Design and stereoselective synthesis of four peptide nucleic acid monomers with cyclic structures in backbone |
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| Authors: | Akiko Watanabe Naotoshi Kiyota Tetsuo Yamasaki Kazuhiro Tanda Tatsunori Miyagoe Masanori Sakamoto Masami Otsuka |
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| Affiliation: | 1. School of Pharmaceutical Sciences, Kyushu University of Health and Welfare, Nobeoka, Miyazaki 882‐8508, Japan;2. Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Kumamoto, Kumamoto 862‐0973, Japan |
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| Abstract: | Four isomers of the monomer of peptide nucleic acid (PNA) were derived from (2S,4R)‐4‐hydroxyproline; they had different stereochemistries at the C2 and C4 positions in the pyrrolidine ring. These different backbone conformations corresponding to four different stereochemistries were realized through a combination of inversions at the C2 and the C4 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). |
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