Media type: E-Article Title: Design, Synthesis, and Hybridisation of Water‐Soluble, Peptoid Nucleic Acid Oligomers Tagged with Thymine Contributor: Zarra, Rosa; Montesarchio, Daniela; Coppola, Cinzia; Bifulco, Giuseppe; Di Micco, Simone; Izzo, Irene; De Riccardis, Francesco imprint: Wiley, 2009 Published in: European Journal of Organic Chemistry Language: English DOI: 10.1002/ejoc.200900781 ISSN: 1434-193X; 1099-0690 Keywords: Organic Chemistry ; Physical and Theoretical Chemistry Origination: Footnote: Description: <jats:title>Abstract</jats:title><jats:p>The preparation of a new class of backbone‐modified PNA mimetic incorporating thymine is described. Target dipeptoid monomer <jats:bold>21</jats:bold> was synthesised from an <jats:italic>N</jats:italic>‐[2‐(thymin‐1‐yl)ethyl]glycinate ester and a properly protected iminodiacetic acid. The distinctive structural motif in the backbone is acarboxy group, inserted to impart water solubility to the oligomer. Two achiral oligopeptoid sequences (8‐mer and 12‐mer), characterised by the shift of the amide carbonyl group away from the nucleobase, were efficiently assembled according to solid‐phase synthesis protocols. Thermal denaturation studies showed that the two homopyrimidine oligopeptoids do not effectively hybridise with complementary sequences of DNA and RNA or fully synthetic (2,4‐diamino)triazin‐6‐yl‐tagged peptoid <jats:bold>22</jats:bold>. A possible reason could reside in the concurrent unfavourable influence of the anionic <jats:italic>N</jats:italic>‐(carboxymethyl) moieties and the flexible nucleobase/backbone ethylene linker.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)</jats:p>