Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers

Zoltán Timár, Lajos Kovács, Györgyi Kovács, Zoltán Schmél

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The chemical synthesis of polyamide (peptide) nucleic acid (PNA) monomers 22-25 has been accomplished using Fmoc [N-(2-aminoethyl)glycine backbone], anisoyl (adenine), 4-tert-butylbenzoyl (cytosine) and isobutyryl/ diphenylcarbamoyl (guanine) protecting-group combinations, thus allowing oligomer synthesis on both peptide and oligonucleotide synthesizers. An alternative method for the preparation of (N6-anisoyladenin-9-yl)acetic acid 7 is described using partial hydrolysis of a dianisoylated derivative. Different methods were studied for guanine alkylation including (a) Mitsunobu reaction; (b) low-temperature, sodium hydride- and (c) N,N-diisopropylethylaminemediated alkylation reactions to give preferentially N9-substituted derivatives. Empirical rules are proposed for differentiating N 9/N7-substituted guanines based on their 13C NMR chemical-shift differences.

Original languageEnglish
Pages (from-to)19-26
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number1
Publication statusPublished - Dec 1 2001

ASJC Scopus subject areas

  • Chemistry(all)

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