DNA-, RNA- and self-pairing properties of a pyrrolidinyl peptide nucleic acid with a (2′R,4′S)-prolyl-(1S,2S)-2-aminocyclopentanecarboxylic acid backbone

✍ Scribed by Jaru Taechalertpaisarn; Pitchanun Sriwarom; Chalotorn Boonlua; Nattawut Yotapan; Chotima Vilaivan; Tirayut Vilaivan

• Book ID: 104098273
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 404 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.08.102

✦ Synopsis

A new pyrrolidinyl peptide nucleic acid (PNA) comprising of an alternate sequence of 4 0 -nucleobasemodified proline with (2 0 R,4 0 S) configuration and a (1S,2S)-2-aminocyclopentanecarboxylic acid [(2 0 R,4 0 S)-acpcPNA] backbone was synthesized and its DNA-, RNA-and self-pairing properties studied. T m and CD studies suggested that the (2 0 R,4 0 S)-acpcPNA forms antiparallel hybrids to DNA and RNA with high sequence and direction specificity. The stability of these hybrids is comparable to those of the (2 0 R,4 0 R)-acpcPNA hybrids previously reported by our group. On the other hand, experiments with a self-complementary sequence indicated that the new (2 0 R,4 0 S)-acpcPNA forms a more stable antiparallel self-hybrid than (2 0 R,4 0 R)-acpcPNA.