A Practical and Efficient Approach to PNA Monomers Compatible with Fmoc-Mediated Solid-Phase Synthesis Protocols

Andrea Porcheddu*, Giampaolo Giacomelli, Ivana Piredda, Mariolino Carta, Giammario Nieddu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A straightforward synthesis of orthogonally protected PNA monomers is described. Protected aminoethylglycine (Aeg) monomers were efficiently prepared by reductive amination of N-Fmoc-glycinaldehyde with glycine methyl ester and the subsequent acylation of the free amine with N-bis-Boc-protected nucleobase acetic acids. The exocyclic amine group of the nucleobases, including the notoriously difficult-to-protect guanine nucleobase, was protected with a bis-Boc carbamate group; this increased the solubility of the nucleobases in the most common organic solvents. The current protocol allows all Aeg monomers to be prepared on both the micro- and macroscale, which avoids or minimizes the use of toxic reagents or solvents, and moreover, cheap starting materials are used. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

Original languageEnglish
Pages (from-to)5786-5797
Number of pages12
JournalEuropean Journal of Organic Chemistry
Issue number34
DOIs
Publication statusPublished - Dec 2008

Keywords

  • Peptide nucleic acids
  • Guanine
  • Protecting groups
  • Solid-phase synthesis
  • PEPTIDE NUCLEIC-ACIDS
  • PROTECTING-GROUP STRATEGY
  • POLYAMIDE
  • ALCOHOLS
  • THYMINE
  • ANALOGS
  • GUANINE
  • DNA
  • OLIGOMERIZATION
  • DEPROTECTION

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