A Simple Nucleic Acid Alternative: Aminopropyl Nucleic Acids (APNAs)

Abstract

Aminopropyl nucleic acids are constitutionally simple nucleic acids alternatives with one chiral center per nucleotide and with the constitutional potential to hybridize with RNA. Both R and S isomers of the 3′-or 2′-aminopropyl nucleosides were incorporated either into DNA or likewise were used for fully modified sequences. The (R)-adenine analogue, yielding (S)-APNA, can be considered as a candidate for universal base pairing.

Keywords:

• Aminopropyl nucleosides
• antisense oligonucleotides
• nucleoside phosphoramidates

Notes

¹Introduction of the 3′-amine changes the priority rules, but attachment of a phosphate at the nitrogen atom affords (S)-APNA from (R)-acyclic blocks.