Design and stereoselective synthesis of four peptide nucleic acid monomers with cyclic structures in backbone

✍ Scribed by Akiko Watanabe; Naotoshi Kiyota; Tetsuo Yamasaki; Kazuhiro Tanda; Tatsunori Miyagoe; Masanori Sakamoto; Masami Otsuka

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2011
• Tongue: English
• Weight: 199 KB
• Volume: 48
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.627

✦ Synopsis

Abstract

Four isomers of the monomer of peptide nucleic acid (PNA) were derived from (2__S__,4__R__)‐4‐hydroxyproline; they had different stereochemistries at the C^2^ and C^4^ positions in the pyrrolidine ring. These different backbone conformations corresponding to four different stereochemistries were realized through a combination of inversions at the C^2^ and the C^4^ positions in pyrrolidine ring. The obtained backbone frameworks were reacted with N‐benzoyl thymine to give the corresponding PNA monomers. Spectroscopic comparison of the resultant monomers confirmed their stereochemistries. J. Heterocyclic Chem., (2011).