(1S,2R/1R,2S)-Aminocyclohexyl Glycyl Thymine PNA: Synthesis, Monomer Crystal Structures, and DNA/RNA Hybridization Studies
- 29 July 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (17) , 3013-3016
- https://doi.org/10.1021/ol034933m
Abstract
The synthesis of ethyl cis-(1S,2R/1R,2S)-2-aminocyclohex-1-yl-N-(thymin-1-yl-acetyl) glycinate (10a and 10b) via enzymatic resolution of the key racemic intermediate trans-2-azido cyclohexanols 3 is reported. The crystal structures of 10 show equatorial disposition of the tertiary amide group, with the torsion angle β in the range 60−70°. The PNA oligomers incorporating these show differential effects in hybridizing with complementary DNA and RNA.Keywords
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