrogen atom on the conformation of the pyrrolidine ring were studied. The results of a conformational analysis show that the alkylation/acylation can be effectively used for tuning the pyrrolidine conformation over the whole pseudorotation cycle.

Keywords

• conformation
• NMR
• nucleic acids
• nucleotide analog
• phosphonic acid
• pseudorotation
• pyrrolidine