Formation of i-motifs from acyclic (l)-threoninol nucleic acids

Abstract

Acyclic (l)-threoninol nucleic acids ((l)-aTNA) containing poly-cytosines are prepared and investigated at various pH values, revealing the formation of a highly stable structure at lower pH that have the characteristics of an i-motif.

Xeno nucleic acids (XNAs) having non-ribose scaffolds with unique supramolecular properties

“…The Gothelf group found that L-aTNA forms a stable triplex when a homopyrimidine L-aTNA targets a homo-purine DNA or RNA. 57 The same group also reported that L-aTNAs of appropriate sequence can form G-quartet 58 and i-motif 59 structures. These data suggest that L-aTNA and SNA prefer to form higher-ordered structures.…”

Design and Hybridization Properties of Acyclic Xeno Nucleic Acid Oligomers

“…We also observed unusual triple base pairing, Watson‐Crick C : G and parallel Hoogsteen G*G, in solutions of L‐ a TNA/RNA and SNA/RNA confirmed by crystal structures and mass spectroscopy. Formation of higher‐ordered structures of a TNA such as conventional poly purine/pyrimidine triplex, [51] i‐motif‐like complex, [52] and G‐quadruplex‐like structure [53] were also detected by Gothelf's group. The flexible acyclic scaffold of a TNA apparently allow formation of these non‐canonical structures.…”

Functionalized Acyclic (l)‐Threoninol Nucleic Acid Four‐Way Junction with High Stability In Vitro and In Vivo

“…were the first to report on the synthesis of aTNA and that aTNA forms an antiparallel homo‐duplex of high stability [17, 18] . We have later shown that aTNA forms highly stable sandwich type triplex structures with DNA and RNA and that aTNA is capable of forming i‐motifs and G‐quadruplexes [19–22] . This artificial oligonucleotide furthermore forms parallel duplexes with DNA and RNA, presumably because of an optimal rigidity [17] .…”