Design, Synthesis, and Hybridisation of Water-Soluble, Peptoid Nucleic Acid Oligomers Tagged with Thymine
✍ Scribed by Rosa Zarra; Daniela Montesarchio; Cinzia Coppola; Giuseppe Bifulco; Simone Di Micco; Irene Izzo; Francesco De Riccardis
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 471 KB
- Volume
- 2009
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
The preparation of a new class of backbone‐modified PNA mimetic incorporating thymine is described. Target dipeptoid monomer 21 was synthesised from an N‐[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 22. A possible reason could reside in the concurrent unfavourable influence of the anionic N‐(carboxymethyl) moieties and the flexible nucleobase/backbone ethylene linker.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)