PNA monomers fully compatible with standard Fmoc-based solid-phase synthesis of pseudocomplementary PNA

  • Bioorg Med Chem Lett. 2017 Aug 1;27(15):3337-3341. doi: 10.1016/j.bmcl.2017.06.015.
Toru Sugiyama  1 ,  Genki Hasegawa  2 ,  Chie Niikura  2 ,  Keiko Kuwata  3 ,  Yasutada Imamura  4 ,  Yosuke Demizu  5 ,  Masaaki Kurihara  6 ,  Atsushi Kittaka  7
Affiliations
  • 1. Faculty of Pharmaceutical Sciences, Teikyo University, Itabashi-ku, Tokyo 173-8605, Japan. Electronic address: [email protected].
  • 2. Faculty of Pharmaceutical Sciences, Teikyo University, Itabashi-ku, Tokyo 173-8605, Japan.
  • 3. Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan.
  • 4. Faculty of Engineering, Kogakuin University, 2665-1 Nakano, Hachioji, Tokyo 192-0015, Japan.
  • 5. Division of Organic Chemistry, National Institute of Health Sciences, Ministry of Health and Welfare, Kamiyoga, Setagaya-ku, Tokyo 158-8501, Japan.
  • 6. School of Pharmacy, International University of Health and Welfare, 2600-1, Kitakanemaru, Ohtawara, Tochigi 324-8501, Japan.
  • 7. Faculty of Pharmaceutical Sciences, Teikyo University, Itabashi-ku, Tokyo 173-8605, Japan. Electronic address: [email protected].
PMID: 28610975 DOI: 10.1016/j.bmcl.2017.06.015
Abstract

Here we report the synthesis of new PNA monomers for pseudocomplementary PNA (pcPNA) that are fully compatible with standard Fmoc chemistry. The thiocarbonyl group of the 2-thiouracil (sU) monomer was protected with the 4-methoxy-2-methybenzyl group (MMPM), while the exocyclic amino groups of diaminopurine (D) were protected with Boc groups. The newly synthesized monomers were incorporated into a 10-mer PNA oligomer using standard Fmoc chemistry for solid-phase synthesis. Oligomerization proceeded smoothly and the HPLC and MALDI-TOF MS analyses indicated that there was no remaining MMPM on the sU nucleobase. The new PNA monomers reported here would facilitate a wide range of applications, such as antigene PNAs and DNA nanotechnologies.

Keywords
Antigene; Peptide nucleic acid; Pseudocomplementary; Strand invasion.
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