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Design and stereoselective synthesis of four peptide nucleic acid monomers with cyclic structures in backbone
Author(s) -
Watanabe Akiko,
Kiyota Naotoshi,
Yamasaki Tetsuo,
Tanda Kazuhiro,
Miyagoe Tatsunori,
Sakamoto Masanori,
Otsuka Masami
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.627
Subject(s) - chemistry , monomer , peptide nucleic acid , pyrrolidine , thymine , nucleic acid , ring (chemistry) , stereochemistry , peptide , antiparallel (mathematics) , stereoselectivity , dna , organic chemistry , polymer , biochemistry , physics , quantum mechanics , magnetic field , catalysis
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).